The Midland Section of the

American Chemical Society

P R E S E N T S T H E

73rd Fall Scientific Meeting

October 21, 2017

ABSTRACT BOOK

Conference Schedule

Oral Presentations

Robertson, Philip Keynote Speaker

Climate change and agriculture: it’s not just about adaptation

Rohrssen, Megan Invited Speaker

Chemistry Rocks: Organic compounds preserved in rocks provide insight into Earth history

DeMattei, Cordell Invited Speaker

Water Chemistry From A Brewer’s Perspective

Schrenk, Matt Invited Speaker

Using DNA Sequences to Unravel Biogeochemical Processes in Groundwater Microbial Ecosystems

Host, Jon Invited Speaker

Siemens Polycrystalline Silicon: Microstructure and more

Malotky, David Aqueous high solids, low viscosity composite dispersions

Desislava, Dikova Investigations into sensitizing GaP photocathodes with CdSe quantum dots

Uyen, Hyunh Platinum(II) Prodrugs from Glycerol/ Adipic Acid Hyperbranched Poly(ester)s

Ostrander, Eric Thermal and Flammability Properties of DGEBA Epoxy Blends with Phosphorus Derivatives of Methyl 3,5-Dihydroxybenzoate

Schedule Location

7:30 Guest check in at the front desk, breakfast and coffee served Registration Desk 8:20 Opening Remarks Banquet Room B

8:30 Invited speaker (Megan Rohrssen) Banquet Room B

9:00 Invited speaker (Cordell DeMattei) Banquet Room B

9:30 Invited speaker (Matt Schrenk) Banquet Room B

10:00 Invited speaker (Jon Host) Banquet Room B

10:30 BREAK Banquet Room B

10:50 Oral Presenter (David Malotky) Banquet Room B

11:10 Oral Presenter (Dikova Desislava) Banquet Room B

11:30 Oral Presenter (Hyunh Uyen) Banquet Room B

11:50 Oral Presenter (Eric Ostrander) Banquet Room B

12:10 LUNCH Banquet Room B

1:30 Poster Session Banquet Room A

3:00 Keynote Speaker (Philip Robertson) Banquet Room B

4:00 Award Ceremony Banquet Room B

4:30 Closing Remarks Banquet Room B

Poster Presentations

1 Dilling, Wendell Method for Von Baeyer Naming of Polycyclic Cage-Shaped Hydrocarbons – Applications to Bishomocubanes

2 Dilling, Wendell How to Report Results of ACS Preferential Elections

3 Danielson, Noah Chemoenzymatic Synthesis and Evaluation of 5-Deoxy-Thio-D-Trehalose as a Trehalase-Resistant Trehalose Surrogate

4 Gorin, Craig Advanced Polymer Materials for Additive Manufacturing

5 Liu, Junying Highly Transparent Durable Superhydrophobic Coating

6 Nyutu, Edward Feasibility Study of Supported Mono-/ Multimetallic Transition Metal Silicides in Catalytic Hydrodesulfurization (HDS) of Thiophene

7 Jones, Mary Rheological Method Development: Polymer Designs for Blow Molded, Automotive Seatbacks

8 Smith, Patrick Hyperbranched Poly(ester)s for Sustained Delivery of Small Molecule Therapeutics

9 Kline, Jessica Novel Compounds for Use in Redox Flow Batteries

10 Fhaner, Matthew Investigation of Antioxidant Butylated Hydroxytoluene, Rosemary Extract, and Sesamol Using Square-Wave Voltammetry

11 Groenevelt, Jessica Concise Chemoenzymatic Synthesis of Trehalosamine, an Aminoglycoside Antibiotic and Precursor to Mycobacterial Imaging Probes

12 Alam, Shah Spectroscopic and liquid chromatographic analysis of craft brewed beers

13 Huynh, Uyen Quantitative Analysis of Beers from Mountain Town Brewing Company

14 Ford-Thompson, Naria Forensic Science: Introductory Methods and Instrumentation

15 Bowers, Elizabeth

Collaborative classroom-embedded environmental research: Three institutions working together to transform STEM courses

16 Kwiatkowski, Katie

Synthesis of C-Glycosides as Possible Type II Diabetes Treatments

17 Martinez, Darla

Functionalizing Cellulose with Added Amines to Remove Phosphates from Waterways

18 Young, Jeanette Mid-Michigan Technician Group (MMTG)

19 Burkholder, Alexander

Phase Controlled Production of Zirconium Dioxide by Hydrothermal Synthesis

20 Keel, Katarina

Oxidative rearrangement of amidine and ketone to produce imidazoline scaffolds for proteasome modulation

21 Congram, Spenser

Experimental Formation of Carbonaceous Chondrite Analogs

22 Hill, Victoria A Phosphorus-containing Diol from Itaconic Acid

23 Kendahl, Oberdorfer

Flame retarding properties of phosphorous esters of gallic acid

24 Azeez, Terick Mechanism For Inhibition of Monoamine Oxidase

25 Frantz, Nathan

A Novel Microfluidic Device for the Individual Electrochemical Assessment of Complexes within the Electron Transport Chain.

26 Jones, Corey

Discovery, Structure Activity Relationship, and Proposed Binding Mode of Human Proteasome Activators

27 Hockemeyer, Amber

The Effect of Temperature on the Growth of p-type and n-type Silicon nanowires

28 Mann, Shane

Removal of Zinc from Water Utilizing Pressure Stable, Imprinted Polymers

29 Banahene, Nicholas

A Trehalose Monomycolate Analogue Containing a Cleavable Biotin Affinity Tag for Labeling and Identifying O-Mycoloylated Proteins in Corynebacterineae

30 Alrubayyi, Aeshah Pentaethryitol Esters Containing Aryl Groups

31 Fulco, Harrison Properties of Phosphorous Esters of Diphenolic Acid

32 Patel, Arti

Exploring the coordination mode and redox properties of d8-metal hydroxamate complexes

33 Ross, Brad

Synthesis, characterization, electrochemical, and spectroelectrochemical investigation of Group 8 metal-hydroxamate complexes

34 Flores, Vincent

Electrochemical Investigation of ruthenium complexes utilizing cyclic voltammetry

35 Lienhart, Gavan

Synthesis and properties of 1-dopyl-1,2-(4-hydroxyphenyl)ethene

36 Peters, Stephan

Classroom Embedded Research: Water Analysis to Determine the Health of the Chippewa River

37 Shah, Alam

Fabrication and Evaluation of Surface Enhanced Raman Scattering Substrates of Gold Nanoparticles Embedded in a Polymer Matrix

38 DeHart, Luke

Investigating the Potential of Silver Hydroxyapatite as an Implant Coating for Preventing Prosthetic Joint Infection

39 Malczewski, Regina

STEM Outreach from Midland ACS--A Variety of Approaches for Diverse Audiences

40 Malczewski, Regina

An "Explosion" of Learning: Experiences at Midland High School with Lessons on Pop and Mentos

Oral Presentation Abstracts

Chemistry Rocks: Organic compounds preserved in rocks provide insight into Earth history

Megan Rohrssen

Assistant Professor in Earth and Atmospheric Sciences, Central Michigan University

In the 1920's Alfred Treibs identified chlorophyll-derived porphyrins in oils and triggered development of a new field of research: organic geochemistry. Today, organic geochemists find oil, test hypotheses about past ecosystems, quantitatively reconstruct past climate and more by investigating the durable natural products preserved in sediments, rocks, and oils. In this presentation, I will introduce you to the field of organic geochemistry (because Chemistry Rocks!) and provide an example from my research into the importance of methane cycling in ~50 million year old freshwater ecosystems.

