electrical, optical, and magnetic properties of organic...

Electrical, Optical, and Magnetic Propertiesof Organic Solid State Materials

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Cambridge University Press978-1-107-40976-7 - Electrical, Optical, and Magnetic Properties of Organic Solid State MaterialsMaterials Research Society Symposium Proceedings: Volume 247Editors: Long Y. Chiang, Anthony F. Garito and Daniel J. Sandman FrontmatterMore information

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MATERIALS RESEARCH SOCIETY SYMPOSIUM PROCEEDINGS VOLUME 247

Electrical, Optical, and Magnetic Propertiesof Organic Solid State Materials

Symposium held December 2-6, 1991, Boston, Massachusetts, U.S.A.

EDITORS:

Long Y. ChiangExxon Research and Engineering Company, Annandale, New Jersey, U.S.A.

Anthony F. GaritoUniversity of Pennsylvania, Philadelphia, Pennsylvania, U.S.A.

Daniel J. SandmanGTE Laboratories Incorporated, Waltham, Massachusetts, U.S.A.

IMTRISI MATERIALS RESEARCH SOCIETYPittsburgh, Pennsylvania






cambridge university press Cambridge, New York, Melbourne, Madrid, Cape Town, Singapore, São Paulo, Delhi, Mexico City

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© Materials Research Society 1992

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This work was supported by the Air Force Office of Scientific Research, Air ForceSystems Command, USAF, under Grant Number AFOSR 91-0344.






Contents

PREFACE xv

MATERIALS RESEARCH SOCIETY SYMPOSIUM PROCEEDINGS xviii

PART I: NONLINEAR OPTICAL ORGANICS

EXCITED STATE ENHANCEMENT MECHANISM FOR NONRESONANTNONLINEAR OPTICAL PROCESSES 3

J.R. Heflin, Q.L. Zhou, D.C. Rodenberger, Y.M. Cai, and A.F. Garito

•MATERIALS REQUIREMENTS FOR ELECTRO-OPTIC POLYMERS(FOR ELECTRONIC SYSTEMS APPLICATIONS) 17

Rick Lytel and George F. Lipscomb

•QUADRATIC NONLINEAR OPTICAL PROPERTIES OF POLYMERICORGANIC MATERIALS 27

L.-T. Cheng, R.P. Foss, G.R. Meredith, W. Tarn, and F.C. Zumsteg

SYNTHESIS AND NONLINEAR OPTICAL CHARACTERISTICSOF CHROMOPHORE-FUNCTIONALIZED POLYMERS HAVINGCHROMOPHORE-CENTERED HYDROGEN-BONDING AND CROSSLINKINGGROUPS 39

Y. Jin, S.H. Carr, T.J. Marks, W. Lin, and G.K. Wong

CHARACTERIZATION OF GLASSY STATE RELAXATIONS IN STYRENEAND METHACRYLATE BASED NONLINEAR OPTICAL MATERIALS 43

Michael A. Schen and Fred I. Mopsik

POLED POLYIMIDES FOR THERMALLY STABLE ELECTRO-OPTICMATERIALS 49

J.W. Wu, J.F. Valley, M. Stiller, S. Ermer, E.S. Binkley, J.T. Kenney,G.F. Lipscomb, and R. Lytel

HETEROAROMATICS: EXCEPTIONAL MATERIALS FOR SECOND ORDERNONLINEAR OPTICAL APPLICATIONS 59

Alex K-Y. Jen, K.Y. Wong, V. Pushkara Rao, K. Drost, and R.M. Mininni

•TOWARDS ORIENTED POLYMERIC STRUCTURES FOR CUBIC NONLINEAROPTICS 65

J. Le Moigne, M. Moroni, H. Coles, A. Thierry, and F. Kajzar

A THREE-LEVEL MODEL USEFUL FOR EXPLORING STRUCTURE/PROPERTY RELATIONSHIPS FOR MOLECULAR THIRD ORDEROPTICAL POLARIZABILITIES 73

C.W. Dirk, L-T. Cheng, and M.G. Kuzyk

•MULTIPHOTON SPECTRA OF CONJUGATED POLYMERS 79Z.G. Soos, S. Etemad, and R.G. Kepler

INTERMOLECULAR EFFECTS ON THIRD ORDER NONLINEAR OPTICALPROPERTIES 93

D.S. Dudis, A.T. Yeates, and H.A. Kurtz

•Invited Paper






LARGE NONLINEAR REFRACTIVE INDICES OF NICKEL DITHIOLENEDOPED POLYMETHYLMETHACRYLATE 99

Christopher S. Winter, S.N. Oliver, and C.A.S. Hill

ENHANCED THIRD ORDER NONLINEARITY IN MACROCYCLICCOMPOUNDS 105

Masahiro Hosoda, Tatsuo Wada, Anthony F. Garito, and Hiroyuki Sasabe

UV-CURABLE EPOXY BASED SECOND ORDER NONLINEAR OPTICALMATERIAL 111

Ru Jong Jeng, Yong Ming Chen, Braja K. Mandal, Jayant Kumar, andSukant K. Tripathy

SYNTHESIS AND OPTICAL CHARACTERIZATION OF NEW NLO-ACTIVEPOLYURETHANES AND A SILVER COLLOIDAL SUSPENSION IN A SELECTPOLYURETHANE 117

P. Kitipichai, R. LaPeruta, Jr., G.M. Korenowski, G.E. Wnek, andI. Gorodisher

LATTICE BENDING IN POLY(DIACETYLENE) DROPLETS NEAR SURFACES 123Patricia M. Wilson and David C. Martin

