fullerenes

464 Annu. Rep. Prog. Chem., Sect. A: Inorg. Chem., 2012, 108, 464–477

This journal is © The Royal Society of Chemistry 2012

Cite this: Annu. Rep. Prog. Chem., Sect. A: Inorg. Chem., 2012, 108, 464–477

Fullerenes

Adam D. DarwishDOI: 10.1039/c2ic90017c

This chapter reviews the literature reported during 2011 on fullerene chemistryincluding fullerene production and properties, organic and organometallicchemistry, endohedral derivatives and advanced materials as well as theoreticalstudies and possible applications of fullerene and its derivatives.

Highlights

A facile preparation of highly water-soluble derivatives C70[p-C6H4(CH2)nCOOH]8(n= 2, 3) has been reported. The synthesised fullerene derivatives demonstrated low

toxicity in vitro and in vivo in combination with the pronounced antiviral activity

observed against HIV and influenza virus.1

1 Production, separation and properties of fullerenes

The methods for fullerene synthesis and the novel cage geometries that have been

retrieved and characterised to date were reviewed. The most recent theoretical

studies on formation mechanisms, stability, and reactivity of empty and endohedral

fullerenes have also been reviewed.2

Advances in the production, separation and characterisation of various fullerenes

were presented, including hollow fullerenes, endohedral fullerenes, exohedral derivatives

of fullerenes and azafullerenes.3 All four well known carbon forms, diamond, graphitic,

fullerenic and amorphous particles were detected at the same position in a candle flame

using ultrathin porous anodic aluminium oxide foils to capture soot particles in a

candle flame.4 The life cycle embodied energy of C60 and C70 fullerenes has been

quantified, including the relative contributions from synthesis, separation, purification,

and functionalisation processes.5 Three common extraction methods were used to

quantify C60 and qualitatively detect C70 in five commercial cosmetic samples.6 The

synthesis and characterisation of a new family of deconvoluted fullerene derivatives

have been described.7

Binary solid solutions of C60–C70 were prepared via volatilisation of solutions of

C60 and C70 in toluene as the solvent.8 Heptagon-containing fullerene C68 which is

captured as C68Cl6 from a carbon arc plasma in situ was reported.9

Department of Chemistry, School of Life Sciences, University of Sussex, Falmer,Brighton BN1 9QJ, UK. E-mail: [email protected]; Fax: +01273606196

Annual Reports A Dynamic Article Links

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http://dx.doi.org/10.1039/C2IC90017C

http://pubs.rsc.org/en/journals/journal/IC

http://pubs.rsc.org/en/journals/journal/IC?issueid=IC012108

Annu. Rep. Prog. Chem., Sect. A: Inorg. Chem., 2012, 108, 464–477 465


Samples of amorphous fullerites C70 have been obtained by grinding in a ball mill.

The structure of the samples has been investigated by neutron and XRD. Possible

structural versions of the high-temperature amorphous phase were discussed.10

A systematic survey on both classical and non-classical isomers of fullerene C46 to

probe their structures and stability were presented.11

Three isomers of C90 have now been isolated and crystallographically characterised.12

Electronic structure and stability of all nine IPR isomers of fullerene C8213 and all

nineteen IPR isomers of fullerene C8614 were investigated by DFT methods.

A high dispersion of pristine C60 with a small dispersion size, excellent stability

and high concentration in aqueous solution was achieved in the presence of BSA as a

biocompatible solubiliser by means of the unfolding mechanism.15

The solubilisation of fullerene using nine different solubility enhancers was

investigated and evaluated its antioxidant activity in biorelevant media.16

Polythermal solubility of individual light fullerenes (C60, C70) and industrial fullerene

mixture (60%C60, 39%C70, 1%C76–90) in some essential oils17 and in oleic, linoleic and

linolenic acids18,19 was investigated. Temperature dependencies of solubility were

presented and characterised. The degradation and transformation of C60 aqueous

suspensions exposed to simulated sunlight were studied. The results demonstrates that

C60 is not stable in the environment and that the breakdown products should be

considered when evaluating the environmental impact of C60.20 The first detailed

analysis of the UV–Vis spectroscopic properties of nC60 produced via extended mixing

in water in the absence of any organic solvents or surfactants was provided.21

Structure, mechanical and electrical properties of thin films prepared by means of

co-deposition of C60 and titanium were studied. The results show the potential

applicability of Ti-C60 films as electrotechnical materials and coatings.22

The influence of C60 on flow electrification of mineral insulating oil was examined.