Water Chemistry From A Brewer’s Perspective

Cordell DeMattei Director of Fermentation Science, Central Michigan University

Traditionally, breweries produced a single or very limited number of styles of beer. This was due, in a large part, to the chemistry of the regional water supply and its effects throughout the brewing process. Today’s craft breweries produce a diverse array of beer styles while still constrained to the chemistry of their regional water supply. This makes understanding and ability to manipulate water chemistry important for modern brewers not only to replicate traditional styles but also to ensure that they are using ingredients efficiently to produce a great product. Using DNA Sequences to Unravel Biogeochemical Processes in Groundwater Microbial Ecosystems

Matt Schrenk Assistant Professor, Department of Earth and Environmental Sciences and the Department of Microbiology and

Molecular Genetics, Michigan State University

Groundwater flow pathways disperse microbial cells, energy sources, and nutrients in fundamentally different ways than what occurs in the surface world. Most studies of groundwater have focused upon the movement of pathogens or the role of microorganisms in impacting the mobility or biodegradation of contaminants. Increasingly, the ecology and evolution of microbial communities in pristine groundwater environments have begun to be investigated. These studies are enabled by the rapid development of high throughput sequencing approaches and bioinformatics tools to tackle the immense data sets that are generated, which together provide unprecedented resolution and insight into the diversity and distribution of microbial activities.

Over the past several years, my laboratory has investigated microbial communities in fractures and pore spaces of rocks from the deep Earth. Although we have been unable to domesticate many of these organisms for growth in the laboratory, through the extraction and sequencing of their genomic DNA we have been able to demonstrate that they use energy sources (hydrogen, methane) originating in the deep subsurface and we have mapped how these properties vary both locally and globally. We can couple this detailed record of the metabolic potential of groundwater ecosystems with process-based measurements of gas flux and models of fluid transport. Recently, we have engaged in the study of native groundwater in the State of Michigan, where we are attempting to link deep and shallow fluid circulation pathways with microbial population structures and evolutionary processes. This presentation will highlight some of the recent advances we have made in using next generation sequencing approaches to elucidate biogeochemical processes in groundwater, and highlight future directions that this work is taking as we gather more information and refine our models.

Siemens Polycrystalline Silicon: Microstructure and more

Jon Cleland Host Dow Corning

Though high purity silicon electronics pervades our world, few of us are aware of the microscopic beauty and symmetry these silicon crystals show during their manufacture. Though practically all silicon has the basic diamond cubic atomic structure, the Siemens process, which nearly all electronic silicon chips begin with, produces a much more complicated microstructure at the size scales above the level of the unit cell. While some of the features seen are common in Materials Science, many are rare, including mutually annihilating sigma boundaries, grain centers of growth, and widely divergent sizes of areas of near-perfect crystallinity. The wide diversity of these features change at different rates with annealing, and thus can be used to approximate the thermal history of the sample based on the current microstructure as compared to the starting state - with more accuracy than when using the more simple microstructure of a conventional metal such as nickel. Outside the bulk of the silicon log, the same atomic forces that give rise to the complex microstructure can also give rise to unusual surface features, even in the absence of significant amounts of impurities. All of these features are destroyed by melting during the fabrication of silicon chips, but they are preserved for you to see in this presentation. Aqueous high solids, low viscosity composite dispersions

David Malotky Core R&D, Formulation Sciences, The Dow Chemical Company

A composite dispersion can be created by using a first aqueous dispersion to emulsify a second immiscible phase. By controlling the ratio of the particle sizes of the two immiscible phases to enable more efficient packing it is possible to generate a composite dispersion with high solids and low viscosity, as low at 10,000 cP at 70% volume internal phase. These composite dispersions can be valuable for waterborne applications where minimal shrinkage upon drying is desired, such as coatings, adhesive caulks, and sealants.

Investigations into sensitizing GaP photocathodes with CdSe quantum dots

Desislava R. Dikova, Molly M. MacInnes, Sudarat Lee, and Stephen Maldonado University of Michigan – Ann Arbor, Department of Chemistry

Quantum dots (QDs) have gained interest due to their interesting and highly tunable optoelectronic properties. In particular, CdSe QDs have widespread applications including biological fluorescence, LEDs, lasers, and solar cell sensitization.

The purpose of this project is to photosensitize single crystal GaP photocathodes with CdSe QDs possessing a larger band gap than that of GaP. Sensitizing a solar cell surface is a relatively cheap way to increase the efficiency of the cell, by generating more power than unsensitized cells. Additionally, as a polycrystalline material, GaP is inherently more expensive than Si solar cells, so increasing GaP efficiency is a step towards implementing it as a commercial solar cell.

In this work, CdSe QDs of varying sizes have been synthesized using a highly reproducible procedure. The quality of the QDs and their physisorption onto GaP have been monitored using fluorimetry, uv-vis absorption spectroscopy, x-ray photoelectron spectroscopy, and transmission electron microscopy.

During the synthesis process, CdSe QDs are capped with long, insulating ligands; the ligand exchange is a crucial aspect of facilitating charge transfer between QDs and GaP. Ligand exchange methods are investigated in this work; however, photosensitization has not yet been observed. Further study will be conducted on depositing a usefully thick layer of QDs that doesn’t insulate or protect the GaP surface, using different ligands or a ZnSe shell.

Platinum(II) Prodrugs from Glycerol/ Adipic Acid Hyperbranched Poly(ester)s

Uyen Huynh and Bob Howell Central Michigan University, Department of Chemistry and Biochemistry

Organoplatinum antitumor compounds played an important role in the treatment of various types of cancer. Three of the most effective organoplatinum drugs available commercially and are widely used against this disease are Cisplatin, Oxaliplatin and Carboplatin. These early platinum(II) compounds contain two inert cis ligands and to labile cis ligands that are necessary for the hydrolysis and binding to adjacent guanine units on DNA molecules. Unfortunately, administration of these compounds in human body is accompanied with rather severe side effects including nausea, vomiting and kidney damage. Poor water solubility and dose-limiting side effects are the major drawback of these organoplatinum drugs. To minimize the harmful effects, platinum drugs must be delivered at low concentration so that antitumor activity is maintained while threshold for toxicity is not reached. Platinum(II) end-capped glycerol/ adipic acid hyperbranched polyester(s) have been prepared to provide a suitable delivery system. These compounds are water soluble and contain releasable platinum moieties as an integral part of the structure.

Thermal and Flammability Properties of DGEBA Epoxy Blends with Phosphorus Derivatives of Methyl 3,5-

Dihydroxybenzoate

Eric Ostrander Central Michigan University, Department of Chemistry and Biochemistry

Polymeric materials must be flame retarded for most applications. Aromatic compounds containing some level of phosphorus are effective flame retardants. A series of compounds derived from methyl 3,5-dihydroxybenzoate have been prepared, characterized and thermal methods examined for flame retardancy in DGEBA epoxy resin systems. Climate change and agriculture: it’s not just about adaptation

Philip Robertson Distinguished Professor of Ecosystem Science in the Dept. of Plant, Soil and Microbial Sciences, Michigan State

University

Climate change will bring both well-recognized and surprising challenges to agricultural production, forcing farmers to adapt to new normals, including the growing prevalence of extreme events – indeed, farmers in the Midwest and upper Great Lakes are already adapting. Changes to water and biogeochemical cycles are among those most apparent, with pest issues close behind. But on the flip side is the opportunity for agriculture to help mitigate climate change – to abate the global atmospheric increase in greenhouse gases. Annual cropping systems offer management opportunities that can make them not just carbon neutral but carbon negative. And future bioenergy cropping systems can be surprisingly beneficial with proper attention to crop choice, management, and placement. Agriculture has substantial opportunities to participate in climate mitigation, largely underappreciated.

Poster Presentation Abstracts

50th American Chemical Society Central Regional Meeting

2019 CERM Organizing Committee

The 2019 ACS 50th annual Central Regional Meeting will be a premier meeting of the chemical sciences featuring a

convergence of global leaders in chemistry and its many impacted fields to exchange ideas, share knowledge,

celebrate and promote the enduring benefits of Chemistry for Life®. The event will be held in Midland, Michigan

starting June 4, 2019 with technical programming, and offering educator-focused events going into the following

week. Hosted by the Midland Section of the ACS, this unique event will feature leading keynote speakers and

thematic symposia assembled around the theme Molecules to Materials: chemistry in everyday life. The 2019

meeting also commemorates the 100th Anniversary of the Midland ACS section, which was established by William

J. Hale and first Chaired by Herbert H Dow, the founder of The Dow Chemical Company. Located in one of the

commercial hubs of the industrially-rich ACS Central Region, this event will draw strong participation from

industry and will promote collaboration and interactions among students, faculty, researchers and prospective

employers from industry, academia and government labs in a more intimate setting than national meetings.

