Download - Fullerenes
Fullerenes
Adam D. DarwishDOI: 10.1039/b716501n
This chapter reviews the literature reported during 2007 on fullereneschemistry including fullerene production and properties, organic andorganometallic chemistry, endohedral derivatives and advanced materialsas well as theoretical studies and possible applications of fullerene and itsderivatives.
Highlights
The in vitro antitumour activity of a novel fullerene-maleic anhydride derivative
synthesized via radical polymerization has been tested and the result showed that the
derivative exhibits better antitumor activity against HeLa cells and bone tumour
cells. The antitumor mechanism of water-soluble fullerene derivative has been
investigated.1
1. Production, separation and properties of fullerenes
An integrated technology for the manufacture of C60 and C70 fullerenes with purity
exceeding 99.5 and 98.0 wt%, respectively, has been developed.2 Extractable
amounts of C60 and C70 fullerenes have been obtained by two-step pyrolysis of
PCF3 and high-temperature pyrolysis of two fullerene precursors-1,2 0-binaphthyl
and 1,3-oligonaphthylene. The formation of fullerenes was confirmed by MALDI-
TOF and HPLC analysis.4 Isolable quantities of C60 fullerene have been achieved by
flash pyrolysis of bromine-substituted truxenone derivatives.5 Size-tunable hexago-
nal C60 fullerene nanosheets have been prepared using a liquid–liquid interfacial
precipitation method. The prepared C60 nanosheets are porous, very thin, and
foldable in nature.6 Saturated C60 fullerenes with O2, N2 or Ar have been achieved
by precipitation of C60 from 1,2-dichlorobenzene solution saturated by these gases.
The structure and chemical composition of the fullerenes was characterized by
spectroscopic techniques.7
Onion-like fullerenes nanocarbons were synthesized in high yield and quality by
arc discharge in water between pure graphite electrodes at the current of 50 A. Many
spectroscopic techniques were employed to study the crystallography of these carbon
nanostructures.8 Comparative analysis of processes in carbon arc and RF plasma
during fullerene production has been presented. It has been found that the zone of
fullerene formation is significantly larger in RF plasma reactor compared to arc
reactor.9
An overview of the synthesis and characterization of different types of fullerene
dimers such as directly bonded dimers, a short chain C60 dimer and other dimers
with bridge molecules of varying length have been presented.10
Department of Chemistry, School of Life Sciences, University of Sussex, Falmer, Brighton,UK BN1 9QJ. E-mail: [email protected]; Fax: 01273606196; Tel: 01273 678474
REVIEW www.rsc.org/annrepa | Annual Reports A
360 | Annu. Rep. Prog. Chem., Sect. A, 2008, 104, 360–378
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Cage-opened C59 fullerenones with 18- and 19-membered-ring orifices has been
prepared through peroxide-mediated stepwise cleavage of fullerene skeleton bonds.
C59 fullerenones were found to encapsulate water under mild conditions as char-
acterized by spectroscopic data and single-crystal structures.11
Systematic separation and quantification of C60 and C70 fullerenes using thermo-
stated micro thin-layer chromatography have been studied. The reported separation
protocol shows a capability for the evaluation of fullerenes quantity in commercial
samples.12 Remarkable improvement in efficiency of filtration methods for fullerene
purification has been achieved by using 1,2,4-trimethylbenzene as solvent.13 It has
been found that the encapsulation of fullerenes with a cyclotriveratrylene derivative
system was preferred for the separation of C84 fullerene from fullerenes mixture.14
The toxicity of C60 fullerene and its derivatives have been reviewed.15 Toxicity
evaluation of C60, C70 and C60(OH)24 in vivo using embryonic zebrafish show’s that
C60(OH)24 is significantly less toxic than C60. These studies also suggest that the
embryonic zebrafish model is well-suited for the rapid assessment of nanomaterial
toxicity.16
The increase of fullerene nanoparticle additives was found to improve the
lubrication properties of regular mineral oil.17 The effect of C60 fullerene water
suspension on bacterial phospholipids and membrane phase behaviour has been
investigated. It has been shown that the response in lipid composition and
membrane phase behaviour depends on both the fullerene concentration and the
cell wall morphology.18 The binding abilities of calix[5]arene-based host molecules
for higher fullerenes in organic solvents and the structure of the host–guest complex
of double-calix[5]arene and C76 have been investigated.19
The solubility of C60 fullerene in long chain fatty acids esters have been tested, It
has been found that C60 is not only soluble in the fatty acid esters but is also reactive
