Abstract
Buckyballs represent a new and fascinating molecular allotropic form of carbon that has received a lot of attention by the chemical community during the last two decades. The unabating interest on this singular family of highly strained carbon spheres has allowed the establishing of the fundamental chemical reactivity of these carbon cages and, therefore, a huge variety of fullerene derivatives involving [60] and [70]fullerenes, higher fullerenes, and endohedral fullerenes have been prepared. Much less is known, however, of the chemistry of the uncommon non-IPR fullerenes which currently represent a scientific curiosity and which could pave the way to a range of new fullerenes. In this review on buckyballs we have mainly focused on the most recent and novel covalent chemistry of fullerenes involving metal catalysis and asymmetric synthesis, as well as on some of the most significant advances in supramolecular chemistry, namely H-bonded fullerene assemblies and the search for efficient concave receptors for the convex surface of fullerenes. Furthermore, we have also described the recent advances in the macromolecular chemistry of fullerenes, that is, those polymer molecules endowed with fullerenes which have been classified according to their chemical structures. This review is completed with the study of endohedral fullerenes, a new family of fullerenes in which the carbon cage of the fullerene contains a metal, molecule, or metal complex in the inner cavity. The presence of these species affords new fullerenes with completely different properties and chemical reactivity, thus opening a new avenue in which a more precise control of the photophysical and redox properties of fullerenes is possible. The use of fullerenes for organic electronics, namely in photovoltaic applications and molecular wires, complements the study and highlights the interest in these carbon allotropes for realistic practical applications. We have pointed out the so-called non-IPR fullerenes – those that do not follow the isolated pentagon rule – as the most intriguing class of fullerenes which, up to now, have only shown the tip of the huge iceberg behind the examples reported in the literature. The number of possible non-IPR carbon cages is almost infinite and the near future will show us whether they will become a reality.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Notes
- 1.
All through the article we will report binding constants as logarithms, and without an error interval, for simplicity. The reader can refer to the original publications for these data.
References
Kroto HW, Heath JR, O’Brien SC et al (1985) C60: buckminsterfullerene. Nature 318:162–163
Cami J, Bernard-Salas J, Peeters E et al (2010) Detection of C60 and C70 in a young planetary nebula. Science 329:1180–1182
Iijima S (1991) Helical microtubules of graphitic carbon. Nature 354:56–58
Iijima S, Ichihashi T (1993) Single-shell carbon nanotubes of 1-nm diameter. Nature 363:603–605
Bethune DS, Kiang CH, de Vries MS et al (1993) Cobalt-catalyzed growth of carbon nanotubes with single-atomic-layer walls. Nature 363:605–607
Novoselov KS, Geim AK, Morozov SV et al (2004) Electric field effect in atomically thin carbon films. Science 306:666–669
Delgado JL, Herranz MA, Martín N (2008) The nanoforms of carbon. J Mater Chem 18:1417–1426
Akasaka T, Nagase S (2002) Endofullerenes: a new family of carbon cluster. Kluwer, Dordrecht
Kroto HW (1997) Symmetry, space, stars, and C60. Angew Chem Int Ed 36:1578–1593
Smalley RE (1997) Discovering the fullerrenes. Angew Chem Int Ed 36:1594–1601
Curl RF (1997) Dawn of the fullerenes: conjecture and experiment. Angew Chem Int Ed 36:1566–1576
Martín N (2006) New challenges in fullerene chemistry. Chem Commun 2093–2104
Krätschmer W, Lamb LD, Fostiropoulos K et al (1990) Solid C60: a new form of carbon. Nature 347:354–358
Jones DEH (1966) Hollow molecules. New Sci 32:245
Chuvilin A, Kaiser U, Bichoutskaia E et al (2010) Direct transformation of graphene to fullerene. Nat Chem 2:450–453
Kroto HW (1987) The stability of the fullerenes Cn, with n = 24, 28, 32, 36, 50, 60 and 70. Nature 329:529–531
Haddon RC (1992) Electronic structure, conductivity, and superconductivity of alkali metal doped C60. Acc Chem Res 25:127–133
Hirsch A, Chen Z, Jiao H (2000) Spherical aromaticity in Ih symmetrical fullerenes: the 2(N + 1)2 rule. Angew Chem Int Ed 39:3915–3917
Guldi DM, Martín N (eds) (2002) Fullerenes: from synthesis to optoelectronic properties. Kluwer Academic, Dordrecht
Hirsch A, Brettreich M (2005) Fullerenes, chemistry and reactions. Wiley-VCH, Weinheim
Langa F, Nierengarten JF (eds) (2012) Fullerenes: principles and applications. Royal Society of Chemistry, Cambridge
Haddon RC, Brus LE, Raghavachari K (1986) Electronic structure and bonding in icosahedral carbon cluster (C60). Chem Phys Lett 125:459–464
Xie Q, Perez-Cordero E, Echegoyen L (1992) Electrochemical detection of C60 and C70: enhanced stability of fullerides in solution. J Am Chem Soc 114:3978–3980
Martin N, Altable M, Filippone S et al (2006) Thermal [2+2] intramolecular cycloadditions of fuller-1,6-enynes. Angew Chem Int Ed 45:1439–1442
Altable M, Filippone S, Martin-Domenech A et al (2006) Intramolecular ene reaction of 1,6-fullerenynes: a new synthesis of allenes. Org Lett 8:5959–5962
Li H, Risko C, Seo JH et al (2011) Fullerene–carbene Lewis acid–base adducts. J Am Chem Soc 133:12410–12413
Cozzi F, Powell WH, Thilgen C (2005) Numbering of fullerenes. Pure Appl Chem 77:843–923
Komatsu K, Murata Y, Takimoto N et al (1994) Synthesis and properties of the first acetylene derivatives of C60. J Org Chem 59:6101–6102
