Fullerenes: Formation, stability, and reactivity

Wiley Interdisciplinary Reviews: Computational Molecular Science

Volumn 1, Issue 3, 2011, Pages 350-367

  Rodríguez Fortea, Antonio ^a   Irle, Stephan ^b   Poblet, Josep M ^a  

^a UNIVERSITAT ROVIRA I VIRGILI   (Spain)

^b NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AB INITIO; ELECTRON TRANSFER; ENDOHEDRAL FULLERENE; ENDOHEDRAL METALLOFULLERENES; FORMATION MECHANISM; SEMI-EMPIRICAL METHODS; THEORETICAL STUDY;

DENSITY FUNCTIONAL THEORY; STABILIZATION;

FULLERENES;

EID: 84860719476     PISSN: 17590876     EISSN: 17590884     Source Type: Journal    
DOI: 10.1002/wcms.21     Document Type: Review

References (116)

1. 60-buckminsterfullerene. Nature 1985, 318:162-163.
2. 70. Nature 1987, 329:529-531.
3. Achiba Y, Kikuchi K, Aihara Y, Wakabayashi T, Miyake Y, Kainosho M. The Chemical Physics of Fullerenes 10 (and 5) Years Later. Dordrecht, the Netherlands: Kluwer Academic Publishers; 1996.
4. Newton MD, Stanton RE. Stability of buckminsterfullerene and related carbon clusters. J Am Chem Soc 1986, 108:2469-2470.
5. 60 molecule buckminsterfullerene. Chem Phys Lett 1987, 135:357-360.
6. Andreoni W. Computational approach to the physical chemistry of fullerenes and their derivatives. Ann Rev Phys Chem 1998, 49:405-439.
7. 60-a new form of carbon. Nature 1990, 347:354-358.
8. 60, buckminsterfullerene. J Am Chem Soc 1986, 108:1301-1302.
9. Liu X, Schmalz TG, Klein DJ. Favorable structures for higher fullerenes. Chem Phys Lett 1992, 188:550-554.
10. Schein S, Friedrich T. 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 USA 2008, 105:19142-19147.
11. Fowler PW, Manolopoulos DE. An Atlas of Fullerenes. Oxford: Oxford University Press; 1995.
12. 60 and application to nmr. Chem Phys Lett 1991, 182:257-262.
13. Yoshida M, Osawa E. Formalized drawing of fullerene nets. 1. Algorithm and exhaustive generation of isomeric structures. Bull Chem Soc Jpn 1995, 68:2073-2081.
14. 80. Angew Chem Int Ed Engl 1996, 35:1732-1734.
15. 80 fullerene. Chem Commun 2000:557-558.
16. 80. Int J Quantum Chem 2006, 106:2222-2228.
17. 120. J Phys Chem C 2007, 111:17671-17677.
18. 80: are there still more isomers? J Chem Phys 2001, 114:10362-10367.
19. 110. J Phys Chem A 2006, 110:7672-7676.
20. Cioslowski J, Rao N, Moncrieff D. Standard enthalpies of formation of fullerenes and their dependence on structural motifs. J Am Chem Soc 2000, 122:8265-8270.
21. 160. J Phys Chem A 2006, 110:9247-9253.
22. 96 IPR fullerenes. J Phys Chem A 2004, 108:4479-4484.
23. 94. J Chem Phys 2003, 118:10534-10540.
24. Minami T, Miyake Y, Kikuchi K, Achiba Y. The 18th Fullerene General Symposium. Okazaki, Japan: Fullerene Research Association of Japan; 2000.
25. Dunlap BI, Zope RR. Efficient quantum-chemical geometry optimization and the structure of large icosahedral fullerenes. Chem Phys Lett 2006, 422:451-454.
26. 540. Chem Phys Lett 1995, 243:193-198.
27. 2160 characterized by an all-electron density functional theory. Phys Rev B 2008, 77:115452.
28. Dunlap BI, Boettger JC. Local-density-functional study of the fullerenes, graphene, and graphite. J Phys B At Mol Opt Phys 1996, 29:4907-4913.
29. Janetzko F, Koster AM, Salahub DR. Development of the cyclic cluster model formalism for Kohn-Sham auxiliary density functional theory methods. J Chem Phys 2008, 128:024102.
