中文
Earlier issues
Announcement
More
Progress in Chemistry 2011, Vol. 23 Issue (01): 53-64 Previous Articles   Next Articles

• Invited Article •

Synthetic Chemistry of Fullerenes

Deng Shunliu1, Xie Suyuan1,2   

  1. 1. Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China;
    2. State Key Laboratory for Physical Chemistry of Solid Surfaces, Xiamen University, Xiamen 361005, China
  • Received: Revised: Online: Published:
PDF ( 1696 ) Cited
Export

EndNote

Ris

BibTeX

Fullerenes are a class of cage-like molecules made of hexagons and exactly twelve pentagons. Since the discovery of fullerene in the middle of 1980’s, the chemistry of fullerenes has become a flourishing field as a result of their unique structures and remarkable properties. In the past twenty-five years, significant progress has been achieved in both fundamental and practical fields. Efforts have been made to improve synthetic efficiency and to synthesize new species of fullerene cage. Herein we review the methods for fullerene synthesis and the novel cage geometries (more than 60 fullerene structures) that have been retrieved and characterized to date. Advances in the production, separation and characterization of various fullerenes are presented, including hollow fullerenes, endohedral fullerenes, exohedral derivatives of fullerenes and azafullerenes.

Key words: fullerenes, synthesis, structure, endohedral fullerenes, exohedral derivatization, IPR, azafullerenes

CLC Number: 