The studies show that the change in flow electrification varies with C60 concentration.23

The pulmonary inflammation pattern after exposure to C60 via both intratracheal

and inhalation instillation was found to be slight and transient.24 An initial hazard

assessment, including a review of the available toxicity information of the effects of

C60 on the lungs was presented.25

The resistance of five different fullerenes (C60, C70, C76/78 mix, and C84) to

chemothermal oxidation at 375 1C was tested.26

UV-Vis spectrum of the neutral and ionised C84 isolated in inert neon matrices at

low temperature was presented. The results demonstrate that there is a strong need

for gas-phase spectra of large fullerenes.27

2 Chemistry of the fullerenes

2.1 Organic chemistry

2.1.1 Addition reactions. The formation of covalent C60 monolayers through

[4+2] Diels-Alder cycloaddition between C60 and anthracene monolayers grafted

onto a silicon oxide surface was investigated by ellipsometry, fluorescence and by

atomic force microscopy.28 Exohedral functionalisation of C60 fullerenes, the

random bisaddition, the regioselective bisaddition by using covalent templates, the

properties of fullerene adducts, and the applications into interlocked molecules have

been investigated.29 The kinetics and regiochemistry of the Diels-Alder reaction of

variously substituted fulleroids and methanofullerene with five different dienes have

been investigated in comparison with the analogous reaction of C60. The relative

reactivity of the fulleroids vs. C60 was found to be dependent on the identity of the

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diene as well as the fulleroid substituent.30 Pyridyl and phenyl-containing dihydrofuran-

fused C60 derivatives were prepared by the base-catalysed orMn(OAc)3-mediated [3+2]

cycloaddition reactions of C60 with the corresponding b-keto esters in high yields. All

the new compounds were characterised by elemental analysis and various spectroscopic

methods.31 C60-fused tetrahydronaphthalene and indane derivatives were obtained from

the reaction of C60 with malonates and cyanoacetates substituted with an aryl or a

benzyl group mediated by Mn(OAc)3 in combination with AlCl3 via a radical addition

and aryl annulation sequence.32 Various C60 and C70 fullerene-based electron acceptor

materials for organic photovoltaic applications were prepared via [3+2] and [4+2]

cycloadditions using a continuous flow approach.33

2.1.2 Alkylation and arylation. The monoalkylated C60 was obtained in high yield

by co-catalysed hydroalkylation of C60 with reactive alkyl bromides in the presence of

Mn reductant and H2O at ambient temperature.34 A new FeCl3-mediated polyarylation

of C60, which produces in quantitative conversion a polyarylated fullerene mixture

containing C60(C6H4Cl)5Cl in reasonable yield and polyarylated product having more

than five aryl groups has been described.35 A concise synthesis of 1,4-diaryl-C60 fullerene

adducts by a unique combination of AlCl3-mediated Friedel–Crafts reaction and a Cu(I)

mediated dehydrogenation has been developed.36

A new three-stage synthesis involving addition of a silylmethylmagnesium chloride

to C60 and C70 fullerene and oxidation of the anionic intermediate with CuCl2 afforded

the methano-C60 and methano-C70 fullerenes in high yield.37

Novel (PhCH2)HC70 regioisomers with the addends in both the equatorial and

polar regions of C70 have been prepared via the reaction of C702– with benzyl

bromide and H2O. Computational calculations have been carried out to rationalise

the formation of the C70HR regioisomers.38 Two exohedral C70 derivatives,

C70(C14H10) and C70(C5H6) have been chromatographically separated from flame

soot of the acetylene-benzene combustion and characterised by various spectro-

scopic techniques in combination with theoretical simulation.39

2.1.3 Hydrogenation. Hydrofullerenes have been produced experimentally with

variable content of hydrogen. The optimum regime of C60 hydrogenation has been

determined resulting in the full formation of the hydrogenated fullerene molecule