with them under mild conditions. The C60 solubility in vegetable oils may pave the
way for easier application of C60 fullerene in medicinal chemistry and in additive
chemistry for varnishes and fuels.20 The solubility of C60 fullerene in toluene was
found to increase with increasing pressure, and then decreased with a sharp
maximum, suggesting a transition between solid phases.21 The solubility of C60 in
water and other conventional organic solvents was remarkably improved by grafting
hydrophilic PEO onto C60 using macroazo initiators. In addition, the thermal
stability of PEO was dramatically increased by grafting onto C60 fullerene.22 The
solubilisation of C60 in water in the presence of aquatic HSs was found to be 8–540
times higher than that in the blank solution.23 Thermodynamic properties of C60
solutions in individual and mixed organic solvents,24 and polythermal solubility of
C60 and fullerene mixture in higher isomeric carboxylic acids have been studied
within the 20–80 1C range.25,26
Fullerene C60 as a superefficient quencher of singlet exited states of PAH has been
found by the quenching of fluorescence of PAH by C60 in ethylbenzene at 293 K. The
overlap integrals of the PAH fluorescence spectra with the C60 absorption spectrum
and the critical energy transfer distances have been calculated.27
The effect of the C60 and C70 fullerene contents on the dielectric properties of
polyimide films has been presented. It has been found that the modification of
polyimide with C70 has no significant influence on time constants, while increasing
the amount of C60 leads to shorter beta-relaxation time.28
Relative stabilities of six C74 fullerene cages have been evaluated using the Gibbs
energy in a broad temperature interval. The computations indicate that the isolation
of other C74 cages, in addition to the IPR isomer, is less likely though not
Annu. Rep. Prog. Chem., Sect. A, 2008, 104, 360–378 | 361
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impossible.29 DFT calculations were carried out to study the reactivities of Ih C60
and D5h C70 fullerenes. It was found that some of the C70 sites have larger reaction
energies than that of C60, although C70 is energetically more stable than C60
fullerene.30
2. Chemistry of the fullerenes
2.1 Organic chemistry
2.1.1 Addition reactions. Advancements and prospects of [2+2] cycloaddition to
C60 fullerene, including classic reaction, the main reagent as well as the reaction
mechanism have been reviewed.31
Azomethine ylides obtained from the reaction of picolylamines and aromatic
aldehydes undergo highly regio- and stereo-selective [2+3] cycloaddition reactions
with C70 fullerene. CV studies of the synthesised pyrrolidinofullerenes showed the
existence of some electronic communication between the substituents in the pyrro-
lidine ring and the C70 fullerene cage.32 Two series of oligofluorene–C60 and C60–
oligofluorene–C60 donor–acceptor conjugates have been synthesized from CHO–
Y1�5 and CHO–Y1�5–CHO precursors (Y = 9,9-dihexylfluorene-2,7-diyl) via
1,3-dipolar cycloaddition reaction of in situ generated azomethine ylides with an
excess of C60. The energy transfer properties for the products have been studied.33
The 1,3-dipolar cycloaddition reaction has been used to prepare N,N-dimethylani-
line-pyrazolinoC70-ferrocene from the reaction of nitrile imine with C70 fullerene. It
was found that the pyrazolino ring mediates a CS between the donor moieties and
the photoexcited C70 moiety.34 C60 fulleropyrrolidine-containing poly(benzyl ether)
dendrimers were prepared through 1,3-dipolar cycloaddition of amino acid, alde-
hyde derivatives and C60 fullerene. Their dielectric and electrooptical properties in
solution have been studied.35
Synthesis and kinetic stability of Diels–Alder adducts of substituted isobenzofur-
ans,36 cis-1 bis(isobenzofuran)37 and C60 have been investigated. Four new adducts
were obtained via microwave-assisted Diels–Alder [4+2]-cycloaddition reaction of
chiral heterodienes with C60 fullerene. Adducts were fully characterized by elemental
and spectroscopic analysis.38 The reactive 4,7-diphenylisobenzofuran was utilized to
form new three-, four-, and five-ring acenes via Diels–Alder reaction and the latter
compound was reacted with C60 fullerene to produce new C60-acene adducts.39 A
molecular tweezers C60H28 with two corannulene pincers and a tetrabenzocyclooc-
tatetraene tether was obtained from double Diels–Alder addition of isocorannule-
nofuran to dibenzocyclooctadiyne followed by deoxygenation.40
The formation of methanofulleroid adducts of Y3N@C80 have been achieved via
cycloaddition of bromomalonates to Y3N@C80. Full characterization of these
derivatives has been described including spectroscopic and electrochemistry analysis.