[1] Kroto H W, Heath J R, O'Brien S C, Curl R F, Smalley R E. Nature, 1985, 318(6042): 162—163
[2] Kratschmer W, Lamb L D, Fostiropoulos K, Huffman D R. Nature, 1990, 347(6291): 354—358
[3] Haufler R E, Conceicao J, Chibante L P F, Chai Y, Byrne N E, Flanagan S, Haley M M, O'Brien S C, Smalley R E, Pan C, et al. J. Phys. Chem., 1990, 94(24): 8634—8636
[4] Tohji K, Paul A, Moro L, Malhotra R, Lorents D C, Ruoff R S. J. Phys. Chem., 1995, 99(50): 17785—17788
[5] Chai Y, Guo T, Jin C, Haufler R E, Chibante L P F, Fure J, Wang L, Alford J M, Smalley R E. J. Phys. Chem., 1991, 95(20): 7564—7568
[6] Xie S Y, Huang R B, Ding J, Yu L J, Wang Y H, Zheng L S. J. Phys. Chem. A, 2000, 104(31): 7161—7164
[7] Chibante L P F, Thess A, Alford J M, Diener M D, Smalley R E. J. Phys. Chem., 1993, 97(34): 8696—8700
[8] Fields C L, Pitts J R, Hale M J, Bingham C, Lewandowski A, King D E. J. Phys. Chem., 1993, 97(34): 8701—8702
[9] Laplaze D, Bernier P, Flamant G, Lebrun M, Brunelle A, Della-Negra S. Synth. Met., 1996, 77(1/3): 67—71
[10] Gerhardt P, Loeffler S, Homann K H. Chem. Phys. Lett., 1987, 137(4): 306—310
[11] Howard J B, McKinnon J T, Makarovsky Y, Lafleur A L, Johnson M E. Nature, 1991, 352(6331): 139—141
[12] Gao Z Y, Jiang W S, Sun D, Xie S Y, Huang R B, Zheng L S. Combust. Flame, 2010, 157(5): 966—969
[13] Murayama H, Tomonoh S, Alford J M, Karpuk M E. Fullerenes, Nanotubes, Carbon Nanostruct., 2004, 12(1 & 2): 1—9
[14] Chang T M, Naim A, Ahmed S N, Goodloe G, Shevlin P B. J. Am. Chem. Soc., 1992, 114(19): 7603—7604
[15] Taylor R, Langley G J, Kroto H W, Walton D R M. Nature, 1993, 366(6457): 728—731
[16] Xie S Y, Huang R B, Yu L J, Ding J, Zheng L S. Appl. Phys. Lett., 1999, 75(18): 2764—2766
[17] Xie S Y, Huang R B, Deng S L, Yu L J, Zheng L S. J. Phys. Chem. B, 2001, 105(9): 1734—1738
[18] Rubin Y, Parker T C, Khan S I, Holliman C L, McElvany S W. J. Am. Chem. Soc., 1996, 118(22): 5308—5309
[19] Tobe Y, Nakagawa N, Naemura K, Wakabayashi T, Shida T, Achiba Y. J. Am. Chem. Soc., 1998, 120(18): 4544—4545
[20] Tobe Y, Nakagawa N, Kishi J Y, Sonoda M, Naemura K, Wakabayashi T, Shida T, Achiba Y. Tetrahedron, 2001, 57(17): 3629—3636
[21] Scott L T, Boorum M M, McMahon B J, Hagen S, Mack J, Blank J, Wegner H, de Meijere A. Science, 2002, 295(5559): 1500—1503
[22] Amsharov K Y, Jansen M. J. Org. Chem., 2008, 73(7): 2931—2934
[23] Amsharov K, Jansen M. Chem. Commun., 2009, 2691—2693
[24] Otero G, Biddau G, Sanchez-Sanchez C, Caillard R, Lopez M F, Rogero C, Palomares F J, Cabello N, Basanta M A, Ortega J, Mendez J, Echavarren A M, Perez R, Gomez-Lor B, Martin-Gago J A. Nature, 2008, 454(7206): 865—868
[25] Kroto H W. Nature, 1987, 329(6139): 529—531
[26] Rohlfing E A, Cox D M, Kaldor A. J. Chem. Phys., 1984, 81(7): 3322—3330
[27] Smalley R E. Acc. Chem. Res., 1992, 25(3): 98—105
[28] Ewels C P. Nano Lett., 2006, 6(5): 890—895
[29] Heath J R, O'Brien S C, Zhang Q, Liu Y, Curl R F, Tittel F K, Smalley R E. J. Am. Chem. Soc., 1985, 107(25): 7779—7780
[30] Paquette L A, Ternansky R J, Balogh D W. J. Am. Chem. Soc., 1982, 104(16): 4502—4503
[31] Ternansky R J, Balogh D W, Paquette L A. J. Am. Chem. Soc., 1982, 104(16): 4503—4504
[32] Prinzbach H, Weller A, Landenberger P, Wahl F, Worth J, Scott L T, Gelmont M, Olevano D, von Issendorff B. Nature, 2000, 407(6800): 60—63
[33] Wahl F, Weiler A, Landenberger P, Sackers E, Voss T, Haas A, Lieb M, Hunkler D, Woerth J, Knothe L, Prinzbach H. Chem. Eur. J., 2006, 12(24): 6255—6267
[34] Piskoti C, Yarger J, Zettl A. Nature, 1998, 393(6687): 771—774
[35] Koshio A, Inakuma M, Sugai T, Shinohara H. J. Am. Chem. Soc., 2000, 122(2): 398—399
[36] Koshio A, Inakuma M, Wang Z W, Sugai T, Shinohara H. J. Phys. Chem. B, 2000, 104(33): 7908—7913
[37] Xie S Y, Gao F, Lu X, Huang R B, Wang C R, Zhang X, Liu M L, Deng S L, Zheng L S. Science, 2004, 304(5671): 699
[38] Tan Y Z, Li J, Zhu F, Han X, Jiang W S, Huang R B, Zheng Z, Qian Z Z, Chen R T, Liao Z J, Xie S Y, Lu X, Zheng L S. Nat. Chem., 2010, 2(4): 269—273
[39] Tan Y Z, Han X, Wu X, Meng Y Y, Zhu F, Qian Z Z, Liao Z J, Chen M H, Lu X, Xie S Y, Huang R B, Zheng L S. J. Am. Chem. Soc., 2008, 130(46): 15240—15241
[40] Troshin P A, Avent A G, Darwish A D, Martsinovich N, Abdul-Sada A K, Street J M, Taylor R. Science, 2005, 309(5732): 278—281
[41] Hummelen J C, Knight B, Pavlovich J, Gonzalez R, Wudl F. Science, 1995, 269(5230): 1554—1556
[42] Zhang G, Huang S, Xiao Z, Chen Q, Gan L, Wang Z. J. Am. Chem. Soc., 2008, 130(38): 12614—12615
[43] Tan Y Z, Liao Z J, Qian Z Z, Chen R T, Wu X, Liang H, Han X, Zhu F, Zhou S J, Zheng Z, Lu X, Xie S Y, Huang R B, Zheng L S. Nat. Mater., 2008, 7(10): 790—794
[44] Qian W, Bartberger M D, Pastor S J, Houk K N, Wilkins C L, Rubin Y. J. Am. Chem. Soc., 2000, 122(34): 8333—8334
[45] Qian W, Chuang S C, Amador R B, Jarrosson T, Sander M, Pieniazek S, Khan S I, Rubin Y. J. Am. Chem. Soc., 2003, 125(8): 2066—2067