C60H60. The mechanism for the definition of hydrogenation degree has been

proposed.40 Kinetics and pathways of C60 reaction with hydrogen gas were studied

in a broad temperature interval and over extended periods of time. Hydrogenation

products were studied by XRD, mass spectrometry, liquid chromatography, and

elemental analysis. Hydrogenation pathways from C60H18 up to C60H56 and possible

mechanisms of hydrogenation-induced fragmentation of fullerenes were discussed.41

Hydrogenation from C60 to C60H60 was studied by an unrestricted broken spin

symmetry Hartree-Fock approach implemented in semiempirical codes based on the

AM1 technique. The calculations focused on the successive addition of hydrogen

molecules to the fullerene cage. The results obtained were analysed from energy,

symmetry, and composition perspectives.42 Mono-hydrogenation effect on the

properties of fullerenes C60 and C70 was investigated by DFT. One isomer of

C60H and five isomers of C70H were examined, comparing with C60 and C70. These

results show that the addition of atomic hydrogen strongly affects the properties of

fullerenes and that mono hydrogenation can be used as efficient method to modify

these properties.43

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2.1.4 Polymerisation. Manganese(III) acetate mediated radical reaction of C60

with phosphonate esters in chlorobenzene afforded singly-bonded fullerene dimers of

which the individual meso and racemic isomers could be unexpectedly separated and

their identities established by XRD.44

The formation of singly bonded PhCH2C60–C60CH2Ph dimers, which consist of

the meso and racemic regioisomers was achieved via electroreduction and electro-

oxidation of 1,2-(PhCH2)HC60.45

The endohedral nitrogen fullerene dimer N@C140H24O12 was synthesised and

isolated in a two-step synthesis via the respective monomer. The products were

characterised by a range of analytical tools, and their structures were confirmed by

MALDI mass spectrometry, UV-Vis, FT-IR, 1H NMR, and 13C NMR spectro-

scopy.46

Cyclic nickel and free-base porphyrin dimers including C70 fullerene both in

solution and in crystals were reported.47

2.1.5 Fullerene derivatives containing halogens. Starlike poly(vinylidene fluoride)

with a fullerene core was synthesised in high yield by reaction of azide-terminated

PVDF with C60 molecules at 160 1C under microwave irradiation in 90 minute.48

Perfluoroalkylfullerene C60(C2F5)5H, which is predicted to be the first gas-phase

fullerene superacid was synthesised by the reaction between C60Cl6 in toluene and

C2F5Li in diethyl ether at low-temperature and characterised using various spectro-

scopic techniques.49 The ‘‘capturing’’ of perchlorinated pyracylene (C14Cl8) by C60

fullerene formed in situ during radio-frequency furnace synthesis in a chlorine-

containing atmosphere was reported. It was suggested that C60C14Cl8 forms by reaction of

C60 with reactive partially chlorinated C14 clusters exhibiting pyracylene connectivity and

subsequent stabilisation by chlorine addition.50 The new C60(i-C3F7)2,4,6 and C70(i-C3F7)2,4isomers were synthesised using i-C3F7I in a continuous flow apparatus at high temperature

or at room temperature under UV irradiation. These perfluoroisopropyl derivatives were

characterised by spectroscopic methods, XRD, CV and DFT, which provide compelling

evidence that they are superior electron acceptors than trifluoromethylfullerenes.51

The Bingel reaction of the Cs isomer of C70(CF3)8 has been found to yield two

C70(CF3)8[C(CO2Et)2] monoadducts and one C70(CF3)8[C(CO2Et)2]2 bisadduct as its

major products. Dimerisation of these monomeric compounds as well as the parent

Cs–C70(CF3)8 via an equatorial [5,6]-bond occurs upon their crystallisation.52 The first

example of a non-IPR hollow fullerene that is more stable than the IPR isomer has

been reported for C72Cl4C2v. The structure has been determined by X-ray analyses.53