DFT calculations were also presented.41
A Bingel reaction has been used to synthesise C60–oligocarbazole dendrons. Their
fluorescence and transient absorption spectra have been presented.42 A donor–
acceptor subphthalocyanine fused dimers–C60 dyads has been prepared through
double cycloaddition of the fused dimer. The product was characterized using
photophysical and electrochemical techniques, together with theoretical study.43
The regioselective addition reaction of an aromatic hydrazine or hydrazone to
isomeric diketone derivatives of C60 have been used to synthesise ten new open-cage
fullerene derivatives with 16-membered-ring orifice in high yields.44
362 | Annu. Rep. Prog. Chem., Sect. A, 2008, 104, 360–378
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Pyrrolofullerenes have been synthesised in high yields through cycloaddition of
tertiary amines to C60 fullerene, catalyzed by Ti, Zr, and Hf complexes.45
It has been found that thermal treatment of isoxazolino[4,5:1,2]–C60- and C70-
fullerenes in the presence of an excess of a dienophile and Cu(II) catalyst undergo an
efficient retro-cycloaddition reaction to pristine fullerenes.46 Eglington-Glaser cou-
pling reaction has been used to prepare a triptycene-based nanosized molecular cage,
and its structure was determined by spectroscopic analysis.47
1,3-Dipolar cycloadditions of C2v–C82 with N-methylazomethine have been
studied at the PM3 level, and their mechanism and regiochemistry have been
investigated.48
2.1.2 Hydrogenation. Hydrogenation of C60, C70 and higher fullerene has been
obtained in high yield by using polyamines at elevated temperatures. It has been
found that the hydrogenation reaction times can be reduced to minutes by using a
microwave reactor. The mechanism of polyamine hydrogenation was discussed.49
DFT calculations showed that the hydrogenated silicon fullerene is stable over
hydrogen molecule attack. It is demonstrated that up to 58 hydrogen molecules can
be stored into its interior cavity, and together with 60 hydrogen atoms in the exterior
surface, total gravimetric density of hydrogen of 58H2@Si60H60 amounts to 9.48%,
which is much higher than any reported capacity of hydrogen storage in other
media.50
Thermodynamic properties, molecular structures and vibration frequencies were
studied for 9 isomers of C60H36 by theoretical methods.51 The geometrical structures,
electronic properties, and spectroscopic properties of non-IPR fullerene C66 and its
derivatives C66X4 (X=H, F, Cl) have been studied by the first-principle calculations
based on DFT.52 Systematic density functional studies on the stabilities
and electronic properties of seven-membered ring C58X18 fullerene derivatives
(X = H, F, and Cl) have been performed.53
2.1.3 Alkylation and arylation. A modified hot filament chemical vapour deposi-
tion method has been used for direct methylation of C60 via a gas-phase reaction in a
CH4/H2 atmosphere.54 A functionalized fullerene (R–C60–H; R = aryl, heteroaryl,
and alkenyl) with good to excellent selectivity have been achieved by treatment of
C60 with the corresponding organoboron compound in the presence of a catalytic
amount of [Rh(cod)(CH3CN)2]BF4 in water/o-dichlorobenzene.55 Synthesis, electro-
nic and excited state properties of fullerene derivatives functionalized with isomeric
phenyleneethynylene-based dendrons possessing either 1,3,5-triethynylbenzene or
1,2,4-triethynylbenzene branching units have been reported.56
A range of C60-long alkyl chain derivatives have been synthesized and inserted
into SWCNT and used toward controlled spacing in one-dimensional molecular
chains.57 1,2-dibenzyl C60 has been obtained from the reaction between C602� and
benzyl bromide in benzonitrile containing 0.1 M TBAP, purified using HPLC and
characterised by spectroscopic analysis.58
2.1.4 Polymerisation. The design, characterisation and application of conjugated
polymers electron-accepting with tethered moieties as ambipolar materials for
photovoltaic cells have been reviewed.59
An overview on fullerene-containing polymers, from synthesis to their physico-
chemical properties in solution has been reported.60
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C60–PEO–C60 has been prepared by reacting azido-terminated PEO with C60. The
self-organization behaviour of such C60-modified copolymers in different mixtures of
chloronaphthalene and benzene was studied by a combination of static and dynamic
laser light scattering.61 C60-cored star polyfluorenes have been synthesized in high
yield by using Prato reaction and bulky fluorene addends. Annealing studies
indicated that the C60-cored star polyfluorenes were of good colour stability.62
The copolymerization of C60-cyclopentadiene cycloadducts and norbornene in
varying ratios gave a series of C60-containing polymers. The co-polymers formed
have been investigated by spectroscopic and thermal techniques.63 The methods of
synthesis of poly(urethanes) that were based on hydroxyfullerenes, afforded linear,
network, and star-shaped polymers containing a covalently bonded fullerene. The
physical, physicochemical, and mechanical properties of fullerene-containing poly-
(urethanes) have been described.64 The electropolymerization of terthiophene S,S-
dioxide-fullerene Diels–Alder adduct produces donor–acceptor molecular wires
providing a new way to fullerene-based double cable polymers.65
Nanofiber material which exhibits an ohmic conductance response at elevated
temperature has been obtained by mixing solutions of p-Butcalix[5]arene and C60 in
toluene.66 General method for the preparation of ultrathin, large-area, free-standing
films of nanofibrous composite materials has been developed and their optical,
biological, metallic, and magnetic properties have been reported.67
The reaction between C60Br24 and C70Br10 with TiCl4, afforded singly-bonded
dimeric structures (C60Cl5)2 and [(C70)2](Ti3Cl13)2, respectively.68 A chiral dumbbell
shaped bis(C60)-oligoelectrolyte has been synthesized by connecting two C60 cores
with a chiral cyclo-bis(malonate), followed by the regioselective addition of ten