30. Calaminici P, Geudtner G, Koster AM. First-principle calculations of large fullerenes. J Chem Theory Comput 2009, 5:29-32.
31. 60 evaluated with the MPWB1K functional. J Chem Theory Comput 2006, 2:782-785.
32. Stevenson S, Rice G, Glass T, Harich K, Cromer F, et al. Small-bandgap endohedral metallofullerenes in high yield and purity. Nature 1999, 401:55-57.
33. 6+@C2n6- model. Angew Chem Int Ed 2009, 48:1425-1428.
34. Stevenson S, Fowler PW, Heine T, Duchamp JC, Rice G, et al. Materials science - a stable non-classical metallofullerene family. Nature 2000, 408:427-428.
35. Tan YZ, Xie SY, Huang RB, Zheng LS. The stabilization of fused-pentagon fullerene molecules. Nature Chem 2009, 1:450-460.
36. Campanera JM, Bo C, Poblet JM. General rule for the stabilization of fullerene cages encapsulating trimetallic nitride templates. Angew Chem Int Ed 2005, 44:7230-7233.
37. 2n (M = Sc, Y; 2n = 68-98): a density functional study). J Am Chem Soc 2007, 129:11835-11849.
38. Chaur MN, Melin F, Ortiz AL, Echegoyen L. Chemical, electrochemical, and structural properties of endohedral metallofullerenes. Angew Chem Int Ed 2009, 48:7514-7538.
39. 82 and related systems. J Phys Chem A 2008, 112:4550-4555.
40. Albertazzi E, Domene C, Fowler PW, Heine T, Seifert G, et al. Pentagon adjacency as a determinant of fullerene stability. Phys Chem Chem Phys 1999, 1:2913-2918.
41. Fowler PW, Zerbetto F. Charging and equilibration of fullerene isomers. Chem Phys Lett 1995, 243:36-41.
42. Wang Y, Zettergren H, Alcami M, Martin F. Stability of multiply charged fullerene anions and cations. Phys Rev A 2009, 80:033201.
43. 70 fullerenes containing a uniform distribution of pyrenes and adjacent pentagons. Chemphyschem 2008, 9:861-866.
44. Rodríguez-Fortea A, Alegret N, Balch A, Poblet JM. Nature Chem 2010, 2:955-961.
45. 84: An improbable, egg-shaped endohedral fullerene that violates the isolated pentagon rule. J Am Chem Soc 2006, 128:11352-11353.
46. Chai Y, Guo T, Jin CM, Haufler RE, Chibante LPF, et al. Fullerenes with metals inside. J Phys Chem 1991, 95:7564-7568.
47. 82 (M = Sc, Y and La). Chem Phys Lett 1998, 282:325-329.
48. 3). J Phys Chem A 2002, 106:12356-12364.
49. Popov AA, Dunsch L. Bonding in endohedral metallofullerenes as studied by quantum theory of atoms in molecules. Chem Eur J 2009, 15:9707-9729.
50. Yamada M, Akasaka T, Nagase S. Endohedral metal atoms in pristine and functionalized fullerene cages. Acc Chem Res 2009, 43:92-102.
51. 2NTrt. J Am Chem Soc 2006, 128:1402-1403.
52. 80. Are the metal atoms still inside the fullerene cages? Chem Phys Lett 1996, 261:502-506.
53. 3N@C80-, and spatial spin-charge separation as a general principle for anions of endohedral fullerenes with metal-localized lowest unoccupied molecular orbitals. J Am Chem Soc 2008, 130:17726-17742.
54. 2n (M = Sc, Y, La, and Gd; 2n = 80, 84, 88, 92, 96). Chem Eur J 2009, 15:10997-11009.
55. Valencia R, Rodriguez-Fortea A, Poblet JM. Large fullerenes stabilized by encapsulation of metallic clusters. Chem Commun 2007:4161-4163.
56. Popov AA. Metal-cage bonding, molecular structures and vibrational spectra of endohedral fullerenes: Bridging experiment and theory. J Comput Theor Nanosci 2009, 6:292-317.