POLY(VINYL ETHERS) AS NONLINEAR OPTICAL MATERIALS, SHG INCORONA POLED POLYMER FILMS 129

Gert S'Heeren, Guy Vanermen, Celeste Samyn, Marcel Van Beylen, andAndre Persoons

NONLINEAR OPTICAL MATERIAL FABRICATION VIA SOL-GEL PROCESSING 135Jongsung Kim and Joel L. Plawsky

*ALL-OPTICAL SWITCHES AND ALL-OPTICAL BISTABILITY BY NONLINEAROPTICAL MATERIALS 141

K. Sasaki, S. Sasaki, and O. Furukawa

*NONLINEAR OPTICS OF LINEAR CONJUGATED POLYMERS 151D. Guo, S. Mazumdar, G.I. Stegeman, M. Cha, D. Neher, S. Aramaki,W. Torruellas, and R. Zanoni

THE NONLINEAR OPTICAL PROPERTIES OF POLYACETYLENE WITHINTHE INTERMEDIATE EXCITON FORMALISM 163

David Yaron and Robert Silbey

EXACT OPTICAL SUSCEPTIBILITIES OF THREE STATE SYSTEMSINTERACTING WITH A SINGLE FREQUENCY ELECTRIC FIELD 169

Theresa C. Kavanaugh and Robert J. Silbey

DAMPING AND THIRD-ORDER NONLINEAR SPECTRUM OFPOLYACETYLENE 175

Xin Sun, Rong-Tang Fu, Lie-Ming Li, D.L. Lin, and Thomas F. George

"LINEAR AND NONLINEAR OPTICAL PROPERTIES OF PROCESSABLEPOLYMERIC MATERIALS 179

Toshikuni Kaino, Satoru Tomaru, Takashi Kurihara, and Michiyuki Amano

SYNTHESIS, CHARACTERIZATION, AND PROCESSING OF ORGANIC NLOPOLYMERS 191

Mark A. Druy, Paul J. Glatkowski, and Ryszard Burzynski

THIRD-ORDER NONLINEAR OPTICAL PROPERTIES OF PHTHALOCYANINES 197James S. Shirk, J.R. Lindle, Steven R. Flom, F.J. Bartoli, andArthur W. Snow

•Invited Paper

vi






THIRD ORDER NONLINEAR OPTICAL RESPONSES OFMETALLOPHTHALOCYANINES IN FILMS AND SOLUTIONS 203

Roger J. Reeves, Richard C. Powell, Warren T. Ford, Young H. Chang,and Weiming Zhu

THE DOMAIN MODE IN FERROELECTRIC LIQUID CRYSTALS: A NOVELELECTROOPTICAL PROCESS 209

L.A. Beresnev, M. Pfeiffer, S.A. Pikin, and W. Haase

PHOTOCONDUCTIVITY IN AN EPOXY-BASED PHOTOCROSSLINKABLENONLINEAR OPTICAL POLYMER 217

Lian Li, R.J. Jeng, J.Y. Lee, Y. Yang, J. Kumar, and S.K. Tripathy

DIELECTRIC STUDY OF A PHOTOCROSSLINKABLE NONLINEAROPTICAL POLYMER 223

J.I. Chen, R.A. Moody, Y.M. Chen, J.Y. Lee, S.K. Sengupta, J. Kumar,and S.K. Tripathy

DYNAMIC MECHANICAL BEHAVIOR OF PHOTOCROSSLINKABLENONLINEAR OPTICAL POLYMERS 229

S. Marturunkakul, J.Y. Lee, S.K. Sengupta, J. Kumar, and S.K. Tripathy

EPITAXIAL GROWTH OF ORGANIC NONLINEAR OPTICAL MATERIALS 235Y. Hattori, A. Mizoguchi, Y. Ogaki, and A. Nishimura

ELECTRICAL AND OPTICAL PROPERTIES OF THERMID POLYIMIDE 241Patrick G. Jobe, Christine Puglisi, Z.X. Zhu, K.J. Fang, D. Liu, N. Patel,E. Niver, H. Grebel, G.M. Qin, K.D. Moller, S.N. Zhao, G. Feng,N.M. Ravindra, and K.K. Chin

CUBIC NONLINEAR OPTICAL PROPERTIES OF THIN FILMS OF A SERIESOF AROMATIC SCHIFF BASE POLYMERS 247

Chen-Jen Yang, Samson A. Jenekhe, Herman Vanherzeele, andJeffrey S. Meth

THIRD-ORDER NONLINEAR OPTICAL PROPERTIES OF A SERIESOF SYSTEMATICALLY DESIGNED CONJUGATED RIGID-RODPOLYQUINOLINES 253

Ashwini K. Agrawal, Samson A. Jenekhe, Herman Vanherzeele,and Jeffrey S. Meth

BENZTHIAZOLE AND THIOPHENE CAPPED POLYENES FOR NONLINEAROPTICAL APPLICATIONS: SINGLE CRYSTAL, SEMI-EMPIRICAL ANDAB INITIO RESULTS 259

A.T. Yeates, D.S. Dudis, T. Resch, and A.V. Fratini

A NEW ORGANIC CRYSTAL-MHBA FOR POTENTIAL DIODE LASERSECOND-HARMONIC GENERATION 265

Minhua Jiang, Xutang Tao, Duorong Yuan, Nan Zhang, and Zongshu Shao

MECHANISMS OF THE NONLINEAR OPTICAL RESPONSE INTETRAKIS(CUMYLPHENOXY)PHTHALOCYANINES 271

Steven R. Flom, James S. Shirk, J.R. Lindle, F.J. Bartoli, Zakya H. Kafafi,R.G.S. Pong, and Arthur W. Snow