Nagashima H, Terasaki H, Kimura E et al (1994) Silylmethylations of C60 with Grignard reagents: selective synthesis of HC60CH2SiMe2Y and C60(CH2SiMe2Y)2 with selection of solvents. J Org Chem 59:1246–1248
Hirsch A, Soi A, Karfunhel HR (1992) Titration of C60: a method for the synthesis of organofullerenes. Angew Chem Int Ed 31:766–768
Sawamura M, Iikura H, Nakamura E (1996) The first pentahaptofullerene metal complexes. J Am Chem Soc 118:12850–12851
Matsuo Y, Nakamura E (2008) Selective multiaddition of organocopper reagents to fullerenes. Chem Rev 108:3016–3028
Martin N, Altable M, Filippone S et al. (2004) Highly efficient Pauson–Khand reaction with C60: regioselective synthesis of unprecedented cis-1 biscycloadducts. Chem Commun 1338–1339
Martín N, Altable M, Filippone S et al (2005) Regioselective intramolecular Pauson–Khand reactions of C60: an electrochemical study and theoretical underpinning. Chemistry 11:2716–2729
Nambo M, Noyori R, Itami K (2007) Rh-catalyzed arylation and alkenylation of C60 using organoboron compounds. J Am Chem Soc 129:8080–8081
Nambo M, Segawa Y, Wakamiya A et al (2011) Selective introduction of organic groups to C60 and C70 using organoboron compounds and rhodium catalyst: a new synthetic approach to organo(hydro)fullerenes. Chem Asian J 6:590–598
Lu S, Jin T, Bao M et al (2011) Cobalt-catalyzed hydroalkylation of [60]fullerene with active alkyl bromides: selective synthesis of monoalkylated fullerenes. J Am Chem Soc 133:12842–12848
Xiao Z, Matsuo Y, Nakamura E (2010) Copper-catalyzed formal [4+2] annulation between alkyne and fullerene bromide. J Am Chem Soc 132:12234–12236
Zhu B, Wang G-W (2009) Palladium-catalyzed heteroannulation of [60]fullerene with anilides via C–H bond activation. Org Lett 11:4334–4337
Thilgen C, Gosse I, Diederich F (2003) Chirality in fullerene chemistry. Top Stereochem 23:1–124
Thilgen C, Diederich F (2006) Structural aspects of fullerene chemistry: a journey through fullerene chirality. Chem Rev 106:5049–5135
Nishimura T (2004) Macromolecular helicity induction on a poly(phenylacetylene) with C2-symmetric chiral [60]fullerene-bisadducts. J Am Chem Soc 126:11711–11717
Friedman SH, Ganapathi PS, Rubin Y et al (1998) Optimizing the binding of fullerene inhibitors of the HIV-1 protease through predicted increases in hydrophobic desolvation. J Med Chem 41:2424–2429
Hizume Y, Tashiro K, Charvet R et al (2010) Chiroselective assembly of a chiral porphyrin–fullerene dyad: photoconductive nanofiber with a top-class ambipolar charge-carrier mobility. J Am Chem Soc 132:6628–6629
Filippone S, Maroto EE, Martín-Domenech A et al (2009) An efficient approach to chiral fullerene derivatives by catalytic enantioselective 1,3-dipolar cycloadditions. Nat Chem 1:578–582
Maroto EE, Filippone S, Martin-Domenech A et al (2012) Switching the stereoselectivity: (fullero)pyrrolidines “a la carte”. J Am Chem Soc 134:12936–12938
Maroto EE, de Cózar A, Filippone S et al (2011) Hierarchical selectivity in fullerenes: site-, regio-, diastereo-, and enantiocontrol of the 1,3-dipolar cycloaddition to C70. Angew Chem Int Ed 50:6060–6064
Sawai K, Takano Y, Izquierdo M et al (2011) Enantioselective synthesis of endohedral metallofullerenes. J Am Chem Soc 133:17746–17752
Bosi S, Da Ros T, Spalluto G et al (2003) Fullerene derivatives: an attractive tool for biological applications. Eur J Med Chem 38:913–923
Prato M, Martín N (eds) (2002) Special issue: Functionalised fullerenes. J Mater Chem 12:1931–2159
Manoharan M, de Proft F, Geerlings P (2000) Aromaticity interplay between quinodimethanes and C60 in Diels–Alder reactions: insights from a theoretical study. J Org Chem 65:6132–6137
Kräutler B, Maynollo J (1995) A highly symmetric sixfold cycloaddition product of fullerene C60. Angew Chem Int Ed Engl 34:87–88
Herranz MA, Martín N, Ramey J et al (2002) Thermally reversible C60-based donor–acceptor ensembles. Chem Commun 2002:2968–2969
Bingel C (1993) Cyclopropanierung von fullerenen. Chem Ber 126:1957–1959
Kessinger R, Crassous J, Herrmann A et al (1998) Preparation of enantiomerically pure C76 with a general electrochemical method for the removal of di(alkoxycarbonyl)methano bridges from methanofullerenes: the retro-Bingel reaction. Angew Chem Int Ed 37:1919–1922
Kessinger R, Fender NS, Echegoyen LE et al (2000) Selective electrolytic removal of bis(alkoxycarbonyl)methano addends from C60 bis-adducts and electrochemical stability of C70 derivatives. Chemistry 6:2184–2192
Moonen NNP, Thilgen C, Echegoyen L et al (2000) The chemical retro-Bingel reaction: selective removal of bis(alkoxycarbonyl)methano addends from C60 and C70 with amalgamated magnesium. Chem Commun 5:335–336
Prato M, Maggini M (1998) Fulleropyrrolidines: a family of full-fledged fullerene derivatives. Acc Chem Res 31:519–526
Martín N, Altable M, Filippone S et al (2006) Retro-cycloaddition reaction of pyrrolidinofullerenes. Angew Chem Int Ed 45:110–114
Brunetti FG, Herrero MA, Muñoz JM et al (2007) Reversible microwave-assisted cycloaddition of aziridines to carbon nanotubes. J Am Chem Soc 129:14580–14581
Guryanov I, Montellano Lopez A, Carraro M et al (2009) Metal-free, retro-cycloaddition of fulleropyrrolidines in ionic liquids under microwave irradiation. Chem Commun 3940–3942
Filippone S, Izquierdo Barroso M, Martín-Domenech A et al (2008) On the mechanism of the thermal retrocycloaddition of pyrrolidinofullerenes (retro-Prato reaction). Chemistry 14:5198–5206
Lukoyanova O, Cardona CM, Altable M et al (2006) Selective electrochemical retro-cycloaddition reaction of pyrrolidinofullerenes. Angew Chem Int Ed 45:7430–7433
Martín N, Altable M, Filippone S et al (2007) Highly efficient retro-cycloaddition reaction of isoxazolino[4,5:1,2][60]- and -[70]fullerenes. J Org Chem 72:3840–3846