57. 68: Synthesis, spectroscopic characterization, and density functional theory computations (IPR = isolated pentagon rule). Chem Eur J 2006, 12:7856-7863.
58. 70. Angew Chem Int Ed 2007, 46:1256-1259.
59. 76. J Phys Chem B 2007, 111:13659-13663.
60. 78 cage isomerism defined by trimetallic nitride cluster size: A computational and vibrational spectroscopic study. J Phys Chem B 2007, 111:3363-3369.
61. 80 (n = 2, 3). Inorg Chem 2009, 48:5957-5961.
62. 80: A density functional theory investigation. J Phys Chem A 2006, 110:1171-1176.
63. 80. J Phys Chem B 2006, 110:11098-11102.
64. 80 and its monoanion. Phys Chem Chem Phys 2008, 10:7158-7168.
65. 80 with nitrogen substituted by a pseudoatom. ACS Nano 2010, 4:795-802.
66. Hirsch A, Brettreich M. Fullerenes: Chemistry and Reactions. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KgaA; 2005.
67. Haddon RC. Chemistry of the fullerenes-the manifestation of strain in a class of continuous aromatic molecules. Science 1993, 261:1545-1550.
68. Haddon RC. Pi-electrons in 3 dimensions. Acc Chem Res 1988, 21:243-249.
69. 60) in a Diels-Alder model reaction. Chem Phys Lett 1994, 231:325-330.
70. 2 extrusion to form monoimino- 60 fullerenes. J Org Chem 2001, 66:433-442.
71. 60. J Phys Chem 1996, 100:7449-7454.
72. 60: a theoretical investigation on their mechanism and regioselectivity. J Org Chem 2005, 70:5426-5435.
73. Alvarez A, Ochoa E, Verdecia Y, Suarez M, Sola M, Martin N. Theoretical study of the highly diastereoselective 1, 3-dipolar cycloaddition of 1, 4-dihydropyridine-containing azomethine ylides to 60 fullerene (Prato's reaction). J Org Chem 2005, 70:3256-3262.
74. Filippone S, Barroso MI, Martin-Domenech A, Osuna S, Sola M, Martin N. On the mechanism of the thermal retrocycloaddition of pyrrolidinofullerenes (retro-Prato reaction). Chem Eur J 2008, 14:5198-5206.
75. Martin N, Altable M, Filippone S, Martin-Domenech A, Guell M, Sola M. Thermal 2+2 intramolecular cycloadditions of fuller-1, 6-enynes. Angew Chem Int Ed 2006, 45:1439-1442.
76. Osuna S, Houk KN. Cycloaddition reactions of butadiene and 1, 3-dipoles to curved arenes, fullerenes, and nanotubes: Theoretical evaluation of the role of distortion energies on activation barriers. Chem Eur J 2009, 15:13219-13231.
77. 60: an analysis of the performance of the ONIOM method for the study of chemical reactivity in fullerenes and nanotubes. J Phys Chem A 2009, 113:9721-9726.
78. 60 from the trichloromethyl anion: carbene mechanism or Bingel mechanism? J Phys Chem A 2009, 113:3673-3676.
79. 60: a theoretical study. Chem Eur J 2007, 13:6171-6178.
80. 60. J Phys Chem A 2001, 105:7634-7637.
81. 24. Angew Chem Int Ed 2009, 48:5904-5907.
82. 90. J Am Chem Soc 2008, 130:13471-13489.
83. Fatouros PP, Corwin FD, Chen ZJ, Broaddus WC, Tatum JL, et al. In vitro and in vivo imaging studies of a new endohedral metallofullerene nanoparticle. Radiology 2006, 240:756-764.
84. 82. Nature 1995, 374:600-601.
85. 2NTrt (M = La, Ce; Trt = trityl): Control of metal atom positions by addition positions. Chem Eur J 2009, 15:10533-10542.
86. Sola M, Mestres J, Duran M. Molecular size and pyramidalyzation - two keys for understanding the reactivity of fullerenes. J Phys Chem 1995, 99:10752-10758.