The program of this meeting has three key elements:

1. World-class technical symposia spanning the full range of chemical and materials sciences

2. The confluence of industrial and educational leadership focused on inspiring and engaging younger

generations while arming them with the skills and capabilities to solve complex problems, and inspiring

policies and funding for integration of STEAM (science, technology, engineering, arts and math) in our

education system.

3. Forging partnerships within our community that celebrate chemistry in everyday life, offering the general

public an opportunity to participate in events that showcase the role of chemistry in art, forensics,

transportation, and sustainable building practices, delivered by world-renowned notable and invited

speakers.

#1 Method for Von Baeyer Naming of Polycyclic Cage-Shaped Hydrocarbons –

Applications to Bishomocubanes

Wendell L. Dilling, Anton W. Jensen, Tianzuo Xu, Jing Liang, and Linlin Zhao Department of Chemistry and Biochemistry, Central Michigan University, Mt. Pleasant, Michigan

Originally Eckroth (J. Org. Chem. 1967, 32, 3362-3365; J. Chem. Educ. 1993, 70, 609-611), and more recently extended by Zhang and coworkers [Daxue Huaxue (Univ. Chem.) 2014, 29, No. 3, 35-40] have developed a simplified method for Von Baeyer naming of polycyclic cage-shaped hydrocarbons by converting the three-dimensional structures into two-dimensional structures by expanding one ring and keeping the other atoms inside that ring. We have applied this method to the five bishomocubanes. For example 1,3-Bishomocubane (below) is named pentacyclo[5.3.0.02,5.03,9.04,8]decane.

#2 How to Report Results of ACS Preferential Elections

Wendell L. Dilling Department of Chemistry and Biochemistry, Central Michigan University, Mt. Pleasant, Michigan

The results of the recent ACS election (C&EN, Nov. 7, 2016, p 7) reported vote counts for elections of President-Elect, Directors of Districts II and IV, and one of the Directors-at-Large (Schulz). The vote count/s for the election of the other Director-at-Large (Phillips) was not reported. This election of Directors-at-Large is one that involves the recently enacted preferential voting procedure because two candidates were elected. The vote counts for the three rounds of vote counting that are shown in C&EN show how Schulz was elected by a majority of the voters, but the following steps showing how Phillips was elected are not shown. The next step in the vote counting should involve adding the second-choice votes on the ballots where Schulz was the first-choice to the first-choices for the three remaining candidates. Subsequent steps, if needed, would show how one of the three remaining candidates (Phillips) achieved a majority of the votes. Problems with reporting the results of other ACS preferential elections are shown and discussed.

#3 Chemoenzymatic Synthesis and Evaluation of 5-Deoxy-Thio-D-Trehalose as a Trehalase-Resistant Trehalose

Surrogate

Noah Danielson and Benjamin Swarts Department of Chemistry and Biochemistry, Central Michigan University, Mt. Pleasant, Michigan Trehalose, a non-reducing disaccharide composed of two glucose units, is broadly used in the food, cosmetics, biotech, and pharmaceutical industries due to its exceptional biopreservation properties. In addition, due to its autophagic induction properties, trehalose has recently gained traction as a potential therapeutic due to its ability to mitigate disease burden in animal models of metabolic disease and neurodegeneration. However, trehalose can be efficiently broken down by the enzyme trehalase, which allows microorganisms to use trehalose as a food source and potentially contaminate trehalose-containing products. Furthermore, humans possess trehalase in the kidneys and intestinal tract, which could degrade and ultimately limit the effectiveness of trehalose when administered as a therapeutic. 5-Deoxy-5-thio sugars have previously been shown to be resistant to glycosidase-catalyzed hydrolysis, leading us to hypothesize that 5-deoxy-5-thio-D-trehalose may serve as a trehalase-resistant surrogate for trehalose that could be applied in situations where trehalose breakdown is a concern. Here, we report the one-step chemoenzymatic synthesis and conformational analysis of 5-deoxy-5-thio-D-trehalose, as well as progress toward its evaluation in trehalase degradation assays.

#4 Advanced Polymer Materials for Additive Manufacturing

Craig Gorin Formulation Sciences Core R&D

3D-Printing, or additive manufacturing, is a rapidly growing market. There is a need to develop new materials to meet a broad range of applications. Dow has been working on unique polymer materials that can be used in a variety of types of 3D-printing. These include a water soluble support material, polyolefin materials for 3D-printing, and elastomeric materials including organic and silicone elastomers.

#5 Highly Transparent Durable Superhydrophobic Coating

Junying Liu Dow Performance Silicones

A simple yet inexpensive method for creating hydrophobic coatings with good durability and transparency has been developed. These hydrophobic coatings are comprised of: a pre-aggregated nanoparticle layer to provide the morphology required to obtain high water contact angle; a silsesquioxane binder layer and/or adhesive layer to provide mechanical stability; and a PFPE silane layer to lower the surface energy. The process to produce hydrophobic coatings has been developed using spray coating technology, which can be used for large scale processes with high efficiency.

#6

Feasibility Study of Supported Mono-/ Multimetallic Transition Metal Silicides in Catalytic

Hydrodesulfurization (HDS) of Thiophene

Edward K. Nyutu, Garrett Rockwell, Robert Larsen, Vasgen Shamamian Dow Performance Silicones

Catalytic hydrodesulfurization (HDS) is critical step in the industrial processing of crude oil into useful hydrocarbon products. Petroleum feedstocks have many sulfur-containing compounds, which must be removed before use because of the environmental regulations which have become more stringent in recent years. The development of highly active and sulfur-tolerant catalysts for hydrodesulfurization (HDS) is of great significance in petroleum refining. Here, we explored the initial processing, characterization, and catalytic activity screening for hydrodesulfurization (HDS) of thiophene by bulk metal silicides and supported silicidated mono-/multi-metallic intermetallic catalyst compositions. Most of the bulk silicides were obtained from commercial vendors, while supported silicidated catalyst compositions were processed in-house via the incipient wetness impregnation method and silicidation in a chemical vapor infiltration reactor. Catalytic activity for thiophene HDS was screened internally using a flow-reactor and benchmarked with a commercial formulation (14Mo-3.5Co/γ-Al2O3) and, where applicable, with corresponding calcined oxide-based compositions. Differing levels of catalytic activity were observed for various unsupported and supported mono/-multimetallic silicide compositions. For silicidated supported metal-based catalysts, silicidation temperature had a significant effect on catalytic activity, with low-to-medium silicidation temperatures proving much more effective than high temperatures for yet to be established reasons. Silicidation of supported metal catalysts generally lead to lower activity than oxidation. A notable exception is the silicidated 20W1-x-5Cox-Si2/γ-Al2O3 catalyst, which reached much higher thiophene conversion levels than its oxidized counterpart. Initial high HDS activities of oxide-based metal catalysts is well known, however oxide-based catalysts are reported to deactivate rapidly with time in HDS conditions. Further work is required to determine the structure and the long-term stability (time-on-stream) of the developed silicidated HDS catalysts.

#7 Rheological Method Development: Polymer Designs for Blow Molded, Automotive Seatbacks

Mary Ann Jones, James Seliskar, Stephane Costeaux, and Bob Donald Analytical Sciences, DowDupont

The automotive industry has been seeking to create lighter weight vehicles for improved fuel economy through the replacement of metal with plastic in the vehicle. One such project involved the development of an all plastic, blow molded seatback that would be fabricated in an extrusion, blow molding process. The part was required to pass a European based dynamic luggage retention test. The polymer also needed to have an extreme amount of melt strength such that a 30 pound parison could be hung in the blow molding process. Increases to melt strength through molecular weight change also increase polymer viscosity. High viscosity leads to shear heating, resulting in a loss of melt strength as temperature increases. Parison shrink or draw-up from strain recovery in a high molecular weight melt can lead to higher weight parisons and failure in the molding process. This poster describes the rheological analysis approach used to balance melt strength with viscosity, and ultimately with ductility to successfully blow mold very large parts.