Delgado JL, Oswald F, Cardinali F et al (2008) On the thermal stability of [60]fullerene cycloadducts: retro-cycloaddition reaction of 2-pyrazolino[4,5:1,2][60]-fullerenes. J Org Chem 73:3184–3188
Olah GA, Bucsi I, Lambert C et al (1991) Polyarenefullerenes, C60(H-Ar)n, obtained by acid-catalyzed fullerenation of aromatics. J Am Chem Soc 113:9387–9388
Giacalone F, Martín N (2006) Fullerene polymers: synthesis and properties. Chem Rev 106:5136–5190
Giacalone F, Martín N (eds) (2009) Fullerene polymers: synthesis, properties and applications. Wiley VCH, Weinheim
Giacalone F, Martín N (2010) New concepts and applications in the macromolecular chemistry of fullerenes. Adv Mater 22:4220–4248
Special issue on polymeric fullerenes (1997) Appl Phys A: Mater Sci Process 64:223–330
Sundqvist B (1999) Fullerenes under high pressures. Adv Phys 48:1
Rao AM, Zhou P, Wang K-A et al (1993) Photo-induced polymerization of solid C60 films. Science 259:955–957
Iwasa Y, Arima T, Fleming RM et al (1994) New phases of C60 synthesized at high-pressure. Science 264:1570–1572
Takahashi N, Dock H, Matsuzawa N et al (1993) Plasma‐polymerized C60/C70 mixture films: electric conductivity and structure. J Appl Phys 74:5790–5798
Nuñez-Regueiro M, Marques L, Hodeau JL et al (1995) Polymerized fullerite structures. Phys Rev Lett 74:278–281
Rao AM, Eklund PC, Venkateswaran UD et al (1997) Properties of C60 polymerized under high pressure and temperature. Appl Phys A: Mater Sci Process 64:231–2239
Fedurco M, Costa DA, Balch AL et al (1995) Electrochemical synthesis of a redox-active polymer based on buckminsterfullerene epoxide. Angew Chem Int Ed Engl 34:194–196
Winkler K, Costa DA, Balch AL et al (1995) A study of fullerene epoxide electroreduction and electropolymerization processes. J Phys Chem 99:17431–17436
Liu B, Bunker CE, Sun T-P (1996) Preparation and characterization of soluble pendant [60]fullerene-polystyrene polymers. Chem Commun 1241–1242
Stalmach U, de Boer B, Videlot C et al (2000) Semiconducting diblock copolymers synthesized by means of controlled radical polymerization techniques. J Am Chem Soc 122:5464–5472
Zheng JW, Goh SH, Lee SY (2000) Miscibility of C60-containing poly(methyl methacrylate)/poly(vinylidene fluoride) blends. J Appl Polym Sci 75:1393–1396
Wang C, Tao Z, Yang W et al (2001) Synthesis and photoconductivity study of C60-containing styrene/acrylamide copolymers. Macromol Rapid Commun 22:98–103
Gutiérrez-Nava M, Masson P, Nierengarten J-F (2003) Synthesis of copolymers alternating oligophenylenevinylene subunits and fullerene moieties. Tetrahedron Lett 44:4487–4490
Vitalini D, Mineo P, Iudicelli V et al (2000) Preparation of functionalized copolymers by thermal processes: porphyrination and fullerenation of a commercial polycarbonate. Macromolecules 33:7300–7309
Kraus A, Müllen K (1999) [60]Fullerene-containing poly(dimethylsiloxane)s: easy access to soluble polymers with high fullerene content. Macromolecules 32:4214–4219
Ungurenasu C, Pienteala M (2007) Syntheses and characterization of water-soluble C60–curdlan sulfates for biological applications. J Polym Sci Part A: Polym Chem 45:3124–3128
Cravino A, Sariciftci NS (2002) Double-cable polymers for fullerene based organic optoelectronic applications. J Mater Chem 12:1931–1943
Cravino A, Sariciftci NS (2003) Organic electronics: molecules as bipolar conductors. Nat Mater 2:360–361
Kawase T (2012) Receptors for pristine fullerenes based on concave-convex π-π interactions. In: Martín N, Nierengarten J-F (eds) Supramolecular chemistry of fullerenes and carbon nanotubes. Wiley-VCH, Weinheim, pp 55–78 (Chap. 3)
Martín N, Nierengarten J-F (2012) Supramolecular chemistry of fullerenes and carbon nanotubes. Wiley-VCH, Weinheim
Sterescu DM, Stamatialis DF, Mendes E, Wibbenhorst M, Wessling M (2006) Fullerene-modified poly(2,6-dimethyl-1,4-phenylene oxide) gas separation membranes: why binding is better than dispersing. Macromolecules 39:9234–9242
Vinogradova LV, Polotskaya GA, Shevtsova AA et al (2009) Gas-separating properties of membranes based on star-shaped fullerene (C60)-containing polystyrenes. Polym Sci Ser A 51:209–215
Wang H, DeSousa R, Gasa J et al (2007) Fabrication of new fullerene composite materials and their application in proton exchange membrane fuel cells. J Membr Sci 289:277–283
Chen X, Gholamkhass B, Han X et al (2007) Polythiophene-graft-styrene and polythiophene-graft-(styrene-graft-C60) copolymers. Macromol Rapid Commun 28:1792–1797
Nanjo M, Cyr PW, Liu K et al (2008) Donor–acceptor C60-containing polyferrocenylsilanes: synthesis, characterization, and applications in photodiode devices. Adv Funct Mater 18:470–477
Ling Q-D, Lim S-L, Song Y et al (2007) Nonvolatile polymer memory device based on bistable electrical switching in a thin film of poly(N-vinylcarbazole) with covalently bonded C60. Langmuir 23:312–319
Tutt LW, Kost A (1992) Optical limiting performance of C60 and C70 solutions. Nature 356:225–226
Cha M, Sariciftci NS, Heeger AJ et al (1995) Enhanced nonlinear absorption and optical limiting in semiconducting polymer/methanofullerene charge transfer films. Appl Phys Lett 67:3850–3852
Maggini M, Scorrano G, Prato M et al (1995) C60 derivatives embedded in sol–gel silica films. Adv Mater 7:404–406
Bunker CE, Lawson GE, Sun YP (1995) Fullerene-styrene random copolymers. Novel optical properties. Macromolecules 28:3744–3746
Kojima Y, Matsuoka T, Takahashi H et al (1995) Optical limiting property of polystyrene-bound C60. Macromolecules 28:8868–8869
Lu Z, Goh SH, Lee SY et al (1999) Synthesis, characterization and nonlinear optical properties of copolymers of benzylaminofullerene with methyl methacrylate or ethyl methacrylate. Polymer 40:2863–2867