It was found that, in addition to the known C76Cl18 and C76Cl34 a number of

intermediate chlorides C76Cl18–C76Cl28 and C76Cl30–C76Cl34 were formed during the

chlorination of the C76 fullerene under various conditions.54

Two isomers of Sc3N@C80(CF3)14 and Sc3N@C80(CF3)16 were obtained by

trifluoromethylated of Sc3N@C80 with CF3I at 4000C. The isomers were separated

by HPLC and investigated by XRD.55

A series of C90Cln compounds with n ranging from 22 to 32 resulted from the

chlorination of pure C90 with VCl4 or SbCl5 in ampoules at 290–310 1C. Single-

crystal X-ray crystallography with the use of synchrotron radiation resulted in

structure elucidation of seven C90Cln compounds containing six different IPR C90

cages.56

The synthesis and characterisation of five members of azafullerenes C59N(CF3)nshowed a profound effect of the cage nitrogen atom on the addition patterns.57

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2.1.6 Fullerene derivatives containing nitrogen. The recent progress in the synthesis of

different types of porphyrin-fullerene complexes, including the synthesis and application

prospects of covalently linked porphyrin-fullerene compounds, and the existing problems

in synthetic methods and further prospects for this field has been reviewed.58 The

remarkable electrochemical and photophysical properties of 2-pyrazolino-C60 fullerenes

resulting from cycloaddition of nitrile imines to C60 were reviewed.59

Novel C60 fullerenes derivatives having an azetidinimine framework were synthe-

sised using a photochemical reaction with formamidines. They were characterised

using spectroscopic methods revealing a unique four-membered ring containing a

nitrogen atom.60 A new C60-fulleropyrrolidine tricarbonylchromium complex was

successfully prepared and characterised spectroscopically as well as by electro-

chemical and IR spectroelectrochemical methods.61 It was demonstrated that the

reaction of the bisaziridines with fullerene C60 can be used for selective preparation

of both monoadducts and bisadducts in moderate to good yields with a high degree

of stereocontrol.62 It was found that the reaction between a bulky N-heterocylic

carbene and C60 or C70 leads to the formation of a thermally stable zwitterionic

Lewis acid–base adduct that is connected via a C–C single bond.63 A new ethynyl-

bridged C60 derivative bearing a diketopyrrolopyrrole moiety has been synthesised

by ethynylation reaction and characterised using spectroscopic techniques.64

A series of C60/C70 fullerene derivatives containing different spirobifluorene and

triphenyl imidazole were synthesised and confirmed by spectroscopic techniques.

Their optical limiting properties were investigated by nanosecond and femtosecond

laser systems.65 The one-step synthesis of highly C70 selective shape-persistent organic

rectangular prismatic cages consisting of only aromatic moieties in its backbone

structure via Mo(VI) carbyne catalysed alkyne metathesis from tetrasubstituted

porphyrin monomers in decent yields was described.66

2.1.7 Fullerene derivatives containing oxygen. The assembly behaviour of

C60(OH)8 in aqueous solution and on surfaces with different hydrophobicity was

studied.67 Novel nanocomposite films of polycarbonate with polyhydroxylated

fullerenes C60(OH)12 and C60(OH)36 were prepared. The optical, thermal, and

mechanical properties of the composites were measured.68 Based on molecular

dynamics simulations, C60(OH)24 can form hydrogen bonds with the surrounding

water molecules which can increase dramatically their hydration energy.69

Three new amphiphilic dendrofullerenes endowed with 4, 8, and 16 carboxylic

groups have been efficiently prepared by using a click chemistry methodology and

fully characterised by standard spectroscopic and analytical techniques. These

amphiphilic C60 fullerene derivatives aggregate forming micelles, nanorods, or

hollow vesicles depending on the concentration and on the solid substrate.70

It was demonstrated that it is possible to adorn C60 with crown ether rings and

then use them as recognition sites for dibenzylammonium cationic derivatives.71

The rearrangement reaction of oxazoline rings from [6,6]- to [5,6]-junction on C60