THIRD- AND FIFTH-ORDER OPTICAL PROPERTIES OF TRANSITIONMETAL COMPLEXES OF BENZENEDITHIOL AT 1.064 /*m 277

J.R. Lindle, C.S. Weisbecker, F.J. Bartoli, R.G.S. Pong, and Z.H. Kafafi

•Invited Paper

VII






PART II: CHEMICAL MODIFICATIONS OF FULLERENES

SYNTHESIS OF FULLEROLS AS POLYHYDROXYLATED FULLERENEDERIVATIVES 285

Long Y. Chiang, Ravi Upasani, John W. Swirczewski, and Kathy Creegan

FUNCTIONALIZING C60 VIA NUCLEOPHILIC TRAPPING OF ITS RADICALCATIONS: 1. ALKOXYLATION AND ARYLATION OF C60; 2. SYNTHESISOF EARMUFF ETHERS (DIFULLEROXYALKANES) 293

Glen P. Miller, Chang S. Hsu, Hans Thomann, Long Y. Chiang, andMarcelino Bernardo

FUNCTIONALIZING FULLERENES THROUGH CYCLOADDITIONREACTIONS 301

Ripudaman Malhotra, Subhash C. Narang, Asutosh Nigam,S. Ganapathiappan, Susanna Ventura, Apparao Satyam, Tilak Bhardawaj,and Donald C. Lorents

C60 WITH METALLOPORPHYRINS 307Alain Penicaud, John Hsu, and Christopher Reed

SUPERCONDUCTIVE PROPERTIES OF CsxRbvC60 (33K) - ISOTOPE EFFECT 311T.W. Ebbesen, K. Tanigaki, S. Saito, J. Mizuki, J.S. Tsai, Y. Kubo,and S. Kuroshima

PHYSICAL PROPERTIES OF SUPERCONDUCTING AND FERROMAGNETICMATERIALS BASED ON C60 315

J.D. Thompson, G. Sparn, F. Diederich, G. Griiner, K. Holczer, R.B. Kaner,R.L. Whetten, P.-M. Allemand, Q. Li, and F. Wudl

STRUCTURES AND PROPERTIES OF C60 & C70 THIN FILMSFABRICATED BY ORGANIC MBE 321

K. Tanigaki, T. Ichihashi, T.W. Ebbesen, S. Kuroshima, S. Iijima,H. Hiura, and H. Takahashi

DEFECTIVE BUCKYBALLS: ALTERNATIVE STRUCTURAL ISOMERS OF C60 327Krishnan Raghavachari and Celeste M. Rohlfmg

ELECTRONIC STRUCTURE OF CARBON FIBERS BASED ON C60 333Riichiro Saito, Mitsutaka Fujita, G. Dresselhaus, and M.S. Dresselhaus

ELECTRONIC STRUCTURE OF FULLERENE TUBULES 339J.W. Mintmire, D.H. Robertson, B.I. Dunlap, R.C. Mowrey, D.W. Brenner,and C.T. White

ESR STUDIES OF THE ANION RADICALS OF THE FULLERENE: C60n"

(n= l , 2, AND 3) 345Dominique Dubois, M. Thomas Jones, and Karl M. Kadish

PHOTOELECTRON SPECTRA OF C , ^ AND C60H6p 351B.I. Dunlap, J.W. Mintmire, D.H. Robertson, D.W. Brenner, R.C. Mowrey,and C.T. White

SYNTHESIS OF A C60-PARA-XYLYLENE COPOLYMER 355Douglas A. Loy and Roger A. Assink

NONLINEAR OPTICAL PROPERTIES OF BUCKMINSTERFULLERENESOLUTIONS 361

Donna Brandelik, Daniel McLean, Mark Schmitt, Bob Epling,Chris Colclasure, Vince Tondiglia, Ruth Pachter, Keith Obermeier, andRobert L. Crane

viii






OPTICAL PROPERTIES OF C60 AND M6C60 (M=K,Rb,Cs) FILMS 367S.L. Ren, Ying Wang, M. Holden, A.M. Rao, H.F. Ni, W. Lee,G.T. Hager, and P.C. Eklund

RAMAN SCATTERING IN MxQn FILMS (M=K,Rb,Cs; x=0,3,6) 373Kai-An Wang, Ping Zhou, Ying Wang, J.M. Holden, Song-lin Ren,G.T. Hager, H.F. Ni, P.C. Eklund, G. Dresselhaus, and M.S. Dresselhaus

ELECTRONIC EFFECTS OF ADDUCTS ON C60: A MOLECULAR ORBITALANALYSIS 379

Y.C. Fann, D. Singh, and S.A. Jansen

INTERESTING ELECTRONIC PROPERTIES GENERATED BY METAL-IONLINKED C6Q CHAINS 385

D.J. Singh, Y.C. Fann, and S.A. Jansen

NONLINEAR OPTICAL PROPERTIES OF BUCKMINSTERFULLERENE, C60,IN THE NEAR-INFRARED 393

Z.H. Kafafi, J.R. Lindle, R.G.S. Pong, F.J. Bartoli, L.J. Lingg, andJ. Milliken

IN SITU PHOTOCONDUCTIVE STUDY OF C60 AND PHTHALOCYANINETHIN FILMS 399

Nobutsugu Minami

PART III: ORGANIC FERROMAGNETICAND RELATED MATERIALS

•APPROACHES FROM HIGH-SPIN ORGANIC MOLECULES TO ORGANICFERROMAGNETS 407

Takayuki Ishida, Katsuya Inoue, Noboru Koga, Nobuo Nakamura, andHiizu Iwamura

•MAGNETIC PROPERTIES IN CHARGE-TRANSFER COMPLEXES OF HIGH-SYMMETRY pRGANIC ACCEPTORS 417

Toyonari Sugimoto, Eiji Murahashi, Kaoru Ikeda, Zen-Ichi Yoshida,Hiroshi Nakatsuji, Jun Yamauchi, Yasushi Kai, and Nobutami Kasai