Sun YP, Riggs JE (1997) Non-linear absorptions in pendant [60]fullerene–polystyrene polymers. J Chem Soc Faraday Trans 93:1965–1969
Tang BZ, Xu HY, Lam JWY et al (2000) C60-containing poly(1-phenyl-1-alkynes): synthesis, light emission, and optical limiting. Chem Mater 12:1446–1449
Li FY, Li YL, Guo ZX et al (2000) Synthesis and optical limiting properties of polycarbonates containing fullerene derivative. J Phys Chem Solids 61:1101–1103
Celli A, Marchese P, Vannini M et al (2011) Synthesis of novel fullerene-functionalized polysulfones for optical limiting applications. React Funct Polym 71:641–647
Mroz P, Tegos GP, Gali H et al (2007) Photodynamic therapy with fullerenes. Photochem Photobiol Sci 6:1139–1149
Liu Y, Wang H, Liang P et al (2004) Water-soluble supramolecular fullerene assembly mediated by metallobridged β-cyclodextrins. Angew Chem Int Ed 43:2690–2694
Samal S, Choi B-J, Geckeler KE (2001) DNA-cleavage by fullerene-based synzymes. Macromol Biosci 1:329–331
Liu J, Ohta S, Sonoda A et al (2007) Preparation of PEG-conjugated fullerene containing Gd3+ ions for photodynamic therapy. J Control Release 117:104–110
Stoilova O, Jérôme C, Detrembleur C et al (2007) C60-containing nanostructured polymeric materials with potential biomedical applications. Polymer 48:1835–1843
Drees M, Hoppe H, Winder C et al (2005) Stabilization of the nanomorphology of polymer–fullerene “bulk heterojunction” blends using a novel polymerizable fullerene derivative. J Mater Chem 15:5158–5163
Sivula K, Ball ZT, Watanabe N et al (2006) Amphiphilic diblock copolymer compatibilizers and their effect on the morphology and performance of polythiophene:fullerene solar cells. Adv Mater 18:206–210
Yang C, Lee JK, Heeger AJ et al (2009) Well-defined donor–acceptor rod–coil diblock copolymers based on P3HT containing C60: the morphology and role as a surfactant in bulk-heterojunction solar cells. J Mater Chem 19:5416–5423
Hsieh C-H, Cheng Y-J, Li P-J et al (2010) Highly efficient and stable inverted polymer solar cells integrated with a cross-linked fullerene material as an interlayer. J Am Chem Soc 132:4887–4893
Cheng Y-J, Hsieh C-H, He Y et al (2010) Combination of indene-C60 bis-adduct and cross-linked fullerene interlayer leading to highly efficient inverted polymer solar cells. J Am Chem Soc 132:17381–17383
Jeffery GA (1997) An introduction to hydrogen bonding. Oxford University Press, Oxford
Collins AF, Critchley C (2005) Artificial photosynthesis: from basic biology to industrial applications. Wiley, Weinheim
Delgado JL, Bouit PA, Filippone S et al (2010) Organic photovoltaics: a chemical approach. Chem Commun 46:4853–4865
Pinzón JR, Villalta-Cerdas A, Echegoyen L (2012) Fullerenes, carbon nanotubes, and graphene for molecular electronics. Top Curr Chem 312:127–174
Diederich F, Echegoyen L, Gómez-López M et al (1999) The self-assembly of fullerene-containing [2]pseudorotaxanes: formation of a supramolecular C60 dimer. J Chem Soc Perkin Trans 2:1577–1586
Rispens MT, Sánchez L, Knol J et al (2001) Supramolecular organization of fullerenes by quadruple hydrogen bonding. Chem Commun 161–162
González JJ, González S, Priego E et al (2001) A new approach to supramolecular C60-dimers based in quadruple hydrogen bonding. Chem Commun 163–164
Da Ros T, Guldi DM, Morales AF et al (2003) Hydrogen bond-assembled fullerene molecular shuttle. Org Lett 5:689–691
Mateo-Alonso A, Fioravanti G, Marcaccio M et al (2006) Reverse shuttling in a fullerene-stoppered rotaxane. Org Lett 8:5173–5176
Mateo-Alonso A, Brough P, Prato M (2007) Stabilization of fulleropyrrolidine N-oxides through intrarotaxane hydrogen bonding. Chem Commun 1412–1414
Mateo-Alonso A, Fioravanti G, Marcaccio M et al (2007) An electrochemically driven molecular shuttle controlled and monitored by C60. Chem Commun 1945–1947
Scarel F, Valenti G, Gaikwad S et al (2012) A molecular shuttle driven by fullerene radical-anion recognition. Chemistry 44:14063–14068
Guldi DM, Ramey J, Martínez-Díaz MV et al (2002) Reversible zinc phthalocyanine fullerene ensembles. Chem Commun 2774–2775
Sánchez L, Sierra M, Martín N et al (2006) Exceptionally strong electronic communication through hydrogen bonds in porphyrin–C60 pairs. Angew Chem Int Ed 45:4637–4641
Sessler JL, Jayawickramarajah J, Gouloumis A et al (2005) Synthesis and photophysics of a porphyrin-fullerene dyad assembled through Watson–Crick hydrogen bonding. Chem Commun 1892–1894
Torres T, Gouloumis A, Sánchez-García D et al (2007) Photophysical characterization of a cytidine-guanosine tethered phthalocyanine-fullerene dyad. Chem Commun 292–294
Wessendorf F, Gnichwitz J-F, Sarova GH et al (2007) Implementation of a Hamilton-receptor-based hydrogen-bonding motif toward a new electron donor-acceptor prototype: electron versus energy transfer. J Am Chem Soc 129:16057–16071
Maurer K, Grimm B, Wessendorf F et al (2010) Self-assembling depsipeptide dendrimers and dendritic fullerenes with new cis- and trans-symmetric Hamilton receptor functionalized Zn–porphyrins: synthesis, photophysical properties and cooperativity phenomena. Eur J Org Chem 5010–5029
Grimm B, Schornbaum J, Jasch H et al (2012) Step-by-step self-assembled hybrids that feature control over energy and charge transfer. Proc Natl Acad Sci U S A 109:15565–15571
Santos J, Grimm B, Illescas BM et al (2008) Cooperativity between π-π and H-bonding interactions – a supramolecular complex formed by C60 and exTTF. Chem Commun 5993–5995
Huang C-H, McClenaghan ND, Kuhn A et al (2005) Enhanced photovoltaic response in hydrogen-bonded all-organic devices. Org Lett 7:3409–3412
Chu C-C, Raffy G, Ray D et al (2010) Self-assembly of supramolecular fullerene ribbons via hydrogen-bonding interactions and their impact on fullerene electronic interactions and charge carrier mobility. J Am Chem Soc 132:12717–12723