[46] Wang C R, Shi Z Q, Wan L J, Lu X, Dunsch L, Shu C Y, Tang Y L, Shinohara H. J. Am. Chem. Soc., 2006, 128(20): 6605—6610
[47] Han X, Zhou S J, Tan Y Z, Wu X, Gao F, Liao Z J, Huang R B, Feng Y Q, Lu X, Xie S Y, Zheng L S. Angew. Chem. Int. Ed., 2008, 47(29): 5340—5343
[48] Wang C R, Kai T, Tomiyama T, Yoshida T, Kobayashi Y, Nishibori E, Takata M, Sakata M, Shinohara H. Nature, 2000, 408(6811): 426—427
[49] Stevenson S, Fowler P W, Heine T, Duchamp J C, Rice G, Glass T, Harich K, Hajdu E, Bible R, Dorn H C. Nature, 2000, 408(6811): 427—428
[50] Olmstead M M, Lee H M, Duchamp J C, Stevenson S, Marciu D, Dorn H C, Balch A L. Angew. Chem. Int. Ed., 2003, 42(8): 900—903
[51] Shi Z Q, Wu X, Wang C-R, Lu X, Shinohara H. Angew. Chem. Int. Ed., 2006, 45(13): 2107—2111
[52] Yang S, Popov A A, Dunsch L. Angew. Chem., Int. Ed. 2007, 46(8): 1256—1259
[53] Kato H, Taninaka A, Sugai T, Shinohara H. J. Am. Chem. Soc., 2003, 125(26): 7782—7783
[54] Lu X, Nikawa H, Nakahodo T, Tsuchiya T, Ishitsuka M O, Maeda Y, Akasaka T, Toki M, Sawa H, Slanina Z, Mizorogi N, Nagase S. J. Am. Chem. Soc., 2008, 130(28): 9129—9136
[55] Lu X, Nikawa H, Tsuchiya T, Maeda Y, Ishitsuka M O, Akasaka T, Toki M, Sawa H, Slanina Z, Mizorogi N, Nagase S. Angew. Chem. Int. Ed., 2008, 47(45): 8642—8645
[56] Wakahara T, Nikawa H, Kikuchi T, Nakahodo T, Rahman G M A, Tsuchiya T, Maeda Y, Akasaka T, Yoza K, Horn E, Yamamoto K, Mizorogi N, Slanina Z, Nagase S. J. Am. Chem. Soc., 2006, 128(44): 14228—14229
[57] Diener M D, Alford J M. Nature, 1998, 393(6686): 668—671
[58] Ettl R, Chao I, Diederich F, Whetten R L. Nature, 1991, 353(6340): 149—153
[59] Shustova N B, Kuvychko I V, Bolskar R D, Seppelt K, Strauss S H, Popov A A, Boltalina O V. J. Am. Chem. Soc., 2006, 128(49): 15793—15798
[60] Ioffe I N, Goryunkov A A, Tamm N B, Sidorov L N, Kemnitz E, Troyanov S I. Angew. Chem. Int. Ed., 2009, 48(32): 5904—5907
[61] Yang S, Popov A A, Dunsch L. J. Phys. Chem. B, 2007, 111(49): 13659—13663
[62] Diederich F, Whetten R L, Thilgen C, Ettl R, Chao I, Alvarez M M. Science, 1991, 254(5039): 1768—1770
[63] Kikuchi K, Nakahara N, Wakabayashi T, Suzuki S, Shiromaru H, Miyake Y, Saito K, Ikemoto I, Kainosho M, Achiba Y. Nature, 1992, 357(6374): 142—145
[64] Shustova N B, Newell B S, Miller S M, Anderson O P, Bolskar R D, Seppelt K, Popov A A, Boltalina O V, Strauss S H. Angew. Chem. Int. Ed., 2007, 46(22): 4111—4114
[65] Tan Y Z, Li J, Zhou T, Feng Y Q, Lin S C, Lu X, Zhan Z P, Xie S Y, Huang R B, Zheng L S. J. Am. Chem. Soc., 2010, 132(36): 12648—12652
[66] Popov A A, Krause M, Yang S, Wong J, Dunsch L. J. Phys. Chem. B, 2007, 111(13): 3363—3369
[67] Beavers C M, Chaur M N, Olmstead M M, Echegoyen L, Balch A L. J. Am. Chem. Soc., 2009, 131(32): 11519—11524
[68] Zuo T, Xu L, Beavers C M, Olmstead M M, Fu W, Crawford T D, Balch A L, Dorn H C. J. Am. Chem. Soc., 2008, 130(39): 12992—12997
[69] Wang C R, Sugai T, Kai T, Tomiyama T, Shinohara H. Chem. Commun., 2000, 557—558
[70] Stevenson S, Rice G, Glass T, Harlch K, Cromer F, Jordan M R, Craft J, Hadju E, Bible R, Olmstead M M, Maltra K, Fisher A J, Balch A L, Dorn H C. Nature, 1999, 401(6748): 55—57
[71] Iiduka Y, Wakahara T, Nakahodo T, Tsuchiya T, Sakuraba A, Maeda Y, Akasaka T, Yoza K, Horn E, Kato T, Liu M T H, Mizorogi N, Kobayashi K, Nagase S. J. Am. Chem. Soc., 2005, 127(36): 12500—12501
[72] Zuo T, Olmstead M M, Beavers C M, Balch A L, Wang G, Yee G T, Shu C, Xu L, Elliott B, Echegoyen L, Duchamp J C, Dorn H C. Inorg. Chem., 2008, 47(12): 5234—5244
[73] Nikawa H, Yamada T, Cao B, Mizorogi N, Slanina Z, Tsuchiya T, Akasaka T, Yoza K, Nagase S. J. Am. Chem. Soc., 2009, 131(31): 10950—10954
[74] Akasaka T, Wakahara T, Nagase S, Kobayashi K, Waelchli M, Yamamoto K, Kondo M, Shirakura S, Okubo S, Maeda Y, Kato T, Kako M, Nakadaira Y, Nagahata R, Gao X, van Caemelbecke E, Kadish K M. J. Am. Chem. Soc., 2000, 122(38): 9316—9317
[75] Feng L, Tsuchiya T, Wakahara T, Nakahodo T, Piao Q, Maeda Y, Akasaka T, Kato T, Yoza K, Horn E, Mizorogi N, Nagase S. J. Am. Chem. Soc., 2006, 128(18): 5990—5991
[76] Akasaka T, Wakahara T, Nagase S, Kobayashi K, Waelchli M, Yamamoto K, Kondo M, Shirakura S, Maeda Y, Kato T, Kako M, Nakadaira Y, Gao X, van Caemelbecke E, Kadish K M. J. Phys. Chem. B, 2001, 105(15): 2971—2974
[77] Olmstead M M, de Bettencourt-Dias A, Stevenson S, Dorn H C, Balch A L. J. Am. Chem. Soc., 2002, 124(16): 4172—4173
[78] Olmstead M M, Lee H M, Stevenson S, Dorn H C, Balch A L. Chem. Commun., 2002, 2688—2689
[79] Mercado B Q, Beavers C M, Olmstead M M, Chaur M N, Walker K, Holloway B C, Echegoyen L, Balch A L. J. Am. Chem. Soc., 2008, 130(25): 7854—7855
[80] Tagmatarchis N, Avent A G, Prassides K, Dennis T J S, Shinohara H. Chem. Commun., 1999, 1023—1024
[81] Tamm N B, Sidorov L N, Kemnitz E, Troyanov S I. Chem. Eur. J., 2009, 15(40): 10486—10492