surface upon 1,4-addition of benzyl bromide has been explored by using CV and

stepwise addition of PhCH2Br and PhCD2Br. The results have extended the scope of

cyclic isomerisation reactions of organofullerenes.72

An open-cage fullerendione with a 12-membered orifice has been prepared

through silane/borane-induced hemiketal formation and subsequent oxidation of a

vicinal fullerendiol. The structure of the open-cage fullerendione was confirmed by

single-crystal XRD.73

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The formation of lactone-containing open-cage C60 fullerene and detailed further

reactions of the lactone moiety leading to hole-expanded fullerene derivatives has

been reported. The products were characterised by spectroscopic and XRD data.74

Isomerically pure C60 fullerene multiadducts containing five amino groups together

with one hydroxyl, one epoxy and three ether moieties were synthesised via further

amination of aminoketal-C60 with pyrrolidine. The structure has been determined by

spectroscopic and XRD data.75

A one-pot cascade procedure has been developed to prepare an 18-membered

open-cage fullerene derivative mediated by C60 fullerene-mixed peroxide.76

A mixture of stable derivatives of C60/C70 fullerenes containing ether/diketone

functional groups were obtained during the destruction of fullerenes upon annealing

in air. The results were confirmed by IR and UV spectroscopy.77

2.2 Organometallic chemistry

The synthesis and crystallographic characterisation of the pentaaryl-C60 fulleride

tricyclohexylphosphine and triphenylphosphine complexes of gold(I), silver(I), and

copper(I) have been achieved.78 It was demonstrated that the cationic fullerene generated

through the oxidation of a fullerene radical or a fullerene anion with a Cu(II) salt is useful

for the synthesis of noncyclic 1,2-di(organo)-C60 fullerene derivatives that can be

selectively prepared through intramolecular 1,4-aryl migration of an aryl group from a

silicon atom to the fullerene core.79 The borane-protected dihydridodiphosphinofullerene

1,2,4,15-(PPh2�BH3)2(H)2C60 has been prepared by nucleophilic addition of two

[H3B�PPh2]– anions to C60 at low temperature, followed by protonation with

aqueous HCl.80 A facile synthesis of rhenium, iridium and platinum compounds

of isoxazoline-C60 fullerenes bearing covalently linked chelating moieties such as

pyridine and phenol that enhance the coordinative capability of the nitrogen in the

isoxazoline ring has been described.81 The synthesis and full characterisation of

novel four-membered aromatic systems consisting of planar cobalt trichalcogenide

compounds protected inside a bowl-shaped confined space of pentaaryl-C60 fullerene

has been explored.82

Pd and Ru–C60 compounds were synthesised by doping 1 wt% of each metal

on the pure C60 fullerene followed by hydrogen sorption measurements at 300 bar

and 298 K. The resulting complexes were characterised with TEM, XRD and

Raman spectroscopic analyses.83 The manganese (III) acetate dihydrate mediated

reaction of C60 with phosphonate esters or phosphine oxide in chlorobenzene

under three different conditions afforded three different types of phosphorylated

fullerenes that is, singly bonded fullerene dimers, hydrofullerenes, and acetoxylated

fullerenes.84

A series of zinc(II)porphyrins and fullerenes linked through a central triazole

moiety (ZnP–Tri–C60) conjugates have been synthesised using electron donor and

acceptor fragments containing terminal alkyne and azide functionality. The photophysical

properties of these conjugates were discussed.85 The formation of thermodynamically

stable inclusion complexes between two macrocyclic zinc bisporphyrins receptors, which

differ in the degree of the hydrocarbon linkers that connect their porphyrin units, and the

fullerenes C60 and C70 was described. The supramolecular structure of the two complexes

was determined by XRD.86

A method for the facile synthesis of C60Ar4(CH2SiMeR)H has been developed in

which a readily prepared anionic mono(silylmethyl) fullerene is subjected to reaction

conditions for organocopper-mediated multiple addition.87

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2.3 Advanced materials

The detailed synthesis and properties of oligofluorene modified C60 derivatives for

potential applications in organic electronic devices has been reported.88 Palladium-