Pérez EM, Martín N (2008) Curves ahead: molecular receptors for fullerenes based on concave-convex complementarity. Chem Soc Rev 37:1512–1519
Tashiro K, Aida T (2007) Metalloporphyrin hosts for supramolecular chemistry of fullerenes. Chem Soc Rev 36:189–197
Kawase T, Kurata H (2006) Ball-, bowl-, and belt-shaped conjugated systems and their complexing abilities: exploration of the concave-convex π−π interaction. Chem Rev 106:5250–5273
Mizyed S, Georghiou PE, Bancu M et al (2001) Embracing C60 with multiarmed geodesic partners. J Am Chem Soc 123:12770–12774
Sygula A, Fronczek FR, Sygula R et al (2007) A double concave hydrocarbon buckycatcher. J Am Chem Soc 129:3842–3843
Pérez EM, Martín N (2010) Molecular tweezers for fullerenes. Pure Appl Chem 82:523–533
Kawase T, Darabi HR, Oda M (1996) Cyclic [6]- and [8]paraphenylacetylenes. Angew Chem Int Ed 35:2664–2666
Kawase T, Tanaka K, Fujiwara N et al (2003) Complexation of a carbon nanoring with fullerenes. Angew Chem Int Ed 42:1624–1628
Kawase T, Tanaka K, Seirai Y et al (2003) Complexation of carbon nanorings with fullerenes: supramolecular dynamics and structural tuning for a fullerene sensor. Angew Chem Int Ed 42:5597–5600
Omachi H, Segawa Y, Itami K (2012) Synthesis of cycloparaphenylenes and related carbon nanorings: a step toward the controlled synthesis of carbon nanotubes. Acc Chem Res 45:1378–1389
Iwamoto T, Watanabe Y, Sadahiro T et al (2011) Size-selective encapsulation of C60 by [10]cycloparaphenylene: formation of the shortest fullerene-peapod. Angew Chem Int Ed 50:8342–8344
Xia J, Bacon JW, Jasti R (2012) Gram-scale synthesis and crystal structures of [8]- and [10]CPP, and the solid-state structure of C60·[10]CPP. Chem Sci 3:3018–3021
Pérez EM, Sánchez L, Fernández G et al (2006) exTTF as a building block for fullerene receptors. Unexpected solvent-dependent positive homotropic cooperativity. J Am Chem Soc 128:7172–7173
Gayathri SS, Wielopolski M, Pérez EM et al (2009) Discrete supramolecular donor-acceptor complexes. Angew Chem Int Ed 48:815–819
Pérez EM, Capodilupo AL, Fernández G et al (2008) Weighting non-covalent forces in the molecular recognition of C60. Relevance of concave-convex complementarity. Chem Commun 4567–4569
Pérez EM, Martín N (2012) Chiral recognition of carbon nanoforms. Org Biomol Chem 10:3577–3583
Pérez EM, Sierra M, Sánchez L et al (2007) Concave tetrathiafulvalene-type donors as supramolecular partners for fullerenes. Angew Chem Int Ed 46:1847–1851
Haino T, Yanase M, Fukazawa Y (1998) Fullerenes enclosed in bridged calix[5]arenes. Angew Chem Int Ed 37:997–998
Uno H, Furukawa M, Fujimoto A et al (2011) Porphyrin molecular tweezers for fullerenes. J Porphyr Phthalocyanins 15:951–963
Sun D, Tham FS, Reed CA et al (2000) Porphyrin-fullerene host-guest chemistry. J Am Chem Soc 122:10704–10705
Sun D, Tham FS, Reed CA et al (2002) Supramolecular fullerene-porphyrin chemistry. Fullerene complexation by metalated “jaws porphyrin” hosts. J Am Chem Soc 124:6604–6612
Hosseini A, Taylor S, Accorsi G et al (2006) Calix[4]arene-linked bisporphyrin hosts for fullerenes: binding strength, solvation effects, and porphyrin-fullerene charge transfer bands. J Am Chem Soc 128:15903–15913
Ayabe M, Ikeda A, Shinkai S et al (2002) A novel [60]fullerene receptor with a Pd(II)-switched bisporphyrin cleft. Chem Commun 1032–1033
Fernández G, Pérez EM, Sánchez L et al (2008) Self-organization of electroactive materials: a head-to-tail donor-acceptor supramolecular polymer. Angew Chem Int Ed 47:1094–1097
Fernández G, Pérez EM, Sánchez L et al (2008) An electroactive dynamically polydisperse supramolecular dendrimer. J Am Chem Soc 130:2410–2411
Santos J, Pérez EM, Illescas BM et al (2011) Linear and hyperbranched electron-acceptor supramolecular oligomers. Chem Asian J 6:1848–1853
Fernández G, Sánchez L, Pérez EM et al (2008) Large exTTF-based dendrimers. Self-assembly and peripheral cooperative multiencapsulation of C60. J Am Chem Soc 130:10674–10683
Canevet D, Pérez EM, Martín N (2011) Wraparound hosts for fullerenes: tailored macrocycles and cages. Angew Chem Int Ed 50:9248–9259
Tashiro K, Aida T, Zheng J-Y et al (1999) A cyclic dimer of metalloporphyrin forms a highly stable inclusion complex with C60. J Am Chem Soc 121:9477–9478
Yanagisawa M, Tashiro K, Yamasaki M et al (2007) Hosting fullerenes by dynamic bond formation with an iridium porphyrin cyclic dimer: a “chemical friction” for rotary guest motions. J Am Chem Soc 129:11912–11913
Gil-Ramírez G, Karlen SD, Shundo A et al (2010) A cyclic porphyrin trimer as a receptor for fullerenes. Org Lett 12:3544–3547
Song J, Aratani N, Shinokubo H et al (2010) A porphyrin nanobarrel that encapsulates C60. J Am Chem Soc 132:16356–16357
Zheng J-Y, Tashiro K et al (2001) Cyclic dimers of metalloporphyrins as tunable hosts for fullerenes: a remarkable effect of rhodium(III). Angew Chem Int Ed 40:1857–1861
Isla H, Gallego M, Pérez EM et al (2010) A bis-exTTF macrocyclic receptor that associates C60 with micromolar affinity. J Am Chem Soc 132:1772–1773
Canevet D, Gallego M, Isla H et al (2011) Macrocyclic hosts for fullerenes: extreme changes in binding abilities with small structural variations. J Am Chem Soc 133:3184–3190
Akasaka T, Wudl F, Nagase S (2010) Chemistry of nanocarbons. Wiley-VCH, Chichester
Yamada M, Akasaka T, Nagase S (2010) Endohedral metal atoms in pristine and functionalized fullerene cages. Acc Chem Res 43:92–102
Lu X, Akasaka T, Nagase S (2012) Chemistry of endohedral metallofullerenes: the role of metals. Chem Commun 47:5942–5957
Rodríguez-Fortea A, Balch AL, Poblet JM (2011) Endohedral metallofullerenes: a unique host-guest association. Chem Soc Rev 40:3551–3563