#8 Hyperbranched Poly(ester)s for Sustained Delivery of Small Molecule Therapeutics 1Daniel Zhang, 1Brandon Zhu, 2Tom Chamberlin, 3Tracy Zhang and 3Patrick Smith 1H.H. Dow High School, Midland, MI; 2Dendritech, Inc., Midland, MI; 3Michigan State University St. Andrew, Midland, MI

Active ingredients in medicinal applications and agriculture are often administered in excess due to ineffective utilization of the actives. The challenge is how to increase the efficiency of active utilization, thereby reducing side effects and contamination to the environment. Designing smart delivery systems which are capable of controlled release of the actives is one route to increasing efficiency. Hyperbranched polymers are well suited for controlled delivery because they are polymeric materials with molecular architectures providing the highest branching density of any polymeric material as well as the highest molecular end group density. Biodegradable hyperbranched polyesters (HB-PEs), with either hydroxyl or carboxyl end-groups, have been prepared from biosourced di-functional acids and tri- or tetra-functional alcohols by utilizing the bimolecular non-linear polymerization methodology. Active ingredients are chemically bonded to the HB-PEs and then released to the original forms through hydrolytic degradation of the polymer conjugate, either enzymatically or chemically.

#9 Novel Compounds for Use in Redox Flow Batteries.

Jessica Kline, Ethan Bruce, Adina Dumitrascu Michigan State University, Midland

Finding the energy to power human civilization while preserving the environment, is the greatest challenge humanity faces this century. While many sources of energy are yet to be fully harnessed, energy storage is the biggest roadblock to widespread adoption of renewable energy. Redox flow batteries (RFB) represent a class of electrochemical energy storage devices. The name “redox” refers to the chemical reduction and oxidation reactions employed in RFBs to store energy in liquid electrolyte solutions which then flow through a battery of electrochemical cells during charge and discharge. RBFs could one day usher in widespread use of renewable energy, but only if the devices can store large amounts of energy cheaply and independently of weather-based power sources. RFBs are attractive for grid storage applications because they are relatively inexpensive and highly scalable. For a given chemistry, the power output of the RFB is largely defined by the flow cell characteristics, while the energy storage capability depends primarily on the size of the storage tanks. Thus, increasing the energy storage capacity of an RFB is as simple as building bigger tanks. Unfortunately, there are several challenges to the widespread adoption of RFBs in grid storage applications. The biggest hurdles are associated with the need for an ion-selective membrane, which often represents the most expensive RFB component. In addition to high costs, the efficiency of commercial membrane materials is less than ideal, leading to a slow cross-contamination of the anolyte and catholyte solutions. Finally, the membrane tends to be fragile and subject to a gradual decline in performance, and thus regular maintenance and/or replacement is required. Recently, organic based energy storage systems show potential for overcoming the current limitations of RFBs and provide many new opportunities for their application. Organic compounds described in this poster can serve as building blocks for new materials in non-aqueous RFBs that promise to provide long service lifetimes with reasonably high voltages (2.2 V or higher) at very low cost.

#10 Investigation of Antioxidant Butylated Hydroxytoluene, Rosemary Extract, and Sesamol Using Square-Wave

Voltammetry Robert J. Ruddy, Katelyn A. Keene, Matthew J. Fhaner Department of Chemistry and Biochemistry, University of Michigan – Flint, Michigan, 48502

In recent years, consumer demand for natural ingredient in consumer products has caused traditional synthetic antioxidants such as butylated hydroxytoluene (BHT) to be replaced by naturally derived species such as tocopherol or rosemary extract (RE)[1]. As a result, a push has been made to investigate novel species as potential antioxidants[2]. The increased interest in screening antioxidants has led to a number of different methodologies for investigating antioxidant levels including High Performance Liquid Chromatography, Ferric Reducing Ability Plasma assays, Trolox Equivalent Antioxidant Capacity assays, and more recently, electrochemical techniques. Previous work in our group has focused on electrochemical detection for more routine analysis of antioxidant species[3]. This is due to the low detection limits, consumable costs, reduced waste, and fast analysis times. Specifically, voltammetric techniques have been utilized to obtain quantitative and qualitative data for antioxidants, however the species investigated were primarily previously studied systems[4, 5]. This work focuses on investigating more novel systems in comparison to industry accepted systems such as BHT and RE. In our work we provide preliminary studies on determining limits of detection, lower limits of quantitation, and oxidation potentials for BHT, RE, and the novel antioxidant sesamol, which was previously shown to be a quality antioxidant system for omega-3 fatty acids substrates. 1. Guitard R, Paul JF, Nardello-Rataj V, Aubry JM (2016) Myricetin, rosmarinic and carnosic acids as superior

natural antioxidant alternatives to α-tocopherol for the preservation of omega-3 oils. Food Chem 213:284–295. doi: 10.1016/j.foodchem.2016.06.038

2. Fhaner M, Hwang H-S, Winkler-Moser JK, et al (2016) Protection of fish oil from oxidation with sesamol. Eur J Lipid Sci Technol 118:885–897. doi: 10.1002/ejlt.201500185

3. Lubcekyj RA, Winkler-Moser JK, Fhaner MJ (2017) Application of Differential Pulse Voltammetry to Determine the Efficiency of Stripping Tocopherols from Commercial Fish Oil. J Am Oil Chem Soc 1–10. doi: 10.1007/s11746-017-2968-0

4. S.-C. Litescu G-LR (2000) Estimation of the antioxidative properties of tocopherols ± an electrochemical approach. Eur Food Res Technol 211:218–221. doi: 10.1007/s002170050027

5. Galeano Diaz T, Durán Merás I, Guiberteau Cabanillas A, Alexandre Franco MF (2004) Voltammetric behavior and determination of tocopherols with partial least squares calibration: Analysis in vegetable oil samples. Anal Chim Acta 511:231–238. doi: 10.1016/j.aca.2004.02.010

#11

Concise Chemoenzymatic Synthesis of Trehalosamine, an Aminoglycoside Antibiotic and Precursor to

Mycobacterial Imaging Probes

Jessica Groenevelt Department of Chemistry and Biochemistry, Central Michigan University, Mt. Pleasant, Michigan

Trehalosamine (2-amino-2-deoxy-α,α-D-trehalose) is an aminoglycoside with antimicrobial activity against Mycobacterium tuberculosis, and it is also a versatile synthetic intermediate that has been used to access imaging probes for mycobacteria. Published chemical syntheses of trehalosamine are generally lengthy and/or low-yielding. Here, we report an efficient 2-step chemoenzymatic synthesis of trehalosamine (63% overall yield) that features trehalose synthase (TreT)-catalyzed 1,1-α,α-stereoselective glycosylation as the key transformation. We also demonstrate that chemoenzymatically synthesized trehalosamine can be readily elaborated to two complementary imaging probes, which label live mycobacterial cells via distinct metabolic pathways.

#12 Spectroscopic and liquid chromatographic analysis of craft brewed beers

Md. Shah Alam, Corey Arnett-Butscher, Jessica Betz, Elizabeth Bowers, Hannah Brinkman, Syeda Nusrat Muhith, and Dale LeCaptain Department of Chemistry and Biochemistry, Central Michigan University, Mt. Pleasant, Michigan As craft brewing continues to infiltrate the beer market, many brewers are seeking to better understand the chemistry of their products. The proximity of Mountain Town Brewing Company to Central Michigan University’s campus provides a unique opportunity for advanced analytical chemistry students to obtain a variety of beers for analysis. Here the compounds that contribute to the shelf-life, haze, and flavor of these beers will be analyzed. Hops and herbs, contain several compounds that impact these qualities. For instance, hops contribute alpha- and iso-alpha- acids, which affect the bitterness of the beer and also serve as preservatives. The concentrations of several compounds, including these bitter acids, will be measured and compared. Additionally, some samples will be force aged because free radical concentration increases over time. As the quantity of free radicals increases, flavor components break down, often resulting in an increase in haze and bitterness and a decrease in shelf-life. Electron spin resonance (ESR) will be used to measure free radicals, while a turbidimeter will be used to quantify haze. Bitterness will be examined using two methods, UV-Vis spectroscopy and HPLC with a UV detector. While bitterness is a major contributor to beer flavor, other factors such as the hardness of water used in brewing also affect taste. The divalent cations that cause water hardness will be quantified using ion chromatography. Profiles of each beer will be written using the data collected from these five methods.