87. Campanera JM, Bo C, Poblet JM. Exohedral reactivity of trimetallic nitride template (TNT) endohedral metallofullerenes. J Org Chem 2006, 71:46-54.
88. 80. J Am Chem Soc 2007, 129:10423-10430.
89. 80 (M = Sc, Y, Er). J Am Chem Soc 2006, 128:6480-6485.
90. 80) from the 6, 6 to the 5, 6 regioisomer. Angew Chem Int Ed 2006, 45:8176-8180.
91. 3N encapsulation. J Am Chem Soc 2008, 130:6206-6214.
92. 78: Encapsulated cluster regiocontrol of adduct docking on an ellipsoidal metallofullerene sphere. J Am Chem Soc 2007, 129:10795-10800.
93. 80. J Phys Chem B 2005, 109:4024-4031.
94. 80. J Am Chem Soc 2007, 129:11676-+.
95. 70 in flames. Nature 1991, 352:139-141.
96. 3 radical densities in laser-ablation carbon plumes measured by laser-induced fluorescence imaging spectroscopy. J Appl Phys 2002, 91:4033-4039.
97. 70 growth mechanism. Chem Phys Lett 1992, 190:465-468.
98. 60. Rev Mod Phys 1997, 69:703-722.
99. Smalley RE. Self-assembly of the fullerenes. Acc Chem Res 1992, 25:98-105.
100. Zhang QL, O'Brien SC, Heath JR, Liu Y, Kroto HW, Smalley RE. Reactivity of large carbon clusters: Spheroidal carbon shells and their possible relevance to the formation and morphology of soot. J Phys Chem 1986, 90:525-528.
101. von Helden G, Gotts NG, Bowers MT. Experimental evidence for the formation of fullerenes by collisional heating of carbon rings in the gas phase. Nature 1993, 363:60-63.
102. Goroff NS. Mechanism of fullerene formation. Acc Chem Res 1996, 29:77-83.
103. 60 formation puzzle 'Solved': QM/MD simulations reveal the shrinking hot giant road of the dynamic fullerene self-assembly mechanism. J Phys Chem B 2006, 110:14531-14545.
104. 84 fullerene isomers. Chem Phys Lett 2005, 412:210-216.
105. 2 molecules to fullerenes in quantum chemical molecular dynamics. Nano Lett 2003, 3:1657-1664.
106. Ueno Y, Saito S. Geometries, stabilities, and reactions of carbon clusters: towards a microscopic theory of fullerene formation. Phys Rev B 2008, 77:085403/085401-085411.
107. Xu CX, Scuseria GE. Tight-binding molecular dynamics simulations of fullerene annealing and fragmentation. Phys Rev Lett 1994, 72:669-672.
108. 2 carbon clusters and cluster-assembled solids. New J Phys 2005, 7:1-8.
109. Johnson MP, Donnet JB, Wang TK, Wang CC, Locke RW, et al. A dynamic continuum of nanostructured carbons in the combustion furnace. Carbon 2002, 40:189-194.
110. Zheng G, Wang Z, Irle S, Morokuma K. Quantum chemical molecular dynamics simulations of 'Shrinking' of hot giant fullerenes. J Nanosci Nanotechnol 2007, 7:1662-1669.
111. Taylor R, ed. The Chemistry of Fullerenes. Singapore: World Scientific Publishing; 1995.
112. Langa F, Nierengarten JF, eds. Fullerenes: Principles and Applications. Cambridge: Royal Society of Chemistry; 2007.
113. Kadish KM, Ruoff RS, eds. Fullerenes: Chemistry, Physics and Technology. New York: John Wiley & Sons; 2000.
114. Akasaka T, Nagase S, eds. Endofullerenes: A new family of carbon clusters. Dordrecht: Kluwer Academic Publishers; 2002.
115. Martin N. New challenges in fullerene chemistry. Chem Commun 2006:2093-2104.
116. Chen Z, King RB. Spherical aromaticity: recent work on fullerenes, polyhedral boranes, and related structures. Chem Rev 2005, 105:3613-3642.