amino-terminated malonates into the octahedral positions of the fullerene moieties
and subsequent cleavage of the protecting groups.69
A DFT study on the dimerization of C62, H2–C62, and F2–C62 were showed that
all isomers of the H2–C62 dimer are appreciably more stable than the individual
monomers. Although a large steric repulsion due to F atoms significantly reduces the
stability of F2–C62 dimer, its two isomers were still more stable than separate
monomer.70
2.1.5 Fullerene derivatives containing halogens. Synthetic methods, structures and
general properties of halogenated and perfluoroalkylated fullerenes in recent years
have been reviewed. Fluorinated fullerene and their derivatives were especially
described.71 Methods for the synthesis and structure of polyfluoro (chloro, bromo)
derivatives of C60 fullerene have been described. The reactivity of these compounds
including redox reactions, nucleophilic substitution, radical addition, cycloaddition
and electrophilic arylation has been demonstrated.72 C60(CF3)8 has been prepared by
a reaction of C60 with CF3I at 420 1C followed by HPLC separation and molecular
structure determination.73
The thermal reaction of C60 or S6–C60(CF3)12 isomer with CF3I produced new
isomers of C60(CF3)12 and C60(CF3)14 which have been isolated and characterized by
single crystal X-ray diffraction and investigated theoretically by means of DFT
calculations.74
It has been reported that the C1–C60(CF3)12 prepared from C60 with CF3I at
500 1C, exhibits an unusual fullerene(CF3)12 addition pattern that is 40 kJ mol�1 less
stable than the previously reported C60(CF3)12 isomer.75 Three isomers of
C60(CF3)16 and one isomer of C60(CF3)18 have been isolated by HPLC from a
364 | Annu. Rep. Prog. Chem., Sect. A, 2008, 104, 360–378
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mixture prepared by trifluoromethylation of C60 with CF3I in a glass ampoule at
380–400 1C. The structure of the isomers has been determined by X-ray single
crystallography and their relative stabilities have been reported according to the
DFT calculations.76 A number of C60(CF3)2�10 compounds have been synthesized
by the reaction of C60 with silver trifluoroacetate and successfully isolated by means
of HPLC. The structures and theoretical study of lower trifluoromethyl derivatives
were reported.77
Novel C60(CF2)1�3 compounds with unique [6,6]-open structures have been
formed from either refluxing of the o-dichlorobenzene solution of C60 with
CF2ClCO2Na and 18-crown-6 or by the thermal decomposition of CF2ClCO2Na.
A theoretical survey of CF2 derivatives of C60 has been reported.78,79 Eight isomers
of pentafluoroethyl C60 derivatives C60(C2F5)n (n= 6, 8, and 10) were synthesized by
the reaction of C60 with C2F5I at 380–440 1C and isolated by chromatographic
separation. Their molecular structures were established by X-ray diffraction and
their relative stabilities were compared by DFT calculations.80 Seven isomers of
C70(C2F5)10 have been synthesised by a reaction of C70 with C2F5I at 350 1C
followed by HPLC separation and crystal structure determination.81
Pure isomers of composition C60(C4F8)2 (two isomers), C60(C4F8)6 and C70(C2F4)2have been produced from addition reaction of biradicals thermally generated from
C2F4I2 with C60 and C70 fullerenes.82 C78F42 is the first example of a perfluoro-
alkylfullerene with perfluoroisopropyl groups, its structure was found to
be 1,7,16,30,36,47-hexakis(perfluoroisopropyl)-1,7,16,30,36,47-hexahydro(C60-Ih)-
[5,6]fullerene.83 It has been found that C60F30, is one of six isomers of C60(CF3)10that have been isolated and its structure was determined as 1,6,11,18,-
24,27,33,51,54,60-decakis(trifluoromethyl)-1,6,11,18,24,27,33,51,54,60-decahydro-
(C60-Ih)[5,6]fullerene.84
X-ray photoelectron and X-ray emission spectroscopic studies of C60F24 of the Th
symmetry contains two types of chemically different carbon atoms revealed a
difference in the widths of the X-ray bands corresponding to these types of atoms.85
Electrochemical, spectroscopic, and DFT studies of C60(CF3)2�18 have been
reported.86 Bond orders and atomic properties of C60F18 and C60Cl30 derived from
their charge densities were analyzed by using Bader’s atoms in molecules theory.87
2.1.6 Fullerene derivatives containing nitrogen. Chemically cross-linked C60 thin
films capable of binding silver nanoparticles have been prepared by direct solvent-
free functionalization of C60 fullerene with 1,8-diaminooctane.88 Vicinal aminohy-
droxy fullerene compounds with the amino group on the central pentagon have been
obtained from the reaction of fullerene peroxides C60O(OOBut)4 with ammonia or
with nonbulky primary amines. The bromo group in C60(OH)(Br)(OOBut)4 has been
replaced by ammonia and primary amines under the same condition. These
compounds have been characterized by spectroscopic means, and X-ray single-
crystals.89 Aminomethano-C60 fullerenes, has been generated in situ by the treatment
of their trifluoromethanesulfonic acid salts with a base, these were readily converted
into 1-acyl-1,2-dihydro-C60 fullerenes via the ring opening of the cyclopropane
moiety.90 A new family of N-(2,4-dinitrophenyl)-2-pyrazotino-C60 fullerene deriva-
tives has been synthesized by electrophilic nitration using nitronium triflate.91
Catalytic 1,2-hydroamination of C60 fullerene with primary and secondary amines
in the presence of Ti, Zr, and Hf complexes gave the corresponding alkyl-, aryl-,
and hetaryl-aminodihydrofullerenes.92 Synthesis, characterization, antioxidant
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properties, and solid-phase peptide synthesis of a series of C60 and C70 fullerene
phenylalanine and lysine derivatives have been achieved by the condensation of 1,2-
(40-oxocyclohexano)fullerene with the appropriately protected (4-amino)phenyl-
alanine and lysine, respectively. These compounds have been characterized by
spectroscopic techniques.93 A soluble C60 fullerene bearing triazole groups as an
electron transport moiety has been synthesized and characterized.94