FINDING OF BULK FERROMAGNETISM IN STABLE ORGANIC RADICALCRYSTAL 429

Minoru Kinoshita

SYNTHESIS OF NEW STABLE FUNCTIONALIZED ORGANIC RADICALSFOR THE STUDY OF THEIR MAGNETIC PROPERTIES 435

Long Y. Chiang, Ravi B. Upasani, and John W. Swirczewski

SYNTHESIS AND MAGNETIC CHARACTERIZATION OF POLY(2,4-BIS(4,4,5,5-TETRAMETHYL-4,5-DIHYDRO-lH-IMIDAZOLYL-l-OXY-3-OXIDE-2-PHENOXY))HEXADIIYNE 443

Deqing Zhang, Peigi Wu, Daoben Zhu, and Wensheng Zhou

INTERELECTRONIC EXCHANGE INTERACTIONS BETWEEN ORGANICRADICALS IN THE SOLID STATE 449

Frank C. Rossitto and Paul M. Lahti

•METALLOMESOGENS AND AMORPHOUS METALLOPOLYMERS:MAGNETIC PROPERTIES 455

W. Haase, K. Griesar, and C. Erasmus-Buhr

•Invited Paper






FERRO- AND ANTIFERROMAGNETIC BEHAVIORS OF SOMEORGANOMETALLIC AND COORDINATED COMPOUNDS 463

H.H. Wei and Y.F. Chang

PART IV: MOLECULAR ORGANIC CONDUCTORS

•SYNTHESES AND PROPERTIES OF K-PHASE ORGANICSUPERCONDUCTORS 471

H. Hau Wang, K.D. Carlson, U. Geiser, A.M. Kini, A.J. Schultz,J.M. Williams, U. Welp, K.E. Darula, V.M. Hitsman, M.W. Lathrop,L.A. Megna, P.R. Mobley, G.A. Yaconi, J.E. Schirber, and D.L. Overmyer

*DESIGN OF ORGANIC SUPERCONDUCTORS BASED ON BEDT-TTF 483Gunzi Saito, Tokutaro Komatsu, Toshikazu Nakamura, and Hideki Yamochi

SUPERCONDUCTING TRANSITION IN K-BEDT-TTF SALTS UNDERMAGNETIC FIELD 495

Hiroshi Ito, Yoshio Nogami, Masashi Watanabe, Takehiko Ishiguro,Tokutaro Komatsu, Gunzi Saito, and Nobuyoshi Hosoito

STUDY OF THE SOLID STATE PROPERTIES OF AN ORGANICSUPERCONDUCTOR 501

Raul Fainchtein, S.T. D'Arcangelis, S.S. Yang, and D.O. Cowan

CATION RADICAL SALTS OF S,S-DMBEDT-TTF: SEMICONDUCTORS,METALS AND A NEW ORGANIC SUPERCONDUCTOR 509

John S. Zambounis, Carl W. Mayer, Kurt Hauenstein, Bruno Hilti,Walther Hofherr, Jurgen Pfeiffer, Markus Biirkle, and Grety Rihs

FERMI SURFACE STUDY OF ORGANIC METALS (BEDT-TTF^X 515M. Tokumoto, A.G. Swanson, J.S. Brooks, C.C. Agosta, S.T. Hannahs,N. Kinoshita, H. Anzai, M. Tamura, H. Tajima, H. Kuroda, A. Ugawa,and K. Yakushi

TETRAHETERAFULVALENES AS PRECURSORS OF CONDUCTINGMATERIALS 523

George C. Papavassiliou

THE SYNTHESIS AND PHYSICAL STUDIES OF A NEW SYNTHETIC METAL:THE CHARGE-TRANSFER SALT OF DIMETHYLTETRATHIOTETRACENE-TETRACYANOETHYLENE 529

K.J. Kilgore, N.P. Rath, and M.T. Jones

CONDUCTING AND SUPERCONDUCTING SALTS BASED ON SOMESYMMETRICAL AND UNSYMMETRICAL DONORS 535

George C. Papavassiliou, D.J. Lagouvardos, V.C. Kakoussis, A. Terzis,A. Hountas, B. Hilti, C. Mayer, J.S. Zambounis, J. Pfeiffer,M.-H. Whangbo, J. Ren, and D.B. Kang

SYNTHESIS OF A NOVEL DONOR, BTFE-DMB, AND ELECTRICALPROPERTIES OF ITS IODINE SALT 541

Makoto Mizutani, Keiji Tanaka, Kiyoshi Ikeda, and Kazushige Kawabata

SYNTHESIS AND PHYSICAL PROPERTIES OF TWO ORGANIC DONORDERIVATIVES OF 12-MOLYBDOPHOSPHATE ANION (PMo^OJ11': NEWEXAMPLES OF MIXED-VALENCE ORGANIC DONOR-INORGANICACCEPTOR COMPOUNDS 545

D. Attanasio, C. Bellitto, M. Bonamico, G. Righini, and G. Staulo

CHEMICAL PROPERTIES OF PORPHYRIN THIN FILMS DEPOSITED BY ICB 551Hiroaki Usui, Atsushi Yamada, Kouji Murayama, and Isao Yamada

•Invited Paper






STUDIES ON THE CHEMICAL MODIFICATIONS OF METALLO-ORGANICCHARGE-TRANSFER COMPLEX SWITCHING AND MEMORY STORAGEMATERIALS 557

Hailing Duan, Dwaine O. Cowan, and Theodore O. Poehler

PART V: ORGANIC CONJUGATED POLYMERS

*POLYANILINE: INTERRELATIONSHIPS BETWEEN MOLECULAR WEIGHT,MORPHOLOGY, DONNAN POTENTIAL, AND CONDUCTIVITY 565

Alan G. MacDiarmid and Arthur J. Epstein

ENERGY BAND STRUCTURE FOR METALLIC POLYACETYLENE 577Chizuko Tanaka and Jiro Tanaka