catalysed syntheses of C60-isoquinolinones and C60-indolines were described and

their performances evaluated when incorporated with the conjugated polymer

P3HT.89 The effect of replacing PCBM by its multiadduct analogs bis-PCBM and

tris-PCBM in BHJ organic solar cells with P3HT was studied in terms of blend

film microstructure, photophysics, electron transport properties, and device

performance.90 The characterisation and evaluation in photovoltaic cells of novel

mono-o-quino-dimethane C60 and bis-o-quino-dimethane C60 yielding 4.1% and 5.2%

efficient devices in blends with P3HT respectively have been achieved.91 C60 has been

successfully derivatised by thermolysis with two new aryl azides in good yields. These were

characterised with spectroscopic techniques and then used to fabricate BHJ solar cells

with regioregular P3HT.92 A novel carbazole-group-containing fullerene derivative CBZ-

C60 was synthesised and characterised. The new C60 derivative showed good solubility in

common organic solvents. BHJ photovoltaic devices with the new C60 derivative and

P3HT were fabricated and evaluated.93 A porphyrin–C60 fullerene dyad was designed and

synthesised to serve as a new electron acceptor. The structure, morphology, and electro-

optical properties of this dyad were studied and it was evaluated as a BHJ material.94 A

new class of diphenylmethano-based C60 bis-adducts without incorporating aliphatic side

chains as a solubilising group have been rationally designed and successfully synthesised.95

Three types of fullerene C60-end-capped poly(4-diphenylaminostyrene) and poly-

(4-diphenylaminostyrene) blends were prepared to investigate their potential as

bipolar polymer semiconductors.96 Simple ways to form monolayers of C60 and

C60-ferrocene conjugated molecule on silicon oxide surfaces by using SAMs of C60

molecules bearing five carboxylic acids were suggested. The feasibility of these SAMs

as electrically active materials in field-effect transistors was investigated.97 A photo-

electric switch fabricated on indium tin oxide using a mixed SAM made of

C60(C6H4C6H4COOH)5Me and Fe[C70(C6H4C6H4COOH)3] Z5-C5Me5 generates a

bidirectional photocurrent of approximately +8 and �8 nA/cm2 upon irradiation at

340 and 490 nm, respectively.98

A series of soluble C70-derivatives (C70-PCBX) was synthesised by varying the alkyl

chain length of the adduct attached to the C70-polyhedron. The physico-chemical and

photovoltaic properties of the blend using the P3HT polymer as a donor were

evaluated.99 It was demonstrated that the PCE of BHJ plastic solar cells including

PCBX can be increased from 5 to 6.5% by incorporating an ultrathin conjugated

polyelectrolyte based on polythiophene backbones layer between the active layer and

the metal cathode.100 A new C70 derivative, biindene-C70 monoadduct (BC70MA), was

synthesised by [4+2] cycloaddition reaction between 1,10-biindene and C70 for

application as an acceptor in PSCs. The PCE of the PSC based on P3HT/BC70MA

reached 3%.101The detailed electronic structures of planar C70/CuPc bilayer and

mixed C70:CuPc BHJ have been studied by photoemission spectroscopy. The influence

of thermal annealing on the mixed C70:CuPc BHJ was also addressed.102

3 Endohedral fullerenes

The important chemical transformations of EMFs reported to date, including

disilylation, 1,3-dipolar cycloaddition with ylides, cyclopropanation with carbenes

and carbanions, cycloaddition with dienes and benzyne, radical reactions, and other

miscellaneous reactions, in addition to noncovalent interactions such as supramolecular

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complexation together with some applications were reviewed.103 The synthesis and

chemistry of endohedral fullerenes with particular focus on endohedral nitrogen fullerenes

such as N@C60 were reviewed.104

A novel method was developed to close the cage and encapsulate one water

molecule under high-pressure conditions. The structure of H2O@C60 was determined by