The monoadducts of C60 with only [6,6]-closed isomer structure have been
obtained from the reaction of C60 fullerene with nitrile ylides generated from N-
benzyl-4-nitrobenzimidoyl chloride/N-(4-chlorobenzyl)-4-nitrobenzimidoyl chloride
and triethylamine.95
2,2-C60 fullerenoalkylamines have been synthesised from 2,2-C60 fullerenoalka-
noyl azides, which were generated from the corresponding chlorides through the
Curtius rearrangement in the presence of tert-butyl alcohol, followed by debutyla-
tion and decarboxylation under acidic conditions.96 Condensation of 1,2-dicyano-
fullerene and phthalonitrile derivatives in the presence of nickel chloride in quinoline
gave novel tetraazachlorin–C60 fullerene conjugates. The electronic structures of the
conjugates have been investigated in detail using spectroscopic and electrochemical
techniques with the aid of DFT calculations.97
Two new pyrazolo- and isoxazolo-C60 fullerenes covalently linked to vinylene-
phenylene bearing electron-donor groups attached in the periphery have been
synthesized. The photo-physical properties of these dual-donor derivatives have
been investigated.98 Synthesis and electrochemical properties of new cymantrenyl
and styryl derivatives of 1-methyl-C60-fullereno[c]pyrrolidine have been described.99
Oxy aminated C60 and C70 fullerenes have been prepared in high yield via the
reaction of fullerenes with excess secondary amine in the presence of cumene
hydroperoxide oxidant.100
2.1.7 Fullerene derivatives containing oxygen. Highly oxidized C60 with an
average similar to 29 oxygen additions per molecule, arranged in repeating hydroxyl
and hemiketal functionalities have been obtained from the reaction between C60 as a
nanoscale suspension, and dissolved ozone in the aqueous phase. The oxidized
fullerenes were characterised by spectroscopic techniques.101 Novel C60 fullerene
acetals and ketals have been obtained by the reaction of C60 with corresponding
aldehydes or ketones and alkoxide in anhydrous chlorobenzene, the presence of air
at room temperature. A possible reaction mechanism for the formation of the
fullerene acetals and ketals has been proposed.102 Reactions of C60 fullerene-fused
lactones with methylmagnesium bromide and diisobutylaluminum hydride afforded
rare fullerene hemiketals and hemiacetals, which were dehydrated by polyphos-
phonic acid to the corresponding C60 fullerene-fused dihydrofurans.103 Polyacryl-
amide gel electrophoresis have been used to separate a mixture of synthesised
polyhydroxylated fullerenes, C60(OH)n and their esters. The chemically modified
fullerol as a fluorescent indicator has been proposed.104 Two-step grafting method
has been developed to produce hydroxyl fullerene C60(OH)3–12. The regioselectivity
of the hydroxyl groups has been determined by high-resolution solid-state NMR
analysis.105
The efficient conversion of bromofullerene to alkoxyfullerenes has been achieved
by using visible light irradiation or in the presence of silver salt.106 Oxidation of C60
and C70 powdered crystals has been produced by exposure to ozone in the presence
of oxygen. The infrared spectra of oxidised fullerenes showed absorption bands
366 | Annu. Rep. Prog. Chem., Sect. A, 2008, 104, 360–378
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indicating that oxidation was accompanied by formation of unsaturated carboxylic
groups, aldehyde and other ketonic moieties.107 Fulleropyrrolidine di- and tri-
carboxylic acids have been produced from the hydrolysis of the corresponding
fulleropyrrolidine derivatives generated using photochemical reaction of C60 with
corresponding iminodiacetic methyl ester. Fulleropyrrolidine derivatives were struc-
turally characterized by spectroscopic methods and elementary analysis.108 Full-
erene-mixed peroxide to open-cage oxafulleroid C59O3(OH)2((OOBu)But)2embedded with furan and lactone motifs have been reported.109 Stability studies
of epoxy methylated C60 fullerenols using desorption or in-beam electron impact
mass spectrometry showed that the epoxide derivative was stable under spectro-
metric conditions.110
The structural and electronic properties of the highest and more stable epoxyge-
nated fullerenes C60O30 have been determined using ab initio and DFT calcula-
tions.111
2.1.8 Fullerene derivatives containing sulfur. A novel open-cage C60 fullerene
derivative, having two sulfur atoms on the rim of its 13-membered-ring orifice, has
been isolated and characterized.112 A 2-pyrazolino–C60 fullerene-based triad, pos-
sessing two TTF units connected with flexible long linkages, has been prepared and
their fluorescence properties were discussed.113 A series of pi-extended TTFs bearing
one or two dibenzylammonium units have been threaded through a dibenzo-24-
crown-8 ring covalently linked to a C60 sphere. These supramolecular molecules have
been prepared either by a multistep synthetic procedure involving Sonogashira
cross-coupling reactions or by direct esterification reactions leading to more flexible
systems. Complexation experiments carried out by H1 NMR titration and fluores-
cence studies together with UV/Vis and CV have been presented.114 Thiacalix[4]-
arene-porphyrin conjugate has been prepared and its high selectivity complexes with
C70 fullerene in solution was presented.115
Sulfide-bearing imines of glycine esters have been used to prepare dihydro-
pyrrolo-C60 fullerene derivatives containing a sulfide, an imine, and an ester
functionality for further chemical transformations and characterized using spectro-
scopic methods.116
2.2 Organometalic chemistry
The main synthetic procedures to obtain IF nanoparticles have been reviewed
alongside with the different mechanisms that affect the morphology of the final
product.117 IF MoS2 nanoparticles have been synthesised by reaction of sulfur
powder and ammonium molybdate in the presence of H2 atmosphere at 600 1C. The
products were characterized by spectroscopic techniques, and the possible growth
mechanism has been proposed.118 IF-Mo1-xNbxS2 nanoparticles have been synthe-
sized by a vapour-phase reaction involving the respective metal halides with H2S.