SUPERPOLARON MODEL OF METALLIC POLYACETYLENE 583A. Takahashi, S. Yamamoto, and H. Fukutome

•STRUCTURAL ASPECTS OF THE POLYANILINE FAMILY OF ELECTRONICPOLYMERS 589

J.P. Pouget, M. Laridjani, M.E. Jozefowicz, A.J. Epstein, E.M. Scherr,and A.G. MacDiarmid

NOVEL TEMPLATE GUIDED SYNTHESIS OF POLYANILINE 601Jia-Ming Liu, Linfeng Sun, Jyun-Hwei Hwang, and Sze Cheng Yang

DIETHER SUBSTITUTED POLY ANILINES: NOVEL ELECTRODEMATERIALS 607

J. Gopal, K. Vanhouten, D.O. Cowan, T.O. Poehler, P.V. Madsen, andP.C. Searson

DYNAMICS OF ELECTROCHROMIC PHENOMENA IN ORGANICCONDUCTING POLYPYRROLE FILMS 613

T. Amemiya, K. Hashimoto, and A. Fujishima

SYNTHESIS OF HETEROCYCLIC MONOMERS DESIGNED TO PRODUCECONDUCTING POLYMERS WITH SPECIFIC REDOX REQUISITES AND TOEVALUATE STEREOCHEMICAL FACTORS INFLUENCING THECONDUCTIVITY 619

Anna Berlin, Elisabetta Brenna, Giorgic A. Pagani, Franco Sannicolo,Gianni Zotti, and Gilberto Schiavon

THE POLYMERIZATION OF HETEROCYCLES ON CLAY TEMPLATES 625Loic Mane, Pierre Laszlo, and Jean-Claude Dubois

AN OVERVIEW OF CONJUGATED POLYMERS IN THEIR INSULATINGFORMS 631

Daniel J. Sandman

*POLYARENEMETHYLIDENES, A NEW CLASS OF LOW GAP POLYMERS 637M. Hanack, G. Hieber, K.-M. Mangold, H. Ritter, and U. Rohrig