XRD analysis, along with its physical and spectroscopic properties.105 A highly stable

water soluble C60@Au core-shell structure was synthesised by direct encapsulation

giving rise to well-defined nanoshells with regular size and morphology.106

The synthesis of optically active bis-adducts of the non-IPR metallofullerene

La@C72 by the highly enantioselective cycloaddition reaction of N-metalated

azomethine ylides on a racemic mixture of La@C72(C6H3Cl2) was described.107

Two Yb@C76 isomers obtained experimentally have been found to possess the novel

non-IPR cages with one pair of adjacent pentagons.108 The electronic structure and

thermodynamic stability of dimetallofullerene Lu2@C76 have been investigated by means

of a combined quantum chemical and statistical thermodynamic method. It was found

that Lu2@C76 (Td), contains a single metal–metal bond between two Lu atoms.109

Isolation, characterisation, and detailed theoretical studies of Sc3NC@C78–C2

have been described. Various spectroscopic characterisations revealed the non-IPR

structure of Sc3NC@C78–C2.110 A new metallofullerene Y3N@C78–C2 was synthesised

and characterised. It was shown that Y3N@C78 has an unconventional C78–C2 cage

with two pairs of fused pentagons closely bonded with two yttrium atoms.111

The preparation, purification, and spectroscopic properties of a new dimetallic

EHF, Gd2@C79N were reported for the first time. Theoretical and experimental

results confirm that this molecule has an unusually high chemical stability and the

unpaired electron spin density is centered between the encapsulated Gd2 cluster.112

Highly stable (poly)perfluoroalky-lated metallic nitride cluster fullerenes,

Sc3N@C80(CF3)n (n = 2–16) were prepared in high-temperature reactions and

characterised by various spectroscopic, structural and electrochemical methods.113

Electrochemically generated Lu3N@Ih–C80 dianions react with the electrophile

PhCHBr2, to produce a methano derivative of Lu3N@Ih–C80(CHC6H5) with high

regioselectivity. The compound was characterised by various spectroscopic techniques.114

The regioselective cycloaddition of La2@Ih–C80 with tetracyanoethylene oxide, which

enabled the formation of the corresponding adduct having a tetracyanotetrahydrofuran

moiety were described. XRD analysis revealed that the cycloaddition took place as a [5,6]

addition.115 The synthesis and charge-transfer chemistry of two stable electron donor-

acceptor conjugates; La2@Ih–C80–ZnP and Sc3N@Ih–C80–ZnP was presented.116

A summary of the recent progress of chemical functionalisation and supramole-

cular chemistry of M@C82 was reviewed.117 A Sc2C84 isomer which had been

assumed as Sc2@C84 was structurally determined using single crystal XRD to be

Sc2C2@Cs(6)-C82.118

Four isomers of Sm@C90 were obtained from carbon soot produced by electric

arc vaporisation of carbon rods doped with Sm2O3. Their individual structures were

determined by single-crystal XRD.119

Systematic and detailed computational investigations on the characterisation of

both IPR and non-IPR La3N@C92 were described.120

4 Applications of fullerene derivatives

A brief summary of recent achievements in some exciting applications of fullerene

derivatives have been reported.121

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The biological effects in vitro of two water soluble inclusions complexes C60/PVP

and C60/g-CD were studied. It was found that both the two inclusion complexes are

different compounds with similar but not identical spectra of biological action.122

Fullerene C60 included in PEG at a composing ratio of 1 : 350 w/w was examined for

anticancer effects upon PDT. It was found that the anticancer effects were dependent

on PEG-C60 concentrations and irradiation doses.123 PEG samples with different

terminal structures and molecular weights were covalently coupled to C60 and their

superoxide anion generation, in vitro or in vivo antitumor activity, and body

distribution was assessed for the effect of the photosensitiser used in PDT on the

tumor.124 In order to design a novel cytospecific photosensitiser for antitumor PDT,

C60 fullerene was chemically modified with pullulan, a water-soluble polysaccharide.