These nanoparticles were found to exhibit interesting single electron tunnelling
effects at low temperatures.119 Silicon-doped heterofullerene C52Si8 and C62Si8 have
been obtained for the first time by an arc synthesis at atmospheric pressure.120
C60-polyethoxysiloxanes have been prepared by cohydrolytic polycondensation of
C60-triethoxysilylated obtained from the hydrolysilylation of C60 with triethoxysi-
lane in the presence of platinum catalyst with tetraethoxysilane in a molar ratio of
Si/C60 10:1000 under nitrogen atmosphere. The optical limiting properties of their
free-standing films were evaluated.121
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Synthesis, characterization, and electrochemical properties of new transition metal
fullerene complexes containing cis-Ph2PCHQCHPPh2 ligands have been re-
ported.122 A series of zinc porphyrin–C60 fullerene dyads linked by conformation-
constrained tetrasilanes and permethylated tetrasilane have been synthesized for the
evaluation of the conformation effect of the tetrasilane linkers on the photoinduced
electron transfer.123 The first multicomponent species containing a luminescent Ir(III)
subunit and a functionalized C60 moiety have been prepared and their phosphores-
cence properties investigated.124 Thermally stable C60-poly(dichlorophosphazene)
has been produced by a novel approach via thermal ring-opening polymerization
phosphonitrile chloride trimer in the presence of C60 fullerene.125 The synthesis of a
new open-cage C60 fullerene containing selenium together with its behaviour when
encapsulating and releasing molecular hydrogen have been reported.126 The pre-
liminary inclusion properties of silver(I)N-heterocyclic carbene-bridged calix[4]arene
synthesized by a fragment-coupling approach showed that it is a novel efficient C60
fullerene fluorescent sensor.127 Two new fulleropyrrolidine-oligothienylenevinylene-
ferrocene triads C60–nTV–Fc (n = 2, 4) have been synthesized and their photo-
induced CS processes were investigated. It has been revealed that the introduction of
a ferrocene donor moiety at the end of the longer nTV chain in the C60–nTV dyad
systems effectively increases the CS efficiency and the lifetimes of CS states.128
The formation mechanism, geometric structures, and electronic properties of a
metal-substituted fullerene C58Fe2 have been studied using FOT and DFT.129
2.3 Advanced materials
The processes and limitations that govern device operation of polymer-fullerene
BHJ solar cells, with respect to the charge-carrier transport and photogeneration
mechanism have been reviewed.130 A series of covalent C60–OPV dyads, dendrimers
with an OPV core and peripheral C60 subunits and supramolecular C60–OPV
conjugates have been prepared. Their photophysical properties have been exten-
sively studied. It has been suggested that the wire-like behaviour of the OPV units
linking the C60 acceptor to various donors opens the way to related compounds as
integrated components in the construction of optoelectronic devices and nano-
technology.131
Photovoltaic devices fabricated from a blend of regioregular P3HT and fullerene
have been studied. It was found that post-annealing of the devices for an optimum
duration and temperature improves the solar cells, and the power conversion
efficiency of the devices increases to 2.1% at AM 1.5.132 The preparation of P3HT
nanofibers in highly concentrated solutions, which enables the fabrication of
nanostructured films on various substrates, along with their characterization in
solution and in the solid state have been detailed.133 Photovoltaic cells based on
solution-processed blends using a novel anthradithiophene derivative as the donor
and a fullerene derivative as the acceptor have been reported. A direct correlation
between coverage of a device with spherulites and its performance were observed.134
The photovoltaic performance of BHJ solar cells from polyterthiophene/fullerene
composites has been discussed and compared to the polymer/fullerene blend
morphology.135
Wittig condensation has been used to synthesize a series of new novel building
blocks for donor–acceptor conjugated polymers containing perylene, PPV and
fullerene. All of the polymers have been characterized by spectroscopic techni-
ques.136 FETs based on P3HT and PCBM films have been studied for various
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structures with metal electrodes on a SiO2/Si substrate. FET characteristics in
various configurations (top and bottom) of contact with Au and Al were examined
in P3HT and PCBM films.137 Polymer PVK–C60, as donors–acceptors in a molar
ratio of about 100:1, has been synthesized via covalent tethering of C60 to PVK. The
molecular structure and composition of the polymer was characterized by spectro-
scopic methods. Nonvolatile polymer memory devices based on bistable electrical
switching in a thin film of PVK–C60 have been investigated.138
Two new water-soluble Gd-containing endohedral metallofullerenes
[ScxGd3�xN@C80O12(OH)26 (x = 1, 2), have been synthesized and characterized
by spectroscopic techniques. Their observed RI values for water protons indicates
that these trimetallic nitride endohedral fullerenols are potential next-generation
high-efficiency MRI contrast agents.139 Preliminary studies into the use of fullerene-
functionalised poly(terthiophenes) polymers as a cathode materials in a lithium