[82] Wang C—R, Kai T, Tomiyama T, Yoshida T, Kobayashi Y, Nishibori E, Takata M, Sakata M, Shinohara H. Angew. Chem. Int. Ed., 2001, 40(2): 397—399
[83] Dennis T J S, Kai T, Tomiyama T, Shinohara H. Chem. Commun., 1998, 619—620
[84] Ioffe I N, Chen C, Yang S, Sidorov L N, Kemnitz E, Troyanov S I. Angew. Chem. Int. Ed., 2010, 49(28): 4784—4787
[85] Beavers C M, Zuo T, Duchamp J C, Harich K, Dorn H C, Olmstead M M, Balch A L. J. Am. Chem. Soc., 2006, 128(35): 11352—11353
[86] Zuo T, Walker K, Olmstead M M, Melin F, Holloway B C, Echegoyen L, Dorn H C, Chaur M N, Chancellor C J, Beavers C M, Balch A L, Athans A J. Chem. Commun., 2008, 1067—1069
[87] Sun G, Kertesz M. Chem. Phys., 2002, 276(2): 107—114
[88] Zuo T, Beavers C M, Duchamp J C, Campbell A, Dorn H C, Olmstead M M, Balch A L. J. Am. Chem. Soc., 2007, 129(7): 2035—2043
[89] Troyanov S I, Tamm N B. Chem. Commun., 2009, 6035—6037
[90] Yang H, Beavers C M, Wang Z, Jiang A, Liu Z, Jin H, Mercado B Q, Olmstead M M, Balch A L. Angew. Chem. Int. Ed., 2010, 49(5): 886—890
[91] Kareev I E, Popov A A, Kuvychko I V, Shustova N B, Lebedkin S F, Bubnov V P, Anderson O P, Seppelt K, Strauss S H, Boltalina O V. J. Am. Chem. Soc., 2008, 130(40): 13471—13489
[92] Kemnitz E, Troyanov S I. Angew. Chem. Int. Ed., 2009, 48(14): 2584—2587
[93] Tagmatarchis N, Arcon D, Prato M, Shinohara H. Chem. Commun., 2002, 2992—2993
[94] Yang H, Lu C, Liu Z, Jin H, Che Y, Olmstead M M, Balch A L. J. Am. Chem. Soc., 2008, 130(51): 17296—17300
[95] Che Y, Yang H, Wang Z, Jin H, Liu Z, Lu C, Zuo T, Dorn H C, Beavers C M, Olmstead M M, Balch A L. Inorg. Chem., 2009, 48(13): 6004—6010
[96] Tamm N B, Sidorov L N, Kemnitz E, Troyanov S I. Angew. Chem. Int. Ed., 2009, 48(48): 9102—9104
[97] Mercado B Q, Jiang A, Yang H, Wang Z, Jin H, Liu Z, Olmstead M M, Balch A L. Angew. Chem. Int. Ed., 2009, 48(48): 9114—9116
[98] Akasaka T, Nagase S, Kobayashi K, Walchli M, Yamamoto K, Funasaka H, Kako M, Hoshino T, Erata T. Angew. Chem., Int. Ed. Engl., 1997, 36(15): 1643—1645
[99] Aoyagi S, Nishibori E, Sawa H, Sugimoto K, Takata M, Miyata Y, Kitaura R, Shinohara H, Okada H, Sakai T, Ono Y, Kawachi K, Yokoo K, Ono S, Omote K, Kasama Y, Ishikawa S, Komuro T, Tobita H. Nat. Chem., 2010, 2(8): 678—683
[100] Nikawa H, Kikuchi T, Wakahara T, Nakahodo T, Tsuchiya T, Rahman G M A, Akasaka T, Maeda Y, Yoza K, Horn E, Yamamoto K, Mizorogi N, Nagase S. J. Am. Chem. Soc., 2005, 127(27): 9684—9685
[101] Wang C R, Kai T, Tomiyama T, Yoshida T, Kobayashi Y, Nishibori E, Takata M, Sakata M, Shinohara H. Nature, 2000, 408(6811): 426—427
[102] Yang S, Dunsch L. J. Phys. Chem. B, 2005, 109(25): 12320—12328
[103] Yang S, Dunsch L. Chem. Eur. J., 2006, 12(2): 413—419
[104] Yang S, Troyanov S I, Popov A A, Krause M, Dunsch L. J. Am. Chem. Soc., 2006, 128(51): 16733—16739
[105] Wang T S, Chen N, Xiang J F, Li B, Wu J Y, Xu W, Jiang L, Tan K, Shu C Y, Lu X, Wang C R. J. Am. Chem. Soc., 2009, 131(46): 16646—16647
[106] Iiduka Y, Wakahara T, Nakajima K, Tsuchiya T, Nakahodo T, Maeda Y, Akasaka T, Mizorogi N, Nagase S. Chem. Commun., 2006, 19): 2057—2059
[107] Inoue T, Tomiyama T, Sugai T, Okazaki T, Suematsu T, Fujii N, Utsumi H, Nojima K, Shinohara H. J. Phys. Chem. B, 2004, 108(23): 7573—7579
[108] Shinohara H, Inakuma M, Hayashi N, Sato H, Saito Y, Kato T, Bandow S. J. Phys. Chem., 1994, 98(35): 8597—8599
[109] Stevenson S, Mackey M A, Stuart M A, Phillips J P, Easterling M L, Chancellor C J, Olmstead M M, Balch A L. J. Am. Chem. Soc., 2008, 130(36): 11844—11845
[110] Mercado B Q, Olmstead M M, Beavers C M, Easterling M L, Stevenson S, Mackey M A, Coumbe C E, Phillips J D, Phillips J P, Poblet J M, Balch A L. Chem. Commun., 2010, 279—281
[111] Krause M, Ziegs F, Popov A A, Dunsch L. ChemPhysChem, 2007, 8(4): 537—540
[112] Dunsch L, Yang S, Zhang L, Svitova A, Oswald S, Popov A A. J. Am. Chem. Soc., 2010, 132(15): 5413—5421
[113] Chen N, Chaur M N, Moore C, Pinzon J R, Valencia R, Rodriguez-Fortea A, Poblet J M, Echegoyen L. Chem. Commun., 2010, 4818—4820
[114] Yang S, Chen C, Popov A A, Zhang W, Liu F, Dunsch L. Chem. Commun., 2009, 6391—6393
[115] Weng Q H, He Q, Liu T, Huang H Y, Chen J H, Gao Z Y, Xie S Y, Lu X, Huang R B, Zheng L S. J. Am. Chem. Soc., 2010, ASAP
[116] Pradeep T, Vijayakrishnan V, Santra A K, Rao C N R. J. Phys. Chem., 1991, 95(26): 10564—10565
[117] Averdung J, Luftmann H, Schlachter I, Mattay J. Tetrahedron, 1995, 51(25): 6977—6982
[118] Lamparth I, Nuber B, Schick G, Skiebe A, Groesser T, Hirsch A. Angew. Chem. Int. Ed. Engl., 1995, 34(20): 2257—2259
[119] Hasharoni K, Bellavia-Lund C, KeshavarzK M, Srdanov G, Wudl F. J. Am. Chem. Soc., 1997, 119(45): 11128—11129
[120] Nuber B, Hirsch A. Chem. Commun., 1996, 1421—1422
[121] Tagmatarchis N, Okada K, Tomiyama T, Shinohara H. Synlett., 2000, 1761—1764 Science, 1995, 269(5230): 1554—1556