The effect of the molecular weight of pullulan and the modification manner to C60 on

the antitumor PDT of C60 modified with pullulan was evaluated.125 A water-soluble

covalently linked C60-porphyrin compound was reported to show enhanced DNA-

cleaving activity. The results suggest a new strategy of developing water-soluble

fullerene-porphyrin conjugates for their promising application in PDT.126

The neuroprotective action of hybrid structures based on C60 fullerene with

attached proline amino acid has been studied. It has been shown that all studied

compounds have antioxidant activity and decreased the concentration of malon-

dialdehyde in homogenates of the rat brain.127

Substantial evidence that administration of hydrated C60 fullerene, C60HyFn,

significantly reduces diabetes-induced oxidative stress and associated complications

such as testicular dysfunction and spermatogenic disruption have been presented for

the first time.128 The effects of magnesium-25 carrying porphyrin-C60 fullerene

nanoparticles that have the potential to prevent dorsal root ganglion neuron

degeneration and motor dysfunction symptomatically for diabetic neuropathy were

evaluated.129 The modification of Au(111) surfaces bearing pyrrolidino-C60 fullerene

derivatives led to bioactive materials displaying full biocompatibility and neuroprotective

actions in contrasting L-glutamate induced excitotoxicity.130 It was reported that aqueous

C60 fullerene suspensions prepared by the tetrahydofuran-water exchange method have

positive responses in two bacterial genotoxicity tests.131

Two conjugates of C60 and tuftsin, NH2–tuftsin–C60 and C60–tuftsin–COOH, by

covalently coupling C60 to the carboxyl or amino terminal of the tetrapeptide tuftsin,

were synthesised, characterised and their immunostimulating activities evaluated.132

The reversible hydrogen storage/release phenomena of lithium fulleride (LinC60)

were presented. The 7Li and 13C solid-state NMR analyses revealed that LiH and

C60Hn were formed at the hydrogen stored state, and LinC60 was formed at the

hydrogen released state.133 A mixed-valence cluster of cobalt(11) hexacyanoferrate

and fullerene C60-enzyme-based electrochemical glucose sensor was developed.134

The preparation and spectroscopic characterisation of the water soluble sodium

fullerenolate Na4[C60(OH)30] has been reported. It has been revealed for the first

time that sodium fullerenolate destroys amyloid fibrils of the Ab(1–42) peptide in the

brain and prevents their formation in in vitro experiments.135

A study performed on HT-29 human colon carcinoma cells exposed first to a

fullerene derivative C60(OH)20 and then to physiological copper ions showed that

C60(OH)20 suppressed cell damage as well as ROS production induced by copper.136

It has been shown that the highly hydroxylated fullerene derivatives; C60(OH)6-12,

C60(OH)32-34 .7H2O and C60(OH)44 .8H2O protects human keratinocytes from

UV-induced cell injuries together with the decreases in intracellular ROS generation

and DNA damages.137 It was reported thatC60(OH)24 produces a strong acute

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anti-inflammatory activity.138 The toxicity and inflammatory potential of three

fullerenols C60(OH)20, C60(OH)24, C60(OH)32 in human skin cells was assessed at

various concentrations.139 It has been found that the [Gd@C82(OH)22]n nanoparticle

is a potent activator of macrophages which may in part account for its potent anti-

tumor effect.140

List of Abbreviations

BHJ bulk heterojunctionBSA bovine serum albuminCuPc copper phthalocyanineCV cyclic voltammetryCyD gamma cyclodextrinDFT density functional theoryEHF dimetallic endohedral heterofullereneEMFs endohedral metallofullerenesFT-IR fourier transformer infraredHIV human immunodeficiency virusHPLC high performance liquid chromatographyIPR isolated pentagon ruleMALDI matrix assisted laser desorption ionizationNMR nuclear magnetic resonanceOPV oligophenylenevinylenePCBM [6,6]-phenyl-C61-butyric acid methyl esterPCBX ([6,6]-phenyl C71-butyric acid alkyl ester)PCE power conversion efficiencyPDT photodynamic therapyPEG polyethylene glycolP3HT poly(3-hexylthiophene)PSC polymer solar cellPVDF poly(vinylidene fluoride)PVP polyvinylpyrrolidoneROS reactive oxygen speciesSAMs self-assembled monolayersTEM transmission electron microscopyXRD X-ray diffractionXPS X-ray photoelectron spectroscopyUV-Vis ultra violet-visibleZnP zinc porphyrin

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