Dunsch L, Yang S (2007) Metal nitride cluster fullerenes: their current state and future prospects. Small 3:1298–1320
Stevenson S, Mackey MA, Stuart MA et al (2008) A distorted tetrahedral metal oxide cluster inside an icosahedral carbon cage. Synthesis, isolation, and structural characterization of Sc4(mu3-O)2@Ih-C80. J Am Chem Soc 130:11844–11845
Chaur MN, Melin F, Ortiz AL et al (2009) Chemical, electrochemical, and structural properties of endohedral metallofullerenes. Angew Chem Int Ed 48:7514–7538
Saunders M, Jiménez-Vázquez HA, Cross RJ et al (1993) Stable compounds of helium and neon. He@C60 and Ne@C60. Science 259:1428–1430
Kurotobi K, Murata Y (2011) A single molecule of water encapsulated in fullerene C60. Science 333:613–616
Campanera JM, Bo C, Olmstead MM et al (2002) Bonding within the endohedral fullerenes Sc3N@C78 and Sc3N@C80 as determined by density functional calculations and reexamination of the crystal structure of {Sc3N@C78}·Co(OEP)}·1.5(C6H6)·0.3(CHCl3). J Phys Chem A 106:12356–12364
Aoyagi S, Nishibori E, Sawa H et al (2010) A layered ionic crystal of polar Li@C60 superatoms. Nat Chem 2:678–683
Aoyagi S, Sado Y, Nishibori E et al (2012) Rock-salt-type crystal of thermally contracted C60 with encapsulated lithium cation. Angew Chem Int Ed 51:3377–3381
Chai Y, Guo T, Jin C et al (1991) Fullerenes with metals inside. J Phys Chem 95:7564–7568
Nagase S, Kobayashi K (1994) The ionization energies and electron affinities of endohedral metallofullerenes MC82(M = Sc, Y, La): density functional calculations. J Chem Soc Chem Commun 1837–1838
Tsuchiya T, Sato K, Kurihara H et al (2006) Spin-site exchange system constructed from endohedral metallofullerenes and organic donors. J Am Chem Soc 128:14418–14419
Sato S, Seki S, Honsho Y et al (2011) Semi-metallic single-component crystal of soluble La@C82 derivative with high electron mobility. J Am Chem Soc 133:2766–2771
Feng L, Tsuchiya T, Wakahara T et al (2006) Synthesis and characterization of a bisadduct of La@C82. J Am Chem Soc 128:5990–5991
Wakahara T, Yamada M, Takahashi S et al (2007) Two-dimensional hopping motion of encapsulated La atoms in silylated La2@C80. Chem Commun 2680–2682
Yamada M, Mizorogi N, Tsuchiya T et al (2009) Synthesis and characterization of the D 5h isomer of the endohedral dimetallofullerene Ce2@C80: two-dimensional circulation of encapsulated metal atoms inside a fullerene cage. Chemistry 15:9486–9493
Stevenson S, Rice G, Glass T et al (1999) Small-bandgap endohedral metallofullerenes in high yield and purity. Nature 401:55–57
Popov AA, Dunsch L (2007) Structure, stability, and cluster-cage interactions in nitride clusterfullerenes M3N@C2n (M = Sc, Y; 2n = 68–98): a density functional theory study. J Am Chem Soc 129:11835–11849
Rodríguez-Fortea A, Alegret N, Balch AL et al (2010) The maximum pentagon separation rule provides a guideline for the structures of endohedral metallofullerenes. Nat Chem 2:955–961
Stevenson S, Phillips JP, Reid JE et al (2004) Pyramidalization of Gd3N inside a C80 cage. The synthesis and structure of Gd3N@C80. Chem Commun 2814–2815
Chaur MN, Melin F, Elliott B et al (2007) Gd3N@C2n (n = 40, 42, and 44): remarkably low HOMO-LUMO gap and unusual electrochemical reversibility of Gd3N@C88. J Am Chem Soc 129:14826–14829
Chaur MN, Melin F, Ashby J et al (2008) Lanthanum nitride endohedral fullerenes La3N@C2n (43< or =n< or =55): preferential formation of La3N@C96. Chemistry 14:8213–8219
Cao B, Wakahara T, Maeda Y et al (2004) Lanthanum endohedral metallofulleropyrrolidines: synthesis, isolation, and EPR characterization. Chemistry 10:716–720
Cardona CM, Kitaygorodskiy A, Echegoyen L (2005) Trimetallic nitride endohedral metallofullerenes: reactivity dictated by the encapsulated metal cluster. J Am Chem Soc 127:10448–10453
Yamada M, Someya C, Wakahara T et al (2008) Metal atoms collinear with the spiro carbon of 6,6-open adducts, M2@C80(Ad) (M = La and Ce, Ad = adamantylidene). J Am Chem Soc 130:1171–1176
Shustova NB, Popov AA, Mackey MA et al (2007) Radical trifluoromethylation of Sc3N@C80. J Am Chem Soc 129:11676–11677
Shu C, Cai T, Xu L et al (2007) Manganese(III)-catalyzed free radical reactions on trimetallic nitride endohedral metallofullerenes. J Am Chem Soc 129:15710–15717
Iezzi EB, Duchamp JC, Harich K (2002) A symmetric derivative of the trimetallic nitride endohedral metallofullerene, Sc3N@C80. J Am Chem Soc 124:524–525
Lee HM, Olmstead MM, Iezzi E et al (2002) Crystallographic characterization and structural analysis of the first organic functionalization product of the endohedral fullerene Sc3N@C80. J Am Chem Soc 124:3494–3495
Ge Z, Duchamp JC, Cai T et al (2005) Purification of endohedral trimetallic nitride fullerenes in a single, facile step. J Am Chem Soc 127:16292–16298
Cai T, Ge Z, Iezzi EB et al (2005) Synthesis and characterization of the first trimetallic nitride templated pyrrolidino endohedral metallofullerenes. Chem Commun 3594–3596
Wakahara T, Iiduka Y, Ikenaga O et al (2006) Characterization of the bis-silylated endofullerene Sc3N@C80. J Am Chem Soc 128:9919–9925
Yamada M, Minowa M, Sato S et al (2011) Regioselective cycloaddition of La2@I h -C80 with tetracyanoethylene oxide: formation of an endohedral dimetallofullerene adduct featuring enhanced electron-accepting character. J Am Chem Soc 33:3796–3799
Liu T-X, Wei T, Zhu S-E et al (2012) Azide addition to an endohedral metallofullerene: formation of azafulleroids of Sc3N@I h -C80. J Am Chem Soc 134:11956–11959
Yamada M, Nakahodo T, Wakahara T et al (2005) Positional control of encapsulated atoms inside a fullerene cage by exohedral addition. J Am Chem Soc 127:14570–14571