LIGHT-EMITTING DIODES BASED ON CONJUGATED POLYMERS:CONTROL OF COLOUR AND EFFICIENCY 647

Paul L. Burn, A.B. Holmes, A. Kraft, A.R. Brown, D.D.C. Bradley, andR.H. Friend

CHARGE CARRIER GENERATION BY EXCITON-EXCITON ANNIHILATIONIN POLY(DI-N-HEXYLSILANE) 655

R.G. Kepler and Z.G. Soos

•Invited Paper






RECENT STUDIES OF RAMAN SPECTROSCOPY OF POLYDIACETYLENECRYSTALS: POLY-IPUDO 661

S.H.W. Hankin and D.J. Sandman

PHOTOINDUCED ABSORPTION SPECTROSCOPY OF POLY-3-ALKYLTHIOPHENES 669

C. Botta, S. Luzzati, A. Bolognesi, R. Tubino, and A. Borghesi

OPTICAL SPECTROSCOPY AND PHOTOCHEMISTRY OF THIN FILMS OFPROPYLMETHYLPOLYAZINE 675

Bradford C. Sherman and William B. Euler

SYNTHESIS AND CHARACTERIZATION OF SOLUBLE ALKYLSUBSTITUTED POLY(2,5-THIENYLENE VINYLENES) 681

M. Catellani, W. Porzio, A. Musco, and R. Pontellini

HIGHLY CONDUCTING AND THERMALLY STABLE CONJUGATEDPOLYMERS 687

Alex K-Y. Jen, Michael Drzewinski, Hui Hwui Chin, and Guilio Boara

IN-SITU MONITORING OF THE KINETICS AND MECHANISM OFCONDUCTING POLYMER SYNTHESIS 693

Yoke Fong, Chengbo Chen, and Joseph B. Schlenoff

ELECTRICALLY CONDUCTIVE COMPOSITE OF POLYPYRROLE ANDLIQUID CRYSTALLINE AROMATIC COPOLYAMIDE 699

Jing-Sheng Bao, C.C. Xu, W. Cai, and Xian-Tong Bi

SYNTHESIS AND MICROWAVE CHARACTERIZATION OF POLYPYRROLE-PVC BLENDS 705

F. Jousse, P. Hourquebie, C. Deleuze, and L. Olmedo

STRUCTURE AND MORPHOLOGY OF METALLIC-CONDUCTIVEPOLYACETYLENE 711

Jun Tsukamoto and Akio Takahashi

CHEMICAL AND ELECTROCHEMICAL DOPING OF PPS IN SULFURICACID 717

C. Arbizzani, M. Mastragostino, G. Dellepiane, and P. Piaggio

DEFECTS IN [l,6-DI(N-CARBAZOLYL)-2,4-HEXADIYNE] DIACETYLENECRYSTALS 723

Jun Liao and David C. Martin

POLARIZATION DEPENDENT PHOTOCURRENT IN THIN FILMPOLYDIACTYLENE SINGLE CRYSTALS 729

Y. Yang, J.Y. Lee, L. Li, J. Kumar, A.K. Jain, S.K. Tripathy,H. Matsuda, S. Okada, and H. Nakanishi

ION IMPLANTATION OF CONDUCTING LADDER AND RIGID-RODPOLYMERS 735

A. Burns, Z.H. Wang, G. Du, J. Joo, A.J. Epstein, J.A. Osaheni,S.A. Jenekhe, and C.S. Wang

THE 1.5 eV POLARON TRANSITION OF POLYANILINE: THE SPECTRAELECTROCHEMICAL RESOLUTION INTO SUB-BANDS 741

Hong Liao and Sze Cheng Yang

MECHANICAL AND ELECTRICAL PROPERTIES OF HEAT-TREATEDLADDER POLYMER FIBER 747

C.S. Wang, C. Y-C Lee, and F.E. Arnold

XII






EFFECTS OF HUMIDITY AND HEAT ON THE CONDUCTIVITY OFPOLY(3-ALKYLTHIOPHENES) 753

E. Punkka, H. Isotalo, M. Ahlskog, and H. Stubb

FABRICATION OF AN ELECTRICALLY CONDUCTING FULL-INTERPENETRATING POLYMER NETWORK 759

Yading Wang and M.F. Rubner

PART VI: MOLECULAR ENGINEERING OF ORGANIC MATERIALS

•MOLECULAR ENGINEERING OF POLYMERS AND POLYMER SYSTEMSFOR PHOTONICS AND ELECTRONICS 767

Gerhard Wegner and Klemens Mathauer

LAYER-BY-LAYER MOLECULAR ASSEMBLY APPROACHES TO THECONSTRUCTION OF THIN FILMS HAVING HIGH SECOND-ORDEROPTICAL NONLINEARITIES 779

David S. Allan, Fuyuhiko Kubota, Ashok K. Kakkar, Tobin J. Marks,Tongguang Zhang, Weiping Lin, Mingchih Shin, George K. Wong,and Pulak Dutta

A TWO-LEGGED SPACER MOLECULAR FOR ALTERNATE LAYER LBFILM DEPOSITION WITH OPTICALLY NONLINEAR DYES 787

G.J. Ashwell, W.A. Crossland, P.J. Martin, P.A. Thompson,A.T. Hewson, and S.D. Marsden

THIN FILM CRYSTALLINE ORGANIC SEMICONDUCTORS: A NEWCLASS OF ENGINEERED MATERIALS FOR OPTOELECTRONICS 793

E.I. Haskal, F.F. So, D.Y. Zang, and S.R. Forrest

•NANOSCOPIC MOLECULAR ENGINEERING: ORGANIC MBE AND STM 805Masahiko Hara, Anthony F. Garito, and Hiroyuki Sasabe

*GRADED-INDEX AND SINGLE-MODE POLYMER OPTICAL FIBERS 817Yasuhiro Koike

QUANTUM WELL FORMATION IN ONE-DIMENSIONAL POLYMER FILMSBY MOLECULAR LAYER DEPOSITION AND CHEMICAL VAPORDEPOSITION 829

Tetsuzo Yoshimura, Satoshi Tatsuura, and Wataru Sotoyama

UNUSUAL X-RAY DIFFRACTION VECTOR SHIFT OBSERVED INHETEROGENEOUS LANGMUIR-BLODGETT MULTILAYER FILMS 835

Yoshio Nogami, Kazuyoshi Ogasawara, Shigeki Takeuchi,Takehiko Ishiguro, Kazumasa Ohsumi, and Yutaka Shimizugawa

MECHANISMS OF PHOTO CURRENTS IN PHTHALOCYANINE THIN FILMSOLAR CELLS 841

Susanne Siebentritt, Stefan Giinster, and Dieter Meissner

PLASMA ACTIVATED CHEMICAL VAPOR DEPOSITION OFPOLYTHIOPHENE THIN FILMS 847

J.D. Targove, P.D. Haaland, and C.A. Kutsche

NOVEL LANGMUIR-BLODGETT FILMS OF ELECTRICALLY CONDUCTINGPOLYION COMPLEXES AND DIBLOCK COPOLYMERS 853

A. Timothy Royappa, Randall S. Saunders, Robert E. Cohen,and Michael F. Rubner

•Invited Paper

xi i i






NEW STRATEGIES FOR PREPARING ELECTRICALLY CONDUCTIVELANGMUIR-BLODGETT FILMS 859

J.H. Cheung, R.B. Rosner, and M.F. Rubner

APPLICATION OF POSITRON ANNIHILATION METHODS FORINVESTIGATION AND TESTING OF POLYMER 865

S.A. Tishin, V.A. Tishin, and V.N. Kestelman

HIGH RESOLUTION ORGANIC THIN FILM MAPPING FOR PROCESSCONTROL 871

David Denenberg and Austin R. Blew

DEFECT STUDIES OF THE TRANSPARENT/TRANSLUCENT PLASTICPRODUCTS WITH THE POLARIZED LIGHT 877

Miftahur Rahman and N.R. Schott

INVESTIGATION OF POLYMER RELAXATION AFTER DEFORMATIONBY POSITRON ANNIHILATION 883

Sergey A. Tishin, Mihail I. Tsapovestsky, Vladimir A. Tishin, andVladimir N. Kestelman

DEVELOPMENT OF A COMPUTER PROGRAM FOR THE DETERMINATIONOF OPTICAL CONSTANTS OF RADIATION DAMAGED OPTICALELEMENTS USING CLASSICAL OSCILLATOR FIT TO REFLECTANCEAND/OR TRANSMITTANCE DATA 889

Miftahur Rahman, C. Yang, K.S. Chiu, A.S. Karakashian, C. Karp,T. Mooney, and G. Al-Jumaily

AUTHOR INDEX 895

SUBJECT INDEX 899

XIV






Preface

This volume contains the proceedings of the symposium "Electrical, Optical, andMagnetic Properties of Organic Solid State Materials" held in Boston at the Fall Meeting of theMaterials Research Society, December 2-6, 1991. The objective of the symposium was toprovide an interactive forum, multidisciplinary in scope and international in character, fordiscussion of current results in the science and technology of these materials so as to allowassessment of the state-of-the-art of various topics and to point to fruitful directions for furtherprogress. This was the second MRS symposium to address the broad area of the study oforganic molecular and polymeric solids as active electronic, optical, and magnetic elements, andit was initially conceived as a successor to the earlier symposium.1 This activity was deemedappropriate in the face of continuing scientific and technical advances in these materials,especially in the electronic and photonic areas, fueled in large part by significant advances inthe "molecular engineering" of structures for such purposes. As planning proceeded, it becameapparent that results in the new molecular forms of carbon known as fullerenes merited theattention of this symposium, and a special evening session devoted to these materials was addedto the program.