#13 QUANTITATIVE ANALYSIS OF BEERS FROM MOUNTAIN TOWN BREWING COMPANY

Uyen Huynh, Amanda Nilles, Nicholas Banahene, Alex Ausmus, Amanda LyVere, Qing Qing Dong, and Dale LeCaptain Department of Chemistry and Biochemistry, Central Michigan University, Mt. Pleasant, Michigan Beers vary in flavor, color, and alcohol content. The advanced analytical chemistry course at CMU is measuring various beer samples brewed by Mountain Town brewery located in Mount Pleasant, MI. In this study, a variety of quantitative techniques were performed to analyze the different beers’ alcohol content, hardness, and calories count. Both Karl Fischer and thermogravimetric analysis (TGA) were utilized to determine the ethanol and water contents in each sample. In addition, ions such as carbonate, bicarbonate, and hydroxide contributed to the hardness of beer which may play an effect on their bitterness. We used an auto titrator to calculate the concentration of each ions and compare them to the IBU (International Bitterness Unit) values of each sample. Currently, there is not a method for the local brewery to determine their beers’ calories content. Our proposed approach uses differential scanning calorimetry (DSC). Both gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS) are used to determine the alcohol content of each beer sample using both direct injection and headspace injection.

#14 Forensic Science: Introductory Methods and Instrumentation

Naria Ford-Thompson, Dr. Melissa Strait Chemistry Department, Alma College

An investigation of introductory methods utilized in forensic science for the examination and identification of drugs and fingerprints was conducted. Household medications, chemical equivalents of synthetic drugs, and controls were used in the exploration of drug identification in conjunction with TLC, color spot testing, and IR spectroscopy. Based on Rf values, TLC was used to determine which of the controls were main ingredients in the various drugs tested. The Rf values of those tested matched that of their control ingredients with the exception of the ibuprofen tablet whose Rf value corresponded to aspirin. A presumptive drug analysis was done by color spot testing using three separate reagents: Scott, Mandelin, and Marquis. All of the specimens that reacted with the Marquis and Mandelin reagent led to a correct identification and the specimens tested with the Scott reagent were non-reactive as expected. IR spectroscopy was also used to identify unknown solutions. Each unknown compound was analyzed using IR and the spectra was compared to that of the controls to determine the composition. Ninhydrin created contrast between fingerprint residues and paper surfaces which enabled them to be visualized enough to be studied. In some cases, ZnCl2 was used in conjunction with ninhydrin to improve the quality of the prints. This investigation supported the general assumption that TLC, spot testing, and IR are all reasonable ways to determine the identification of drugs due to their ease of use and comprehension as well as their high reliability. It was also determined that using ninhydrin and ZnCl2 to reveal latent fingerprints is a plausible way to examine the prints, but additional resources would be needed for identifications. Continued work will involve using GC/MS to further analyze drugs, various reagents to test for blood presence, and microscopy to identify polymers, fibers, and hairs.

#15 Collaborative classroom-embedded environmental research: Three institutions working together to

transform STEM courses Elizabeth Bowers, Kaitlyn Klay, Dr. Janice Tomasik Department of Chemistry and Biochemistry, Central Michigan University, Mt. Pleasant, Michigan Undergraduate science laboratory experiences have come under national scrutiny over the last decade as student interest in science as an educational and career pathway has continued to dwindle. Several programs, such as the Center for Authentic Science Practice in Education (CASPiE) and the Freshman Research Initiative (FRI), based out of Purdue University and the University of Texas at Austin respectively, have sought to integrate real research experiences into the laboratory classroom as a means of engaging and retaining students within STEM (Science, Technology, Engineering, and Mathematics) majors. Since 2013, educators at Central Michigan University (CMU), Delta College, and Saginaw Valley State University (SVSU) have collaborated to implement and study the impacts of course-based undergraduate research experiences (CUREs) on chemistry and biology students at these institutions. Two survey instruments, the Science Motivation Questionnaire (SMQ) and the Awareness of Attitudes towards Environmental Issues (AAEI), were used to assess the impact of these experiences. Students were surveyed before and after completion of a lab project, whether it was a traditional lab (the control group) or a CURE (the experimental group). Presented here is a summary of the current project and the most recent evaluation results.

#16 Synthesis of C-Glycosides as Possible Type II Diabetes Treatments

Katie Kwiatkowski, Cavin Compton, Dr. Jennifer Chaytor Department of Chemistry, Saginaw Valley State University, Saginaw, Michigan

Type II diabetes mellitus is a growing problem in the world and it is characterized by hyperglycemia, or an increase in glucose levels in the blood. Individuals who suffer from this can be prescribed a healthy diet and exercise, although medication is often required to fully manage the disease. Complications from Type II diabetes are not limited to, but include cardiovascular disease, kidney failure, and neuropathy. Current medications exist to eliminate excess blood glucose, but can result in unfavorable side effects. This research focuses on the synthesis of aryl-C-glycosides which may be used to lower blood glucose levels. Two synthetic pathways are currently being explored to prepare various aryl-C-glycosides. The synthetic products are purified using techniques such as column chromatography, washes, and recrystallization. The products are analyzed using Nuclear Magnetic Resonance Spectroscopy to ensure reaction completion and accuracy. The target compounds will be evaluated using an enzymatic assay. This presentation will discuss two approaches to the synthesis of aryl-C-glycosides.

#17 Functionalizing Cellulose with Added Amines to Remove Phosphates from Waterways

Darla Martinez, Dr. Jennifer Chaytor Department of Chemistry, Saginaw Valley State University, Saginaw, Michigan/ACS Project SEED

Eutrophication is a cycle where aquatic plants over grow due to increased amounts of phosphates released into waterways. It starts when phosphates are introduced into a body of water via agricultural runoff. Aquatic plants feed off the phosphates and begin to bloom in mass quantities. This poses a problem because it reduces the amount of sunlight available to other organisms; it can also create a hypoxic environment. Ultimately this process leads to the death of many organisms. To reduce the harmful effects produced by eutrophication, cellulose was modified with added amines to potentially adsorb phosphates from the water. Cellulose was modified in two steps: tosylation and functionalization. The amines chosen were varied in order to compare the phosphate-adsorbing ability of cellulose functionalized with primary, secondary, and tertiary amines. For the functionalization reactions, we received a very small yield, and products had a gel-like appearance. Products were collected and were tested using IR (Infared) Spectroscopy to see if the amine was added to cellulose. Results from IR were promising, and many showed a possibility of an added amine. Once the desired products were isolated, they were subjected to phosphate testing. Testing showed that cellulose functionalized with diethylamine was most effective with 36% adsorption. Phosphate testing proved to be a little difficult because some of the products had such a low yield that all the product had to be used and testing could not be done more than once. To ensure the best results, phosphate removal columns were made but they gave similar results to original phosphate testing method. Additionally, we collected Phragmites as a natural source of cellulose and used it in the tosylation and functionalization reactions.

#18 Mid-Michigan Technician Group (MMTG)

Jeanette Young & Kyle Krauseneck Mid-Michigan Technicians Group (MMTG)-Affiliate of ACS

For the past twenty six years, the Mid-Michigan Technician Group has been focused on promoting personal and career related growth throughout the Technician community. Current and past members have participated in numerous public outreach events such as Kids and Chemistry, SciFest, ACS Day at the Fair, and many more. This poster presentation will cover various activities MMTG has sponsored or volunteered it’s time to, in both the science community and those interested in one day working in a science related field. Also included are various awards MMTG has received from their contribution to the community and the promotion of technicians.