Yamada M, Wakahara T, Nakahodo T et al (2006) Synthesis and structural characterization of endohedral pyrrolidinodimetallofullerene: La2@C80(CH2)2NTrt. J Am Chem Soc 128:1402–1403
Cardona CM, Elliott B, Echegoyen L (2006) Unexpected chemical and electrochemical properties of M3N@C80 (M = Sc, Y, Er). J Am Chem Soc 128:6480–6485
Rodríguez-Fortea A, Campanera JM, Cardona CM et al (2006) Dancing on a fullerene surface: isomerization of Y3N@(N-ethylpyrrolidino-C80) from the 6,6 to the 5,6 regioisomers. Angew Chem Int Ed 45:8176–8180
Pinzón JR, Plonska-Brzezinska ME, Cardona CM et al (2008) Sc3N@C80-ferrocene electron-donor/acceptor conjugates as promising materials for photovoltaic applications. Angew Chem Int Ed 47:4173–4176
Takano Y, Herranz MA, Martín N et al (2010) Donor-acceptor conjugates of lanthanum endohedral metallofullerene and π-extended tetrathiafulvalene. J Am Chem Soc 132:8048–8055
Li FF, Pinzón JR, Mercado BQ et al (2011) [2+2]Cycloaddition reaction to Sc3N@I h -C80. The formation of very stable [5,6]- and [6,6]-adducts. J Am Chem Soc 133:1563–1571
Wang GW, Liu TX, Jiao M et al (2011) The cycloaddition reaction of I h -Sc3N@C80 with 2-amino-4,5-diisopropoxybenzoic acid and isoamyl nitrite to produce an open-cage metallofullerene. Angew Chem Int Ed 50:4658–4662
Lukoyanova O, Cardona CM, Rivera J et al (2007) Open rather than closed malonate methano-fullerene derivatives. The formation of methanofulleroid adducts of Y3N@C80. J Am Chem Soc 129:10423–10430
Cai T, Xu L, Shu C et al (2008) Selective formation of a symmetric Sc3N@C78 bisadduct: adduct docking controlled by an internal trimetallic nitride cluster. J Am Chem Soc 130:2136–2137
Rudolf M, Wolfrum S, Guldi DM et al (2012) Endohedral metallofullerenes–filled fullerene derivatives towards multifunctional reaction center mimics. Chemistry 8:5136–48
Feng L, Rudolf M, Wolfrum S et al (2012) A paradigmatic change: linking fullerenes to electron acceptors. J Am Chem Soc 34:12190–12197
Li FF, Rodríguez-Fortea A, Poblet JM et al (2011) Reactivity of metallic nitride endohedral metallofullerene anions: electrochemical synthesis of a Lu3N@I h -C80 derivative. J Am Chem Soc 133:2760–2765
Li FF, Rodríguez-Fortea A, Peng P et al (2012) Electrosynthesis of a Sc3N@I h -C80 methano derivative from trianionic Sc3N@Ih-C80. J Am Chem Soc 134:480–7487
Tsuchiya T, Wielopolski M, Sakuma N et al (2011) Stable radical anions inside fullerene cages: formation of reversible electron transfer systems. J Am Chem Soc 133:13280–13283
Armaroli N, Balzani V (2007) The future of energy supply: challenges and opportunities. Angew Chem Int Ed 46:52–66
Chapin DM, Fuller CS, Pearson GL (1954) A new silicon p‐n junction photocell for converting solar radiation into electrical power. J Appl Chem 25:676–678
Rispens MT, Hummelen JC (2002) Fullerenes: from synthesis to optoelectronic properties. In: Guldi DM, Martín N (eds) Photovoltaic applications. Kluwer Academic, Dordrech, pp 387–435 (Chap. 12)
Hummelen JC, Knight BW, LePeq F et al (1995) Preparation and characterization of fulleroid and methanofullerene derivatives. J Org Chem 60:532–538
Yu G, Gao J, Hummelen JC et al (1995) Polymer photovoltaic cells: enhanced efficiencies via a network of internal donor-acceptor heterojunctions. Science 270:1789–1791
Zhang Y, Yip HL, Acton O et al (2009) A simple and effective way of achieving highly efficient and thermally stable bulk-heterojunction polymer solar cells using amorphous fullerene derivatives as electron acceptor. Chem Mater 21:2598–2600
Lenes L, Wetzelaer GJAH, Kooistra FB et al (2008) Fullerene bisadducts for enhanced open-circuit voltages and efficiencies in polymer solar cells. Adv Mater 20:2116–2119
Wienk MM, Kroon JM, Verhees WJH et al (2003) Efficient methano[70]fullerene/MDMO-PPV bulk heterojunction photovoltaic cells. Angew Chem Int Ed 42:3371–3375
Park SH, Roy A, Beaupré S et al (2009) Bulk heterojunction solar cells with internal quantum efficiency approaching 100%. Nat Photonics 3:297–302
Kooistra FB, Mihailetchi VD, Popescu LM et al (2006) New C84 derivative and its application in a bulk heterojunction solar cell. Chem Mater 18:3068–3073
Li CZ, Yip HL, Jen AKY (2012) Functional fullerenes for organic photovoltaics. J Mater Chem 22:4161–4177
Riedel I, von Hauff E, Parisi J et al (2005) Diphenylmethanofullerenes: new and efficient acceptors in bulk-heterojunction solar cells. Adv Funct Mater 15:1979–1987
Riedel I, Martín N, Giacalone F et al (2004) Polymer solar cells with novel fullerene-based acceptor. Thin Solid Films 451:43–47
Backer S, Sivula K, Kavulak DF et al (2007) High efficiency organic photovoltaics incorporating a new family of soluble fullerene derivatives. Chem Mater 19:2927–2929
He Y, Chen HY, Hou J et al (2010) Indene–C60 bisadduct: a new acceptor for high-performance polymer solar cells. J Am Chem Soc 132:1377–1382
Weiss EA, Wasielewski MR, Ratner MA (2005) Molecules as wires: molecule-assisted movement of charge and energy. Top Curr Chem 257:103–133
Guldi DM, Illescas BM, Atienza CM et al (2009) Fullerene for organic electronics. Chem Soc Rev 38:1587–1597
Ito O, Yamanaka K (2009) Roles of molecular wires between fullerenes and electron donors in photoinduced electron transfer. Bull Chem Soc Jpn 82:316–332
Vail SA, Schuster DI, Guldi DM et al (2006) Energy and electron transfer in beta-alkynyl-linked porphyrin-[60]fullerene dyads. J Phys Chem B 110:14155–14166
Vail SA, Krawczuk PJ, Guldi DM et al (2005) Energy and electron transfer in polyacetylene-linked zinc–porphyrin–[60]fullerene molecular wires. Chemistry 11:3375–3388
Tashiro K, Sato A, Yuzawa T et al (2006) Long-range photoinduced electron transfer mediated by oligo-p-phenylenebutadiynylene conjugated bridges. Chem Lett 35:518–519