[42] Zhang G, Huang S, Xiao Z, Chen Q, Gan L, Wang Z. J. Am. Chem. Soc., 2008, 130(38): 12614—12615

[43] Tan Y Z, Liao Z J, Qian Z Z, Chen R T, Wu X, Liang H, Han X, Zhu F, Zhou S J, Zheng Z, Lu X, Xie S Y, Huang R B, Zheng L S. Nat. Mater., 2008, 7(10): 790—794

[44] Qian W, Bartberger M D, Pastor S J, Houk K N, Wilkins C L, Rubin Y. J. Am. Chem. Soc., 2000, 122(34): 8333—8334

[45] Qian W, Chuang S C, Amador R B, Jarrosson T, Sander M, Pieniazek S, Khan S I, Rubin Y. J. Am. Chem. Soc., 2003, 125(8): 2066—2067

[46] Wang C R, Shi Z Q, Wan L J, Lu X, Dunsch L, Shu C Y, Tang Y L, Shinohara H. J. Am. Chem. Soc., 2006, 128(20): 6605—6610

[47] Han X, Zhou S J, Tan Y Z, Wu X, Gao F, Liao Z J, Huang R B, Feng Y Q, Lu X, Xie S Y, Zheng L S. Angew. Chem., Int. Ed., 2008, 47(29): 5340—5343

[48] Wang C R, Kai T, Tomiyama T, Yoshida T, Kobayashi Y, Nishibori E, Takata M, Sakata M, Shinohara H. Nature, 2000, 408(6811): 426—427

[49] Stevenson S, Fowler P W, Heine T, Duchamp J C, Rice G, Glass T, Harich K, Hajdu E, Bible R, Dorn H C. Nature, 2000, 408(6811): 427—428

[50] Olmstead M M, Lee H M, Duchamp J C, Stevenson S, Marciu D, Dorn H C, Balch A L. Angew. Chem. Int. Ed., 2003, 42(8): 900—903

[51] Shi Z Q, Wu X, Wang C-R, Lu X, Shinohara H. Angew. Chem., Int. Ed., 2006, 45(13): 2107—2111

[52] Yang S, Popov A A, Dunsch L. Angew. Chem., Int. Ed. 2007, 46(8): 1256—1259

[53] Kato H, Taninaka A, Sugai T, Shinohara H. J. Am. Chem. Soc., 2003, 125(26): 7782—7783

[54] Lu X, Nikawa H, Nakahodo T, Tsuchiya T, Ishitsuka M O, Maeda Y, Akasaka T, Toki M, Sawa H, Slanina Z, Mizorogi N, Nagase S. J. Am. Chem. Soc., 2008, 130(28): 9129—9136

[55] Lu X, Nikawa H, Tsuchiya T, Maeda Y, Ishitsuka M O, Akasaka T, Toki M, Sawa H, Slanina Z, Mizorogi N, Nagase S. Angew. Chem. Int. Ed., 2008, 47(45): 8642—8645

[56] Wakahara T, Nikawa H, Kikuchi T, Nakahodo T, Rahman G M A, Tsuchiya T, Maeda Y, Akasaka T, Yoza K, Horn E, Yamamoto K, Mizorogi N, Slanina Z, Nagase S. J. Am. Chem. Soc., 2006, 128(44): 14228—14229