battery have been investigated.140
3. Endohedral fullerenes
Synthesis, stability, and suitability for radio immunotherapy of Pb-212@C60 and its
water-soluble derivatives have been presented.141
HPLC has been used to isolate two new trimetallic nitride endohedral fullerenes,
Gd3N@C84,88. They were characterized by spectroscopic techniques and their
electrochemical properties were discussed.142 High yield of Sc3N@C80 metallofuller-
ene and fullerene extract have been achieved via filling cored graphite rods with
copper and Sc2O3 only during the production. The weight percent of Cu added to the
rod was found to effect the type and amount of fullerene produced.143 High-
temperature radical reaction of Sc3N@C80 isomers with gaseous CF3I has resulted
in the isolation of Sc3N@{C80-Ih}(CF2)2 and Sc3N@{C80-D5h}(CF2)2 which have
idealized C2 and Cs symmetry, respectively. Both compounds were characterized by
spectroscopic techniques and DFT calculations.144 The first N-tritylpyrrolidino
derivatives of D3h-Sc3N@C78 have been successfully synthesized and isolated. The
adducts were characterized by NMR experiments and DFT calculations.145 A series
of endohedral fullerenes Sc3�xYxN@C80 (x = 0–3) with variable encaged moieties
and the same C80 cage have been synthesized, isolated, and spectroscopically
characterized. Their comparative spectroscopic and reactivity were studied.146
The synthesis and characterisation of the new endohedral cluster fullerene
Sc3CH@C80 has been reported. The extensive characterisation by spectroscopic
techniques and DFT calculations provided the evidence for the caging of Sc3CH
clusters inside C80 with icosahedral symmetry.147 The first studies on the stable
paramagnetic cation of non-IPR cluster-fullerene Sc3N@C68 have been carried out
using ESR/UV-Vis-NIR spectroelectrochemistry.148 Two new isomers of Eu@C72
have been synthesized, and isolated by HPLC and characterized by spectroscopic
methods.149 The structures of the newly synthesized endohedral fullerenes Tb3(N@C88, Tb3N@C86, and the Ih and D5h isomers of Tb3N@C80 have been
determined by single-crystal X-ray diffraction.150 The insulating properties of
polyhydroxylated metallofullerene film of Gd@C82(OH)12 has been studied using
synchrotron radiation UPS and TEM techniques. It has been reported that the
insulating properties can be controllably tuned into semiconducting ones as a
function of temperature.151 The water-solubilizing process of Gd@C82 with hydro-
xylation reaction using mass spectrometry techniques has been quantitatively
studied.152
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Gibbs-energy based evaluations of the production abundances for two C74-based
endohedral Mg@C74 and Ca@C74 have been presented.153
4. Applications of fullerene derivatives
The aspects of medicinal applications of fullerene derivatives have been reviewed.154
The physicochemical properties and biomedical applications of Gd@C60 especially
in regard to the unique benefits of this novel class of materials for MRI have been
reviewed.155
The anionic gadofullerene {Gd@C60[C(COOH)2]10} was found an attractive
candidate for ex vivo labeling and noninvasive in vivo tracking of any mammalian
cell via MRI.156 Synthesis, structure and biological activity of two new nitroxide
methanofullerenes have been reported. It has been found that malonate nitroxide
methanofullerene in combination with the known anticancer drug cyclophospha-
mide showed high antitumor activity against leukemia P-388.157 The multiple
mechanisms underlying the in vitro anticancer effects of the C60 fullerene water
suspension (nano-C60 or nC60) produced by solvent exchange method have been
demonstrated. The results provide grounds for further development of nC60 as an
anticancer agent.158
It has been reported that the star-shaped C60-containing nanostructured poly-
meric materials were promising candidates for photodynamic cancer therapy and
treatment of multidrug resistant pathogens.159 The efficacy of fullerenol C60(OH)24and amifostine in the protection of rats against harmful effects of ionizing radiation
has been studied. The results confirm satisfactory radio protective efficacy of
fullerenols and encourage further investigations as potential radioprotectors.160
The studies of the potential of a strong free-radical scavenger, water-soluble C60
fullerene, as a protective agent against catabolic stress-induced degeneration of
articular cartilage in osteoarthritis (OA), both in vitro and in vivo, indicates that C60
fullerene is a potential therapeutic agent for the protection of articular cartilage
against progression of OA.161 A new biological function for fullerenes which may
represent a novel way to control mast cell-dependent diseases including asthma,
inflammatory arthritis, heart disease, and multiple sclerosis has been demon-
strated.162
The effects of two water-soluble fullerene derivatives, fullerol and C60-trimalonic
acid on PCR have been investigated. Both derivatives were found to inhibit PCR in a
dose-dependent manner.163 Pure novel water soluble C60 and C70 fullerenes deriva-
tives have been prepared and their antioxidant activities studied. These results
indicate that dendritic water soluble C60 monoadducts exhibit the highest degree
of antioxidant activity against superoxide anions in vitro as compared with tris-
malonate-derived anionic fullerenes as well as cationic fullerenes of similar overall