#19 Phase Controlled Production of Zirconium Dioxide by Hydrothermal Synthesis

Alexander Burkholder Department of Chemistry and Biochemistry, Central Michigan University, Mt. Pleasant, Michigan Zirconium dioxide, or zirconia, is a crystalline metal oxide with unique atmospheric properties. Zirconia can have many industrial and commercial applications due to its high melting point, high ionic conductivity, optical properties, and high dielectric constant. Zirconia can occur in three distinct phases; monoclinic, tetragonal, and cubic. The synthesis of these phases has been extensively studied using a variety of synthesis methods; however, these methods often involve high temperatures, high pressures, and long reaction times. In this study, the phase controlled synthesis of zirconium dioxide by hydrothermal synthesis is presented. It was found that through hydrothermal synthesis, a relatively cost effective and time efficient method, monoclinic and cubic zirconia can be synthesized.

#20 Oxidative rearrangement of amidine and ketone to produce imidazoline scaffolds for proteasome modulation

Katarina Keel, Jetze Tepe Michigan State University, Department of Chemistry

The proteasome is an important protease in cells that degrades redundant, misfolded and damaged proteins. Proteasome inhibitors are currently used to treat multiple myeloma and relapsing mantle cell lymphoma. One of the most successful proteasome inhibitors to come from the Tepe lab is imidazoline TCH-165. While potent towards the proteasome at a subnanomolar level, TCH-165 has a higher molecular weight and lipophilicity than 80% of pharmaceuticals on the market today. This brought about a need for new, potent imidazoline scaffolds with drug-like characteristics. Through a simple, efficient, 3-step method, 5,5-disubstitued imidazolines with reduced molecular weight and lipophilicity have been produced.

#21 Experimental Formation of Carbonaceous Chondrite Analogs

Spenser Congram, Brian May Alma College, Department of Chemistry

To be comprehensive in the study of asteroid disruption modeling experiments, studies must be done on every type of meteorite. CM Carbonaceous chondrites are difficult to acquire due to their rare nature. As these meteorites are more primitive than other carbonaceous chondrites, they have key carbon and mineral characteristics. By placing the material in pressure vessels at 150°C with 0.5 M NaOH, the ordinary chondrite NWA 869 (L3-6) can be artificially hydrated to create material analogous to carbonaceous chondrites. The chemistry within the chondrules is changed: IR spectroscopy indicates more complex clays and hydrated minerals were created. After molding the hydrated carbonaceous chondrite material into an analog meteorite using a slurry of hydrated material and 0.5 M NaOH over heat, the disruption pattern of CM carbonaceous chondrite material can be reproduced without damaging the real samples. Preliminary analogs were too dense and disrupted differently, so recent work has focused on decreasing the density of the analogs without affecting the internal chemistry. This was achieved by decreasing the particle size of the hydrated material in the molding process. Previous experiments used less than 2 mm diameter particles in the molding process, while recent experiments have shown that using less than ½ mm particles decreases the density of the analog carbonaceous chondrite. The small-particle samples exhibit densities much closer to CM carbonaceous chondrite densities. Future experiments will aim to create analogs of artificially hydrated NWA 4502, a CV3 carbonaceous chondrite (an anhydrous, carbon containing sample), and disrupt those as well.

#22 A Phosphorus-containing Diol from Itaconic Acid

Victoria Hill Department of Chemistry and Biochemistry, Central Michigan University, Mt. Pleasant, Michigan Itaconic acid is a four-carbon diacid containing a methylene group at the 2-position and is readily available from biosources. Michael addition of phosphites to the methylene group provides a route to a variety of phosphorus compounds. Treatment with borane provides the corresponding diol. This compound may serve as a source for a number of compounds of interest as a polymer additive. Direct esterification or Atherton-Todd reaction provides phosphorus esters containing a high level of phosphorus.

#23 Flame retarding properties of phosphorous esters of gallic acid

Kendahl L. Oberdorfer, Bob A. Howell Department of Chemistry and Biochemistry, Central Michigan University, Mt. Pleasant, Michigan Gallic acid is a renewable biomaterial produced by a variety of plants (gallnuts, sumac). Gallic acid is a benzoic acid containing three hydroxyl groups. These properties offer the potential for conversion to a variety of phosphorus esters that may function as nontoxic flame retardants for polymeric materials. Treatment of the acid with thionyl chloride followed by aniline generates the corresponding amide. From there, the hydroxyl groups may be converted to a variety of phosphorus esters. For example, the treatment of the amide with diethyl phosphite or diphenyl phosphite in the presence of carbon tetrachloride (Atherton-Todd reaction) may be used to generate the corresponding tris-phosphate. Other phosphorus esters may be generated in a similar manner.

#24 Mechanism For Inhibition of Monoamine Oxidase Terick Azeez Department of Chemistry and Biochemistry, Central Michigan University, Mt. Pleasant, Michigan

Monoamine Oxidase (belonging to the protein Flavin family) is an enzyme that catalyzes oxidative deamination. This process is blocked by the suicide inhibitor N, N-dimethyl propargylamine, which forms a flavocyanine with the flavin at the active site of MAO. The mechanism for the inhibition reaction is not known. Our hypothesis is that the propargyl group reacts with the Flavin through an ene reaction. The propargyl group has never been shown to undergo ene reactions. We are in the process of reacting dimethyl propargyl amine and methyl propargyl ether with the enophiles PTAD, Maleic anhydride and tetraacetyl riboflavin to see if ene reactions occur between these compounds. The products are analyzed by NMR and UV. Our findings will be presented and innovative methods to help better our research.

#25 A Novel Microfluidic Device for the Individual Electrochemical Assessment of Complexes within the Electron

Transport Chain Nathan Frantz Michigan State University, Department of Chemistry

Cost of medical care for cancer and diabetic patients was approximately $157 billion in 20101, and $176 billion in 20122, respectively, in the US alone. These, and several other diseases, included in the NIH-wide strategic plan for 2016-20203, are associated with mitochondrial dysfunction4. Assessing disease-related functional changes in mitochondrial currently relies on measuring oxygen consumption rates (OCRs) catalyzed by complex IV in the electron transport chain (ETC) of the inner mitochondrial membrane. The current methods for measuring OCRs are subject to several limitations, including high sample demand, high operational costs, and, most importantly, an inability to yield direct information about upstream processes that affect OCRs. We aim to circumvent limitations of current respirometric techniques by developing a novel microfluidic/electrochemical approach that will allow for complex-specific assessment of catalytic capacity in intact mitochondria, independent of the measurement of OCRs. By using select redox mediators to shuttle electrons between the electrode and the inner mitochondrial membrane, it is possible to interact independently with, and obtain activities of, each complex within the ETC. This information will allow for a direct comparison between healthy mitochondria and mitochondria that come from tissues affected by a particular disease or a corresponding biomedical model. Preliminary data show that the novel microfluidic device can electrochemically manipulate the ETC within whole mitochondria. (1) Cancer Prevalence and Cost of Care Projections https://costprojections.cancer.gov/ (accessed Sep 29, 2017). (2) The Cost of Diabetes: American Diabetes Association® http://www.diabetes.org/advocacy/news-

events/cost-of-diabetes.html (accessed Sep 29, 2017). (3) National Institutes of Health. NIH-Wide Strategic Plan: Fiscal Years 2016-2020; 23872BC. (4) Srinivasan, S.; Guha, M.; Kashina, A.; Avadhani, N. G. Biochim. Biophys. Acta - Bioenerg. 2017, 1–13.

#26 Discovery, Structure Activity Relationship, and Proposed Binding Mode of Human Proteasome Activators

Corey L. Jones, Evert Njomen, Jetze J. Tepe* Michigan State University, Department of Chemistry

The proteasome is tasked with the clearance of damaged, misfolded, and redundant proteins from cells, an integral part of cellular homeostasis. Age related decline in this pathway leads to accumulation, and ultimately aggregation, of proteins and is implicated to be a part of the pathogeneses of numerous neurodegenerative diseases including Alzheimer’s, Parkinson’s and Huntington’s disease. Enhancement of this pathway is thus thought to be a potential treatment for these pathologies. This poster illustrates the discovery, optimization, and implications of human proteasome enhancers developed by the laboratory.

#27 The Effect of Temperature on the Growth of p-type and n-type Silicon nanowires

Amber Hockemeyer Department of Chemistry and Biochemistry, Central Michigan University, Mt. Pleasant, Michigan In this experiment, silicon nanowires are grown via a solid-liquid-solid method by coating p-type and n-type silicon wafers with a nickel catalyst. The effect of temperature on size of whisker growth was examined using transmission electron microscopy.