[57] Diener M D, Alford J M. Nature, 1998, 393(6686): 668—671

[58] Ettl R, Chao I, Diederich F, Whetten R L. Nature, 1991, 353(6340): 149—153

[59] Shustova N B, Kuvychko I V, Bolskar R D, Seppelt K, Strauss S H, Popov A A, Boltalina O V. J. Am. Chem. Soc., 2006, 128(49): 15793—15798

[60] Ioffe I N, Goryunkov A A, Tamm N B, Sidorov L N, Kemnitz E, Troyanov S I. Angew. Chem. Int. Ed., 2009, 48(32): 5904—5907

[61] Yang S, Popov A A, Dunsch L. J. Phys. Chem. B, 2007, 111(49): 13659—13663

[62] Diederich F, Whetten R L, Thilgen C, Ettl R, Chao I, Alvarez M M. Science, 1991, 254(5039): 1768—1770

[63] Kikuchi K, Nakahara N, Wakabayashi T, Suzuki S, Shiromaru H, Miyake Y, Saito K, Ikemoto I, Kainosho M, Achiba Y. Nature, 1992, 357(6374): 142—145

[64] Shustova N B, Newell B S, Miller S M, Anderson O P, Bolskar R D, Seppelt K, Popov A A, Boltalina O V, Strauss S H. Angew. Chem. Int. Ed., 2007, 46(22): 4111—4114

[65] Tan Y Z, Li J, Zhou T, Feng Y Q, Lin S C, Lu X, Zhan Z P, Xie S Y, Huang R B, Zheng L S. J. Am. Chem. Soc., 2010, 132(36): 12648—12652

[66] Popov A A, Krause M, Yang S, Wong J, Dunsch L. J. Phys. Chem. B, 2007, 111(13): 3363—3369

[67] Beavers C M, Chaur M N, Olmstead M M, Echegoyen L, Balch A L. J. Am. Chem. Soc., 2009, 131(32): 11519—11524

[68] Zuo T, Xu L, Beavers C M, Olmstead M M, Fu W, Crawford T D, Balch A L, Dorn H C. J. Am. Chem. Soc., 2008, 130(39): 12992—12997

[69] Wang C R, Sugai T, Kai T, Tomiyama T, Shinohara H. Chem. Commun., 2000, 557—558

[70] Stevenson S, Rice G, Glass T, Harlch K, Cromer F, Jordan M R, Craft J, Hadju E, Bible R, Olmstead M M, Maltra K, Fisher A J, Balch A L, Dorn H C. Nature, 1999, 401(6748): 55—57

[71] Iiduka Y, Wakahara T, Nakahodo T, Tsuchiya T, Sakuraba A, Maeda Y, Akasaka T, Yoza K, Horn E, Kato T, Liu M T H, Mizorogi N, Kobayashi K, Nagase S. J. Am. Chem. Soc., 2005, 127(36): 12500—12501

[72] Zuo T, Olmstead M M, Beavers C M, Balch A L, Wang G, Yee G T, Shu C, Xu L, Elliott B, Echegoyen L, Duchamp J C, Dorn H C. Inorg. Chem., 2008, 47(12): 5234—5244

[73] Nikawa H, Yamada T, Cao B, Mizorogi N, Slanina Z, Tsuchiya T, Akasaka T, Yoza K, Nagase S. J. Am. Chem. Soc., 2009, 131(31): 10950—10954

[74] Akasaka T, Wakahara T, Nagase S, Kobayashi K, Waelchli M, Yamamoto K, Kondo M, Shirakura S, Okubo S, Maeda Y, Kato T, Kako M, Nakadaira Y, Nagahata R, Gao X, van Caemelbecke E, Kadish K M. J. Am. Chem. Soc., 2000, 122(38): 9316—9317

[75] Feng L, Tsuchiya T, Wakahara T, Nakahodo T, Piao Q, Maeda Y, Akasaka T, Kato T, Yoza K, Horn E, Mizorogi N, Nagase S. J. Am. Chem. Soc., 2006, 128(18): 5990—5991

[76] Akasaka T, Wakahara T, Nagase S, Kobayashi K, Waelchli M, Yamamoto K, Kondo M, Shirakura S, Maeda Y, Kato T, Kako M, Nakadaira Y, Gao X, van Caemelbecke E, Kadish K M. J. Phys. Chem. B, 2001, 105(15): 2971—2974

[77] Olmstead M M, de Bettencourt-Dias A, Stevenson S, Dorn H C, Balch A L. J. Am. Chem. Soc., 2002, 124(16): 4172—4173

[78] Olmstead M M, Lee H M, Stevenson S, Dorn H C, Balch A L. Chem. Commun., 2002, 2688—2689

[79] Mercado B Q, Beavers C M, Olmstead M M, Chaur M N, Walker K, Holloway B C, Echegoyen L, Balch A L. J. Am. Chem. Soc., 2008, 130(25): 7854—7855

[80] Tagmatarchis N, Avent A G, Prassides K, Dennis T J S, Shinohara H. Chem. Commun., 1999, 1023—1024

[81] Tamm N B, Sidorov L N, Kemnitz E, Troyanov S I. Chem. Eur. J., 2009, 15(40): 10486—10492

[82] Wang C—R, Kai T, Tomiyama T, Yoshida T, Kobayashi Y, Nishibori E, Takata M, Sakata M, Shinohara H. Angew. Chem. Int. Ed., 2001, 40(2): 397—399