structure.164 Synthesis, characterization, preliminary study on in vitro antioxidant
activity as well as the steady state photophysical properties of four new covalent
fullero-steroidal conjugates have been presented. These fullero-steroidal compounds
represent good candidates for potential antioxidants as well as pro-oxidants.165 The
antioxidant and cytoprotective effects of a series of new water-soluble fullerenes have
been compared by using zebrafish embryos as a model system.166
Silica particles of different porosity were modified with aminopropyl linker and
then covalently bound to C60-fullerenoacetic acid or C60-epoxyfullerenes and used
for purification of biomolecules of different characteristics.167 A novel organo-
phosphate-containing water-soluble derivative of C60 has been synthesized. The
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influence of these nanoparticles on the conformational changes of HSA has been
investigated by biophysical methods.168
A fullerene bilayer membrane formed by dissolution of a water-soluble fullerene,
Ph5C60K, has been shown to be several orders of magnitude less permeable to water
than a lipid membrane, and the permeability decreases at higher temperature. These
findings provide possibilities of membrane design in science and technology.169 The
synthesis of the first endohedral fullerene superconductors, K3(Ar@C60) and
Rb3(Ar@C60) having critical temperatures of about 18 and 27 K, respectively have
been reported.170
Highly water-soluble polycarboxylic fullerene derivatives have been prepared
from C60Cl6 and the corresponding methyl esters of phenylacetic and benzylmalonic
acids. The fullerene salt of these compounds showed pronounced anti-HIV action
and low toxicity.171 The use of fullerene substituted phenylalanine amino acid as a
passport for peptides through cell membranes have been demonstrated.172 Influence
of C60 and C60 containing composites of aminopropylaerosil on erythrocytes
resistance to the acid haemolysis and viability of thymocytes, Erlich ascitic carci-
noma and leukemia L1210 cells have been studied. It is shown that these new
materials can be used in bionanotechnology.173 Cationic poly-N,N-dimethylfuller-
opyrrolidinium derivatives have been designed and synthesised to complex plasmid
DNA for gene delivery.174
The photodynamic activity of six functionalized fullerenes with 1, 2, or 3
hydrophilic or 1, 2, or 3 cationic groups have been investigated. It has been
concluded that certain functionalized fullerenes have potential as novel PDT agents
and phototoxicity may be mediated both by superoxide and by singlet oxygen.175 A
pyropheophorbide-a-fullerene hexakis adduct immunoconjugate has been synthe-
sised as a modular carrier system in vitro testing for PDT.176
Intracellular uptake of water-soluble lipid-membrane-incorporated C60 with a
cationic surface into HeLa cells was found to induce cell death under visible light
irradiation in high efficiency.177
A novel beta-alanine C60 derivative has been synthesised and characterized using
spectroscopic and elemental analysis. Its scavenging ability to ROS both in vivo and
in vitro of rat pheochromocytorna cells has been measured. The results suggest that
the beta-alanine C60 derivative has the potential to prevent oxidative stress-induced
cell death without evident toxicity.178
A novel water-soluble cystine C60 derivative has been synthesised and character-
ized by spectroscopic techniques. Investigation of cystine C60 derivative potential
protective effects suggests that it has the potential to prevent oxidative stress-induced
cell death without evident toxicity.179
The study of interaction of new carboxyfullerenes with transport proteins at the
molecular level provides a model of fullerene-based nanomaterial interaction with
biomolecules and how these are transported in biological systems.180 Carboxyfuller-
enes were found to penetrate human keratinocytes, localize within mitochondria
where they act both by scavenging free radicals and by protecting cells from
apoptosis.181
The potential for polyhydroxylated fullerene to impact virus populations in both
natural and engineered systems ranging from surface waters to disinfection tech-
nologies for water and wastewater treatment has been investigated.182 Growth and
characterization of thin films containing fulleropyrrolidine derivatives and water
soluble porphyrins for solar energy conversion applications have been investi-
gated.183
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The effect of fullerene black additives on the antifriction properties and wear
resistance of fluoroplastics in sliding friction against steel with water lubrication has
been examined.184
New abbreviations
BHJ bulk heterojunction
CS charge-separation
CV cyclic voltammetry
FETs Field-effect transistors
FOT frontier orbital theory
IF inorganic fullerene-like
HAS human serum albumin
HSs humic substances
MALDI-TOF matrix-assisted laser desorption ionization-time of flight
NIR near infrared
OA osteoarthritis
PAH polycyclic aromatic hydrocarbons
PCF perchlrofulvalene
PCR polymerase chain reaction
PDT photodynamic therapy
PEO poly(ethylene oxide)
PPV poly(p-phenylenevinylene)
PVK poly(N-vinylcarbazole)
RF radio frequency
RI longitudinal relaxivities
TBAP tetra-n-butylammonium perchlorate
TV thienylenevinylene
UPS ultraviolet photoelectron spectroscopy
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