#28 Removal of Zinc from Water Utilizing Pressure Stable, Imprinted Polymers

Shane Mann, Travis Johnson, Evie Medendorp, Robert Ocomen, Kaityln Schwallier Department of Chemistry and Biochemistry, Central Michigan University, Mt. Pleasant, Michigan Waste water remediation is a pivotal process relied upon by untold millions across the globe. Often overlooked but problematic in high concentrations zinc is an ever-present heavy metal necessary for normal bodily function. Elevated concentrations that could induce toxicity can be found in tailings and industrial waste water. Within the Mueller research group, removal of zinc from water has been achieved through the use of zinc-imprinted, pressure-stable poly-acrylate/amide random co-polymers. Polymer stability, with regards to pressure, was enhanced through the introduction of a monomer containing a tert-butyl functional group. Polymer performance was investigated to quantify zinc uptake under pressure. By varying monomeric ratios and introducing a methylated cross-linker variant, removal rates and pressure stability were effectively quantified over a broad range of polymeric derivatives. Effluent from these studies was subjected to analysis via flame atomic absorption spectroscopy in order to monitor zinc removal. Zinc remediation was investigated in combination with calcium to further understand the competitive affects of ionic species. Water flow and ion retention time were of key interest in order to understand optimal operating condition. In order to monitor size and abundance of imprinted sites scanning electron microscopy (SEM) and porosimeter studies were performed.

#29 A Trehalose Monomycolate Analogue Containing a Cleavable Biotin Affinity Tag for Labeling and Identifying

O-Mycoloylated Proteins in Corynebacterineae

Nicholas Banahene Department of Chemistry and Biochemistry, Central Michigan University, Mt. Pleasant, Michigan

Bacteria in the Corynebacterineae suborder, including the causative agents of tuberculosis, are characterized by a unique outer membrane (mycomembrane) that is rich in mycolic acids. Biosynthesis of the mycomembrane is assisted by trehalose monomycolate (TMM). Cytoplasmic TMM is transported across the plasma membrane to the outer membrane where its mycolic acid group is transferred from TMM onto various acceptor molecules, including carbohydrates and proteins. Synthetic TMM analogues used in combination with click chemistry have exploited these mycomembrane biosynthesis pathways to enable cellular imaging of live bacteria. This approach has also been coupled with mass spectrometry to allow for the identification of proteins that are post-translationally modified by mycolic acids, i.e. O-mycoloylated proteins. However, this method could only allow analysis of low molecular weight proteins and does not allow for purification and characterization of these proteins. Here, a cleavable biotin tag linked to the TMM scaffold (O-SS-BiotinTMM) has been synthesized that will allow for one-step labeling, purification and subsequent identification and characterization of these proteins. Uptake studies of this compound in parallel to original TMM (O-AlkTMM) show that O-SS-BiotinTMM does not impair the growth of Corynebacterium glutamicum up to 1 mM. Flow cytometry studies also show that O-SS-BiotinTMM efficiently labels cells, and no signal saturation was observed up to 1 mM concentration. These findings suggest that O-SS-BiotinTMM will be a valuable tool for identifying and characterizing O-mycoloylated proteins.

#30 Pentaethryitol Esters Containing Aryl Groups Aeshah Alrubayyi Department of Chemistry and Biochemistry, Central Michigan University, Mt. Pleasant, Michigan Polymeric martials are everywhere in the developed world. For most applications these materials must be plasticized. Traditionally, phthalate esters, are the most common because of its cost and effectiveness. However, these materials may bioaccumulate enter the human diet and contribute to various negative health conditions. This is because its migrate from the host polymer. A consequence, new bio based plasticizers are being developed. Pentaethryitol esters are of interest as bio-based plasticizers from polymeric materials. A variety of pentaerythritol esters containing benzoate and thiophenecarboxylate are being prepared for examination as plasticizers form polymeric materials. The stability of this material has been evaluated using thermogravimetric and spectroscopic techniques.

#31 Properties of Phosphorous Esters of Diphenolic Acid

Harrison Fulco Department of Chemistry and Biochemistry, Central Michigan University, Mt. Pleasant, Michigan Recent concerns about sustainability and environmental quality have stimulated the development of nontoxic polymer additives. In particular, non-halogen materials which are not stable in the environment and do not bioaccumulate are being sought. Additives generated from renewable biosources are generally more biodegradable and less toxic than those generated from petroleum sources. Further, the cost of these materials is independent of fluctuations in the petrochemical markets. Flame retardants based on biomaterials are particularly attractive. Diphenolic acid is available from natural sources and contains functionality to permit conversion to a variety of phosphorous esters with flame-retarding potential. The carboxylic acid is first converted to the corresponding anilide and then treated with appropriate phosphorus reagents to generate difunctional phosphorus ester. The resulting compounds contain both phosphorus and nitrogen and should display good flame retardancy in a variety of polymeric materials.

#32

Exploring the coordination mode and redox properties of d8-metal hydroxamate complexes

Arti Patel, Andrea Nikolai, Brad Ross, and Dr. Adam Warhausen Department of Chemistry, Saginaw Valley State University, Saginaw, Michigan

The aim of this project is to gain insight in to the interactions of hydroxamic acids with biologically relevant molecules. Molecules, such as hydroxamic acids, are known donors of the important diatomic molecule nitric oxide. Our research investigates different modes of coordination of the hydroxamate to the metal. Once the new complexes have been synthesized, a large emphasis of this work focuses on understanding their redox behavior. In addition to elucidating the coordination mode of the hydroxamate to the metal, our group set out to investigate the electrochemical, and spectroelectrochemical properties of these complexes and their analogues. The redox properties of these complexes are examined through cyclic voltammetry (CV) and IR-spectroelectrochemical techniques. The results obtained from this investigation will be presented.

#33

Synthesis, characterization, electrochemical, and spectroelectrochemical investigation of Group 8 metal-

hydroxamate complexes

Brad Ross and Dr. Adam Warhausen Department of Chemistry, Saginaw Valley State University, Saginaw, Michigan

Interactions between nitric oxide and biologically available materials have been widely studied in the field of chemistry. Fortunately, there is much more to learn and to study about organic molecules that are capable of producing nitric oxide within living organisms. The nitric oxide donating molecules utilized in this research are hydroxamic acids. This project aims to study the interactions of these hydroxamic acids with iron and ruthenium- containing bimolecular models. The emphasis of this work focuses on understanding their redox behavior using electrochemical and spectroelectrochemical methods. The redox properties of these complexes and of their analogues have been examined utilizing cyclic voltammetry (CV) and IR-specechem techniques. The results of these afore mentioned studies will be presented.

#34 Electrochemical Investigation of ruthenium complexes utilizing cyclic voltammetry

Vincent Flores, John Sous, and Dr. Adam Warhausen Department of Chemistry, Saginaw Valley State University, Saginaw, Michigan

The complexes benzylidene-bis(tricyclohexylphosphine)-dichlororuthenium, and [1,3-bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro(phenylmethylene)(tricyclohexylphosphine)ruthenium are well-known and extensively studied complexes. They are known for the wide range of reactions that they can be involved in. An area of interest that lacks in current literature is the redox properties of these complexes and their analogues. Our focus is to expand the knowledge of these complexes, more specifically, with respect to their first oxidation potential. Our group set out to investigate the electrochemical, and spectroelectrochemical properties of these complexes as well as their analogues. The redox properties of these complexes have been examined utilizing cyclic voltammetry (CV) techniques utilizing various solvents and electrolytes. The extensive CV experimentation includes the utilization of screen printed platinum and glassy carbon disk electrodes, as well as varying temperatures.