[83] Dennis T J S, Kai T, Tomiyama T, Shinohara H. Chem. Commun., 1998, 619—620

[84] Ioffe I N, Chen C, Yang S, Sidorov L N, Kemnitz E, Troyanov S I. Angew. Chem. Int. Ed., 2010, 49(28): 4784—4787

[85] Beavers C M, Zuo T, Duchamp J C, Harich K, Dorn H C, Olmstead M M, Balch A L. J. Am. Chem. Soc., 2006, 128(35): 11352—11353

[86] Zuo T, Walker K, Olmstead M M, Melin F, Holloway B C, Echegoyen L, Dorn H C, Chaur M N, Chancellor C J, Beavers C M, Balch A L, Athans A J. Chem. Commun., 2008, 1067—1069

[87] Sun G, Kertesz M. Chem. Phys., 2002, 276(2): 107—114

[88] Zuo T, Beavers C M, Duchamp J C, Campbell A, Dorn H C, Olmstead M M, Balch A L. J. Am. Chem. Soc., 2007, 129(7): 2035—2043

[89] Troyanov S I, Tamm N B. Chem. Commun., 2009, 6035—6037

[90] Yang H, Beavers C M, Wang Z, Jiang A, Liu Z, Jin H, Mercado B Q, Olmstead M M, Balch A L. Angew. Chem. Int. Ed., 2010, 49(5): 886—890

[91] Kareev I E, Popov A A, Kuvychko I V, Shustova N B, Lebedkin S F, Bubnov V P, Anderson O P, Seppelt K, Strauss S H, Boltalina O V. J. Am. Chem. Soc., 2008, 130(40): 13471—13489

[92] Kemnitz E, Troyanov S I. Angew. Chem. Int. Ed., 2009, 48(14): 2584—2587

[93] Tagmatarchis N, Arcon D, Prato M, Shinohara H. Chem. Commun., 2002, 2992—2993

[94] Yang H, Lu C, Liu Z, Jin H, Che Y, Olmstead M M, Balch A L. J. Am. Chem. Soc., 2008, 130(51): 17296—17300

[95] Che Y, Yang H, Wang Z, Jin H, Liu Z, Lu C, Zuo T, Dorn H C, Beavers C M, Olmstead M M, Balch A L. Inorg. Chem., 2009, 48(13): 6004—6010

[96] Tamm N B, Sidorov L N, Kemnitz E, Troyanov S I. Angew. Chem. Int. Ed., 2009, 48(48): 9102—9104

[97] Mercado B Q, Jiang A, Yang H, Wang Z, Jin H, Liu Z, Olmstead M M, Balch A L. Angew. Chem. Int. Ed., 2009, 48(48): 9114—9116

[98] Akasaka T, Nagase S, Kobayashi K, Walchli M, Yamamoto K, Funasaka H, Kako M, Hoshino T, Erata T. Angew. Chem., Int. Ed. Engl., 1997, 36(15): 1643—1645

[99] Aoyagi S, Nishibori E, Sawa H, Sugimoto K, Takata M, Miyata Y, Kitaura R, Shinohara H, Okada H, Sakai T, Ono Y, Kawachi K, Yokoo K, Ono S, Omote K, Kasama Y, Ishikawa S, Komuro T, Tobita H. Nat. Chem., 2010, 2(8): 678—683

[100] Nikawa H, Kikuchi T, Wakahara T, Nakahodo T, Tsuchiya T, Rahman G M A, Akasaka T, Maeda Y, Yoza K, Horn E, Yamamoto K, Mizorogi N, Nagase S. J. Am. Chem. Soc., 2005, 127(27): 9684—9685

[101] Wang C R, Kai T, Tomiyama T, Yoshida T, Kobayashi Y, Nishibori E, Takata M, Sakata M, Shinohara H. Nature, 2000, 408(6811): 426—427

[102] Yang S, Dunsch L. J. Phys. Chem. B, 2005, 109(25): 12320—12328

[103] Yang S, Dunsch L. Chem. Eur. J., 2006, 12(2): 413—419

[104] Yang S, Troyanov S I, Popov A A, Krause M, Dunsch L. J. Am. Chem. Soc., 2006, 128(51): 16733—16739

[105] Wang T S, Chen N, Xiang J F, Li B, Wu J Y, Xu W, Jiang L, Tan K, Shu C Y, Lu X, Wang C R. J. Am. Chem. Soc., 2009, 131(46): 16646—16647

[106] Iiduka Y, Wakahara T, Nakajima K, Tsuchiya T, Nakahodo T, Maeda Y, Akasaka T, Mizorogi N, Nagase S. Chem. Commun., 2006, 19): 2057—2059

[107] Inoue T, Tomiyama T, Sugai T, Okazaki T, Suematsu T, Fujii N, Utsumi H, Nojima K, Shinohara H. J. Phys. Chem. B, 2004, 108(23): 7573—7579

[108] Shinohara H, Inakuma M, Hayashi N, Sato H, Saito Y, Kato T, Bandow S. J. Phys. Chem., 1994, 98(35): 8597—8599

[109] Stevenson S, Mackey M A, Stuart M A, Phillips J P, Easterling M L, Chancellor C J, Olmstead M M, Balch A L. J. Am. Chem. Soc., 2008, 130(36): 11844—11845

[110] Mercado B Q, Olmstead M M, Beavers C M, Easterling M L, Stevenson S, Mackey M A, Coumbe C E, Phillips J D, Phillips J P, Poblet J M, Balch A L. Chem. Commun., 2010, 279—281