Lembo A, Tagliatesta P, Guldi DM et al (2009) Porphyrin-β-oligo-ethynylenephenylene-[60]fullerene triads: synthesis and electrochemical and photophysical characterization of the new porphyrin-oligo-PPE-[60]fullerene systems. J Phys Chem A 113:1779–1793
Giacalone F, Segura JL, Martín N et al (2004) Exceptionally small attenuation factors in molecular wires. J Am Chem Soc 126:5340–5341
Giacalone F, Segura JL, Martín N et al (2005) Probing molecular wires: synthesis, structural, and electronic study of donor-acceptor assemblies exhibiting long-range electron transfer. Chemistry 11:4819–4834
de la Torre G, Giacalone F, Segura JL et al (2005) Electronic communication through π-conjugated wires in covalently linked porphyrin/C60 ensembles. Chemistry 11:12671280
Molina-Ontoria A, Wielopolski M, Gebhardt J (2011) [2,2′]Paracyclophane-based π-conjugaed molecular wires reveal molecular-junction behavior. J Am Chem Soc 133:2370–2373
Atienza-Castellanos C, Wielopolski M, Guldi DM et al (2007) Determination of the attenuation factor in fluorene-based molecular wires. Chem Commun 5164–5166
Wielopolski M, Santos J, Illescas BM et al (2011) Vinyl spacers – tuning electron transfer through fluorene-based molecular wires. Energy Environ Sci 4:765–771
Ikemoto J, Takimiya K, Aso Y et al (2002) Porphyrin–oligothiophene–fullerene triads as an efficient intramolecular electron-transfer system. Org Lett 4:309–311
Nakamura T, Fujitsuka M, Araki Y et al (2004) Photoinduced electron transfer in porphyrin-oligothiophene-fullerene linked triads by excitation of a porphyrin moiety. J Phys Chem B 108:10700–10710
Wessendorf F, Grimm B, Guldi DM et al (2010) Pairing fullerenes and porphyrins: supramolecular wires that exhibit charge transfer activity. J Am Chem Soc 132:10786–10795
Schmalz TG, Seitz WA, Klein DJ et al (1986) C60 carbon cages. Chem Phys Lett 130:203–207
Schein S, Friedrich TA (2008) A geometric constraint, the head-to-tail exclusion rule, may be the basis for the isolated-pentagon rule in fullerenes with more than 60 vertices. Proc Natl Acad Sci U S A 105:19142–19147
Tan T-Z, Li J, Zhu F et al (2010) Chlorofullerenes featuring triple sequentially fused pentagons. Nat Chem 2:269–273
Martín N (2011) Fullerene C72Cl4: the exception that proves the rule? Angew Chem Int Ed 50:5431–5433
Tan Y-Z, Xie S-Y, Huang R-B et al (2009) The stabilization of fused-pentagon fullerene molecules. Nat Chem 1:450–460
Wang CR, Kai T, Tomiyama T et al (2000) Materials science – C66 fullerene encaging a scandium dimer. Nature 408:426–427
Stevenson S, Fowler PW, Heine T et al (2000) Materials science: a stable non-classical metallofullerene family. Nature 408:427–428
Beavers CM, Zuo TM, Duchamp JC et al (2006) Tb3N@C84: an improbable, egg-shaped endohedral fullerene that violates the isolated pentagon rule. J Am Chem Soc 128:11352–11353
Yang SF, Popov AA, Dunsch L (2007) Violating the isolated pentagon rule (IPR): the endohedral non-IPR C70 cage of Sc3N@C70. Angew Chem Int Ed 46:1256–1259
Ma YH, Wang TS, Wu JY et al (2011) Size effect of endohedral cluster on fullerene cage: preparation and structural studies of Y3N@C78-C2. Nanoscale 3:4955–4957
Shi ZQ, Wu X, Wang CR et al (2006) Isolation and characterization of Sc2C2@C68: a metal-carbide endofullerene with a non-IPR carbon cage. Angew Chem Int Ed 45:2107–2111
Wu JY, Wang TS, Ma YH et al (2011) Synthesis, isolation, characterization, and theoretical studies of Sc3NC@C78-C2. J Phys Chem C 115:23755–23759
Campanera JM, Bo C, Poblet JM (2005) General rule for the stabilization of fullerene cages encapsulating trimetallic nitride templates. Angew Chem Int Ed 44:7230–7233
Summerscales OT, Cloke FGN (2006) The organometallic chemistry of pentalene. Coord Chem Rev 250:1122–1140
Xie SY, Gao F, Lu X et al (2004) Capturing the labile fullerene[50] as C50Cl10. Science 304:699–699
Wang CR, Shi ZQ, Wan LJ et al (2006) C64H4: production, isolation, and structural characterizations of a stable unconventional fulleride. J Am Chem Soc 128:6605–6610
Li B, Shu CY, Lu X et al (2010) Addition of carbene to the equator of C(70) to produce the most stable C(71)H(2) isomer: 2 aH-2(12)a-homo(C(70)-D(5 h(6)))[5,6]fullerene. Angew Chem Int Ed 49:962–966
Tan YZ, Li J, Zhou T, Feng YQ et al (2010) Pentagon-fused hollow fullerene in C78 family retrieved by chlorination. J Am Chem Soc 132:12648–12652
Kato H, Taninaka A, Sugai T et al (2003) Structure of a missing-caged metallofullerene: La2@C72. J Am Chem Soc 125:7782–7783
Yamada M, Wakahara T, Tsuchiya T et al (2008) Spectroscopic and theoretical study of endohedral dimetallofullerene having a non-IPR fullerene cage: Ce2@C72. J Phys Chem A 112:7627–7631
Wakahara T, Nikawa H, Kikuchi T et al (2006) La@C72 having a non-IPR carbon cage. J Am Chem Soc 128:14228–14229
Chen N, Beavers CM, Mulet-Gas M et al (2012) Sc2S@C(s)(10528)-C72: a dimetallic sulfide endohedral fullerene with a non isolated pentagon rule cage. J Am Chem Soc 134:7851–7860
Tan Y-Z, Zhou T, Bao J, Shan G-J, Xie S-Y, Huang R-B, Zheng L-S (2010) C72Cl4: a pristine fullerene with favorable pentagon-adjacent structure. J Am Chem Soc 132:17102–17104
Ziegler K, Mueller A, Amsharov KY, Jansen M (2010) Disclosure of the elusive C2v-C72 carbon cage. J Am Chem Soc 132:17099–17101
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2013 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Delgado, J.L. et al. (2013). Buckyballs. In: Siegel, J., Wu, YT. (eds) Polyarenes II. Topics in Current Chemistry, vol 350. Springer, Cham. https://doi.org/10.1007/128_2012_414
Download citation
DOI: https://doi.org/10.1007/128_2012_414
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-319-07301-9
Online ISBN: 978-3-319-07302-6
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)