#35 Synthesis and properties of 1-dopyl-1,2-(4-hydroxyphenyl)ethene

Gavan Lienhart Department of Chemistry and Biochemistry, Central Michigan University, Mt. Pleasant, Michigan As the potential health risks associated with the use of organohalogen flame retardants become more apparent, the need to develop new, effective and nontoxic alternatives becomes increasingly urgent. Organophosphorus compounds offer a promising opportunity for replacement. Functionalization of desoxyanisoin with 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO) in the presence of an acid followed by cleavage of the methyl groups with high temperature pyridine hydrochloride affords 1-dopyl-1,2-(4-hydroxyphenyl)ethene. This diol can be further functionalized with additional phosphorus containing groups to create high phosphorus content additives. Alternatively, it may be used as a monomer in the creation of new polymers. These materials may serve as flame retardants in a variety of polymeric systems.

#36

Classroom Embedded Research: Water Analysis to Determine the Health of the Chippewa River

Stephen Peters Central Michigan University / Chemistry Education

During the Fall of 2016 and Spring of 2017 chemistry students at Central Michigan University in General chemistry and Quantitative Analysis performed an experiment where they were tasked with running analysis on water samples taken from two different locations on the Chippewa river. In both classes the main purpose was to see if water condition in the river were at healthy levels. This experiment serves as a way to expose first year students to research, while utilizing student results to assess the health of the Chippewa river. In the quantitative analysis class, student testing can become more precise, but ultimately leads to the same goal of monitoring the overall health of the river. Currently, this research seeks to determine how student learning and attitudes are affected by incorporation of these activities into the chemistry classroom. Additionally, we wished to determine the extent to which the student environmental research results were valid. To help test the validity of the results collected by the students, a standard water sample was developed. The students tested this sample believing it came from a third site on the river. Student results were then compared to known results for the standard sample. Results were collected during each general chemistry section, then compiled and passed along to the Quantitative Analysis students. The massive collection of general chemistry student data was then analyzed by the quantitative analysis students.

#37 Fabrication and Evaluation of Surface Enhanced Raman Scattering Substrates of Gold Nanoparticles

Embedded in a Polymer Matrix Md. Shah Alam and Mary M. J. Tecklenburg Department of Chemistry and Biochemistry, Central Michigan University, Mt. Pleasant, Michigan The objective of this study is to fabricate a reproducible and stable substrate for surface enhanced Raman scattering (SERS), which measures the increased Raman scattering of a molecule adsorbed on or in proximity to a nanostructured metal surface. To accomplish the purpose, preparation of reproducible AuNPs of similar size and shape as well as narrow size distribution were required. The structural features of AuNPs influence strongly the strength of enhancement of Raman scattering by a molecule of interest. Stability of the nanoparticles for SERS was evaluated by incorporating gold nanoparticles into a polymer matrix (branched polyethyleneimine - PEI) which may prevent AuNPs from being oxidized over time. For preparing the SERS substrate, gold nanoparticles were synthesized in aqueous solution of a surfactant, cetyltrimethyl ammonium bromide (CTAB), via a seed mediated process. Before embedding in PEI, aqueous gold nanoparticles were centrifuged to remove excess CTAB and drop casted the films. Amount of gold nanoparticles be imbedded in the polymer was optimized and the SERS films were fabricated in the presence and absence of the cross-linker, adipic acid. The reproducibility of the AuNP size, shape, and particle distribution was confirmed by TEM measurements. The surface plasmon resonance (SPR) of aqueous gold nanoparticles was evaluated by UV-Visible spectroscopy. Raman spectra were collected from aqueous drops of thiosalicylic acid (TSA) on the PEI-AuNP film at the optimum pH of 7.0. The limit of detection for TSA on our SERS films was determined to be 10-7 M. Initial long-term studies of SERS signal for TSA on the fabricated PEI-AuNP templates showed degradation within 3 weeks. The data suggests that alternative cross-linkers may provide better stability and homogeneity of the SERS signal.

#38 Investigating the Potential of Silver Hydroxyapatite as an Implant Coating for Preventing Prosthetic Joint

Infection

Luke S. DeHart, Austin Dinkins, Dr. Mary Tecklenburg Department of Chemistry and Biochemistry, Central Michigan University, Mt. Pleasant, Michigan Substantial progress in medicine has dramatically increased life expectancy in developed countries. Alongside this increase in life expectancy there has also been a drastic increase in the number of people who suffer from degenerative joint disease, the ultimate treatment for this disease is a total joint arthroplasty. In the United States alone it is estimated that by 2020 the number of patients who will need to undergo a total knee arthroplasty will rise to 3.48 million per year, a 678% increase from 2005. It is estimated that one to two percent of these patients will develop a prosthetic joint infection (PJI) at some point after their treatment. Prosthetic joint infections are associated with a fivefold increase in mortality rate and a significant economic impact with number estimates ranging between 560 million to over one billion dollars annually. Recent advances in nanoparticle synthesis have enabled comparing the effectiveness of silver ions versus silver nanoparticles as an antimicrobial agent. Silver ions, individual charged atoms, will replace calcium ions in the hydroxyapatite. Silver nanoparticles, clusters of thousands of atoms, will be mixed into the hydroxyapatite. Investigating the antimicrobial properties of both of these silver types in hydroxyapatite will give insight into novel methods to prevent the development of biofilms on prosthetic implants. Utilizing silver integrated hydroxyapatite as a biocompatible and biodegradable surface coating for prosthetic implants could prevent biofilm formation and the development of a prosthetic joint infection without the use of antibiotics. Three forms of hydroxyapatite were synthesized, pure hydroxyapatite, silver ion doped hydroxyapatite and silver nanoparticle infused hydroxyapatite. The antimicrobial properties and prevention of biofilm formation for each of the different types of hydroxyapatite pellets will be tested.

#39 STEM Outreach from Midland ACS--A Variety of Approaches for Diverse Audiences

Regina Malczewski, Michelle Rivard Midland ACS

Midland ACS Outreach has evolved over the past 30 years, always trying to meet the needs of our audiences, while offering programs that are creative, relevant, and FUN, and meeting educational and social needs. In the past year, we have used grants from Midland, Bay and Saginaw Community Foundations, as well as donations, to fund teacher workshops in rural Guatemala, district-wide classroom chemistry experiences for Bay City eighth graders, specialized hands-on experiences for honor students, training for librarians to conduct STEM programs, and various walk-by or community interactive opportunities in Saginaw and Midland. As members of the Great Lakes Bay STEM Alliance’s Out of School Time Network, we are expanding on-traditional programs that show participants that chemistry truly is EVERYWHERE. From our community garden to our food science cafes and multi-day programs with Society for Women Engineers, Delta Possible Dream and St. Brigid School, our programs have been designed to meet the needs of our hosts and target audiences. This poster will describe our specific efforts in various communities, the volunteer hours spent, the collaborations we have established, and our measures of success. One of the latter is the recognition received from National ACS, including various awards for "Outstanding Kids and Chemistry", international and sustainability efforts, and for Earth Day and National Chemistry Week programming.

#40 An "Explosion" of Learning: Experiences at Midland High School with Lessons on Pop and Mentos Regina Malczewski, Dave Stickles, Michelle Rivard, Anne Kelly-Rowley Midland ACS Outreach

The Diet Coke and Mentos reaction is culturally well-known, and presents many opportunities for the practice of chemistry. During several years of experience with a Pop and Mentos lesson engaging Midland High School Chemistry 1 (or higher level) students, Midland ACS Outreach has been able to use this phenomenon to teach physical reactions, execution of the scientific method, simple lab skills, and the impacts of several variables on the interaction itself. Students witnessed an example reaction (all experiments were done in a room with high ceilings, and inside a kiddie pool surrounded by a tarp) and then sent to stations where each group focused on specific reaction conditions. Supplies were provided (including geyser tubes and12 or 16.9 -oz bottles of soda, depending on the experimental parameter being evaluated), along with reference data and worksheets for team development of hypotheses and conclusions. The demonstrated procedure allowed quantification of the reaction by measuring post-explosion liquid volume; all student groups were required to document hypotheses and articulate step-by-step methods for their experiment in order to get approval to run their reactions. Using this strategy, the effects of parameters such as temperature, pop age, geyser tube type, Mentos type, sweetener, caffeine level and brand of soda were investigated. Classroom findings will be presented for each of these, along with learnings regarding student abilities and sources of error. The temperature and age of the soda were found to have the most significant impacts on the reaction; the investigation of surface area effects also showed interesting results.