[111] Krause M, Ziegs F, Popov A A, Dunsch L. ChemPhysChem, 2007, 8(4): 537—540

[112] Dunsch L, Yang S, Zhang L, Svitova A, Oswald S, Popov A A. J. Am. Chem. Soc., 2010, 132(15): 5413—5421

[113] Chen N, Chaur M N, Moore C, Pinzon J R, Valencia R, Rodriguez-Fortea A, Poblet J M, Echegoyen L. Chem. Commun., 4818—4820

[114] Yang S, Chen C, Popov A A, Zhang W, Liu F, Dunsch L. Chem. Commun., 2009, 6391—6393

[115] Weng Q H, He Q, Liu T, Huang H Y, Chen J H, Gao Z Y, Xie S Y, Lu X, Huang R B, Zheng L S. J. Am. Chem. Soc., 2010, ASAP

[116] Pradeep T, Vijayakrishnan V, Santra A K, Rao C N R. J. Phys. Chem., 1991, 95(26): 10564—10565

[117] Averdung J, Luftmann H, Schlachter I, Mattay J. Tetrahedron, 1995, 51(25): 6977—6982

[118] Lamparth I, Nuber B, Schick G, Skiebe A, Groesser T, Hirsch A. Angew. Chem., Int. Ed. Engl., 1995, 34(20): 2257—2259

[119] Hasharoni K, Bellavia-Lund C, Keshavarz-K M, Srdanov G, Wudl F. J. Am. Chem. Soc., 1997, 119(45): 11128—11129

[120] Nuber B, Hirsch A. Chem. Commun., 1996, 1421—1422

[121] Tagmatarchis N, Okada K, Tomiyama T, Shinohara H. Synlett, 2000, 1761—1764

 
[1] Jing He, Jia Chen, Hongdeng Qiu. Synthesis of Traditional Chinese Medicines-Derived Carbon Dots for Bioimaging and Therapeutics [J]. Progress in Chemistry, 2023, 35(5): 655-682.
[2] Jianfeng Yan, Jindong Xu, Ruiying Zhang, Pin Zhou, Yaofeng Yuan, Yuanming Li. Nanocarbon Molecules — the Fascination of Synthetic Chemistry [J]. Progress in Chemistry, 2023, 35(5): 699-708.
[3] Yan Bao, Jiachen Xu, Ruyue Guo, Jianzhong Ma. High-Sensitivity Flexible Pressure Sensor Based on Micro-Nano Structure [J]. Progress in Chemistry, 2023, 35(5): 709-720.
[4] Yue Yang, Ke Xu, Xuelu Ma. Catalytic Mechanism of Oxygen Vacancy Defects in Metal Oxides [J]. Progress in Chemistry, 2023, 35(4): 543-559.
[5] Xinyue Wang, Kang Jin. Chemical Synthesis of Peptides and Proteins [J]. Progress in Chemistry, 2023, 35(4): 526-542.
[6] Yixue Xu, Shishi Li, Xiaoshuang Ma, Xiaojin Liu, Jianjun Ding, Yuqiao Wang. Surface/Interface Modulation Enhanced Photogenerated Carrier Separation and Transfer of Bismuth-Based Catalysts [J]. Progress in Chemistry, 2023, 35(4): 509-518.
[7] Liu Yvfei, Zhang Mi, Lu Meng, Lan Yaqian. Covalent Organic Frameworks for Photocatalytic CO2 Reduction [J]. Progress in Chemistry, 2023, 35(3): 349-359.
[8] Niu Wenhui, Zhang Da, Zhao Zhengang, Yang Bin, Liang Feng. Development of Na-Based Seawater Batteries: “Key Components and Challenges” [J]. Progress in Chemistry, 2023, 35(3): 407-420.
[9] Yang Guodong, Yuan Gaoqian, Zhang Jingzhe, Wu Jinbo, Li Faliang, Zhang Haijun. Porous Electromagnetic Wave Absorbing Materials [J]. Progress in Chemistry, 2023, 35(3): 445-457.
[10] Jiang Haoyang, Xiong Feng, Qin Mulin, Gao Song, He Liuruyi, Zou Ruqiang. Conductive Phase Change Materials (PCMs) for Electro-to-Thermal Energy Conversion, Storage and Utilization [J]. Progress in Chemistry, 2023, 35(3): 360-374.
[11] Zixuan Liao, Yuhui Wang, Jianping Zheng. Research Advance of Carbon-Dots Based Hydrophilic Room Temperature Phosphorescent Composites [J]. Progress in Chemistry, 2023, 35(2): 263-373.
[12] Xiaojun Liu, Lang Qin, Yanlei Yu. Light-Driven Handedness Inversion of Cholesteric Liquid Crystals [J]. Progress in Chemistry, 2023, 35(2): 247-262.
[13] Xuan Li, Jiongpeng Huang, Yifan Zhang, Lei Shi. 1D Nanoribbons of 2D Materials [J]. Progress in Chemistry, 2023, 35(1): 88-104.
[14] Chao Ji, Tuo Li, Xiaofeng Zou, Lu Zhang, Chunjun Liang. Two-Dimensional Perovskite Photovoltaic Devices [J]. Progress in Chemistry, 2022, 34(9): 2063-2080.
[15] Chunyi Ye, Yang Yang, Xuexian Wu, Ping Ding, Jingli Luo, Xianzhu Fu. Preparation and Application of Palladium-Copper Nano Electrocatalysts [J]. Progress in Chemistry, 2022, 34(9): 1896-1910.
Viewed
Full text


Abstract

Synthetic Chemistry of Fullerenes