The response to this symposium from the international community interested in thematerials science, chemistry, physics, and engineering of these materials was excellent. Inaddition to the United States, there were contributions from Belgium, Canada, the People'sRepublic of China, Finland, France, Germany, Greece, Israel, Italy, Japan, the Netherlands,Portugal, Switzerland, Taiwan, the United Kingdom, and the former U.S.S.R. The symposiumconsisted of 41 invited talks and approximately 170 contributed presentations. It is not possibleto have a symposium of this magnitude without considerable financial support. Hence, we arepleased to acknowledge the following donors:

Defense Advanced Research Projects AgencyU.S. Air Force Office of Scientific ResearchAllied SignalEastman Kodak CompanyE.I. duPontEnichem AmericaExxon CorporationExxon Corporate Research CenterGE Corporate Research and DevelopmentGTE Laboratories IncorporatedLehighton Electronics, Inc.Lockheed Missiles and Space Company

The program was organized into subject sessions as follows:

1. Plenary2. Second order nonlinear optics3. Third order nonlinear optics4. Organic metals, superconductors, and charge-transfer salts5. Conjugated conducting polymers6. Molecular engineering7. Conjugated polymers in insulating forms8. Organic and polymeric ferromagnets9. Chemical modification and applications of fullerenes

The invited speakers were selected to ensure that the leading programs from academic,industrial, and government laboratories were represented. We are pleased to thank the plenarylecturers, A.F. Garito (U. of Pennsylvania), G. Wegner (Max-Planck-Institute, Mainz), andD.O. Cowan (John Hopkins U.) as well as G. Bjorklund (IBM Almaden), P.M. Chaikin(Princeton U.), L.-T. Cheng (duPont), A.J. Epstein (Ohio State U.), S. Etemad (BellCommunications Research), S.R Forrest (USC), W. Haase (Technische Hochschule,Darmstadt), R.C. Haddon (AT&T Bell Laboratories), C.C. Han (Allied Signal), M. Hanack(U. of Tubingen), M. Hara (RIKEN), A.J. Heeger (U. of California, Santa Barbara), M.Iwamura (U. of Tokyo), T. Kaino (NTT), Y. Koike (Keio U.), M. Lahav (Weizmann Institute),

xv






J. LeMoigne (Inst. of C. Sadron, Strasbourg), R. Lytel (Lockheed), A.G. MacDiarmid (U. ofPennsylvania), S. Mazumdar (U. of Arizona), G. Mohlmann (AKZO), A.A. Ovchinnikov(Institute of Chemical Physics, Moscow), J.P. Pouget (U. of Paris, Orsay), G. Saito (KyotoU.), M. Sasaki (Keio U.)f R. Shen (U. of California, Berkeley), R. Silbey (MIT), K. Singer(Case Western Reserve U.), R. Smalley (Rice U.), Z.G. Soos (Princeton U.), G. Stegeman (U.of Central Florida), T. Sugimoto (Kyoto U.), H.H. Wang (Argonne), R.L. Whetten (UCLA),G.M. Whitesides (Harvard U.), G. Wong (Northwestern U.), and F. Wudl (U. of California,Santa Barbara).

We thank all of the symposium participants for their role in making it a success.We thank the authors for their timely contributions and the manuscript reviewers for theirprompt, conscientious responses. Finally, we thank the officers and staff of the MaterialsResearch Society for their guidance in planning both the symposium and this volume.

Long Y. ChiangAnthony F. GaritoDaniel J. Sandman

January 1992

'"Advanced Organic Solid State Materials," edited by Long Y. Chiang, Paul M. Chaikin,Dwaine O. Cowan, Materials Research Society Symposium Proceedings Volume 173, 1990.

XVI






MATERIALS RESEARCH SOCIETY SYMPOSIUM PROCEEDINGS

Volume 219—Amorphous Silicon Technology—1991, A. Madan,Y. Hamakawa, M. Thompson, P.C. Taylor, P.G. LeComber,1991, ISBN: 1-55899-113-1

Volume 220—Silicon Molecular Beam Epitaxy, 1991, J.C. Bean, E.H.C. Parker,S. Iyer, Y. Shiraki, E. Kasper, K. Wang, 1991, ISBN: 1-55899-114-X

Volume 221—Heteroepitaxy of Dissimilar Materials, R.F.C. Farrow,J.P. Harbison, P.S. Peercy, A. Zangwill, 1991, ISBN: 1-55899-115-8

Volume 222—Atomic Layer Growth and Processing, Y. Aoyagi, P.D. Dapkus,T.F. Kuech, 1991, ISBN: 1-55899-116-6

Volume 223—Low Energy Ion Beam and Plasma Modification of Materials,J.M.E. Harper, K. Miyake, J.R. McNeil, S.M. Gorbatkin, 1991,ISBN: 1-55899-117-4

Volume 224—Rapid Thermal and Integrated Processing, M.L. Green,J.C. Gelpey, J. Wortman, R. Singh, 1991, ISBN: 1-55899-118-2

Volume 225—Materials Reliability Issues in Microelectronics, J.R. Lloyd,P.S Ho, C.T. Sah, F. Yost, 1991, ISBN: 1-55899-119-0

Volume 226—Mechanical Behavior of Materials and Structures inMicroelectronics, E. Suhir, R.C. Cammarata, D.D.L. Chung,1991, ISBN: 1-55899-120-4

Volume 227—High Temperature Polymers for Microelectronics, D.Y. Yoon,D.T. Grubb, I. Mita, 1991, ISBN: 1-55899-121-2

Volume 228—Materials for Optical Information Processing, C. Warde,J. Stamatoff, W. Wang, 1991, ISBN: 1-55899-122-0

Volume 229—Structure/Property Relationships for Metal/Metal Interfaces,A.D Romig, D.E. Fowler, P.D. Bristowe, 1991, ISBN: 1-55899-123-9

Volume 230—Phase Transformation Kinetics in Thin Films, M. Chen,M. Thompson, R. Schwarz, M. Libera, 1991, ISBN: 1-55899-124-7

Volume 231—Magnetic Thin Films, Multilayers and Surfaces, H. Hopster,S.S.P. Parkin, G. Prinz, J.-P. Renard, T. Shinjo, W. Zinn, 1991,ISBN: 1-55899-125-5

Volume 232—Magnetic Materials: Microstructure and Properties, T. Suzuki,Y. Sugita, B.M. Clemens, D.E. Laughlin, K. Ouchi, 1991,ISBN: 1-55899-126-3

Volume 233—Synthesis/Characterization and Novel Applications of MolecularSieve Materials, R.L. Bedard, T. Bein, M.E. Davis, J. Garces,V.A. Maroni, G.D. Stucky, 1991, ISBN: 1-55899-127-1

Volume 234—Modern Perspectives on Thermoelectrics and Related Materials,D.D. Allred, G. Slack, C. Vining, 1991, ISBN: 1-55899-128-X

Volume 235—Phase Formation and Modification by Beam-Solid Interactions,G.S. Was, L.E. Rehn, D. Follstaedt, 1992, ISBN: 1-55899-129-8

Volume 236—Photons and Low Energy Particles in Surface Processing,C Ashby, J.H. Brannon, S. Pang, 1992, ISBN: 1-55899-130-1

Volume 237—Interface Dynamics and Growth, K.S. Liang, M.P. Anderson,R.F. Bruinsma, G. Scoles, 1992, ISBN: 1-55899-131-X

m e 238—Structure and Properties of Interfaces in Materials,W.A.T. Clark, C.L. Briant, U. Dahmen, 1992,ISBN: 1-55899-132-8






MATERIALS RESEARCH SOCIETY SYMPOSIUM PROCEEDINGS

Volume 239—Thin Films: Stresses and Mechanical Properties III, W.D. Nix,].C. Bravman, E. Arzt, L.B. Freund, 1992, ISBN: 1-55899-133-6

Volume 240—Advanced III-V Compound Semiconductor Growth, Processingand Devices, SJ. Pearton, D.K. Sadana, J.M. Zavada, 1992,ISBN: 1-55899-134-4

Volume 241—Low Temperature (LT) GaAs and Related Materials, G.L. Witt,R. Calawa, U. Mishra, E. Weber, 1992, ISBN: 1-55899-135-2

Volume 242—Wide Ban-Gap Semiconductors, T.D. Moustakas, J.I. Pankove,Y. Hamakawa, 1992, ISBN: 1-55899-136-0

Volume 243—Ferroelectric Thin Films II, A.I. Kingon, E.R. Myers, B. Tuttle,1992, ISBN: 1-55899-137-9

Volume 244—Optical Waveguide Materials, M.M. Broer, H. Kawazoe,G.H. Sigel, R.Th. Kersten, 1992, ISBN: 1-55899-138-7

Volume 245—Advanced Cementitious Systems: Mechanisms and Properties,F.P. Glasser, P.L. Pratt, T.O. Mason, J.F. Young, G.J. McCarthy,1992, ISBN: 1-55899-139-5

Volume 246—Shape-Memory Materials and Phenomena—FundamentalAspects and Applications, C.T. Liu, M. Wuttig, K. Otsuka,H. Kunsmann, 1992, ISBN: 1-55899-140-9

Volume 247—Electrical, Optical, and Magnetic Properties of Organic SolidState Materials, L.Y. Chiang, A.F. Garito, DJ. Sandman, 1992,ISBN: 1-55899-141-7

Volume 248—Complex Fluids, D. Weitz, E.Sirota, T. Witten, J. Israelachvili,1992, ISBN: 1-55899-142-5

Volume 249—Synthesis and Processing of Ceramics: Scientific Issues,W.E. Rhine, T.M. Shaw, RJ. Gottschall, Y. Chen, 1992,ISBN: 1-55899-143-3

Volume 250—Chemical Vapor Deposition of Refractory Metals and CeramicsII, T.M. Besman, B.M. Gallois, J. Warren, 1992,ISBN: 1-55899-144-1

Volume 251—Pressure Effects on Materials Processing and Design,K. Ishizaki, E. Hodge, 1992, ISBN: 1-55899-145-X

Volume 252—Tissue-Inducing Biomaterials, M. Flanagan, L. Cima, E. Ron,1992, ISBN: 1-55899-146-8

Volume 253—Applications of Multiple Scattering Theory to Materials Science,W.H. Butler, P.H. Dederichs, A. Gonis, R. Weaver, 1992,ISBN: 1-55899-147-6

Volume 254—Specimen Preparation for Transmission Electron Microscopy ofMaterials III, R. Anderson, J. Bravman, B. Tracy, 1992,ISBN: 1-55899-148-4

Volume 255—Hierarchically Structured Materials, LA. Aksay, E. Baer,M. Sarikaya, D.A. Tirrell, 1992, ISBN: 1-55899-149-2

Volume 256—Light Emission from Silicon, S.S. Iyer, L.T. Canham,R.T. Collins, 1992, ISBN: 1-55899-150-6

Prior Materials Research Society Symposium Proceedingsavailable by contacting Materials Research Society.






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