Supramolecular Chemistry of Fullerenes: Host Molecules for Fullerenes on the basis of π-π Interaction

Chemistry of Nanocarbons

Volumn , Issue , 2010, Pages 189-213

  Kawase, Takeshi ^a  

^a UNIVERSITY OF HYOGO   (Japan)

Author keywords

'Jaws porphyrins'; Complexes with host molecules based on porphyrin systems; Fullerene supramolecular chemistry; Fullerenes (C60 and C70) extracted from carbon soot using benzene; Host molecule preparation with high affinity to fullerenes; Host molecules of aromatic systems; Host molecules with dimeric or polymeric structures; Modified porphyrins supramolecular structures with fullerene participation; Nature of fullerene supramolecular property

Indexed keywords

EID: 84886172908     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9780470660188.ch7     Document Type: Chapter

References (105)

1. H. W. Kroto, J. R. Heath, S. C. O'Brien, R. F. Curl, and R. E. Smalley, C60: Buckminsterfullerene, Nature, 318, 162-163 (1985).
2. W. Kratchmer, L. D. Lamb, K. Fostiropoulos, and D. R. Huffman, Solid C60: a new form of carbon, Nature, 347, 354-358 (1990).
3. C. L. Raston,In Comprehensive Supramolecular Chemistry; J. L. Atwood, J. E. D. Davies, D. D. Macnicol and F. Vogtle, Eds.; Pergamon; Oxford, vol. 1, p. 777 (1996).
4. F. Diederich and M. Gomez-Lopez, Supramolecular fullerene chemistry, Chem. Soc. Rev., 28, 263-277 (1999).
5. M. J. Hardie and C. L. Raston, Confinement and recognition of icosahedral main group cage molecules: fullerene C60 and o-, m-, p-dicarbadodecacarborane(12), Chem. Commun., 1153-1163 (1999).
6. A. L. Balch and M. M. Olmstead, Reactions of transition metal complexes with fullerenes (C60, C70, etc.) and related materials, Chem. Rev., 98, 2123-2165 (1998).
7. C. A. Reed and R. D. Bolsker, Discrete fulleride anions and fullerenium cations, Chem. Rev., 100, 1075-1120 (2000).
8. K. E. Geckeler, Advanced Macromolecular and Supramolecular Materials and Processes; Ed.; Kluwer Academic/Plenim; New York, 2003.
9. T. Da, Ros and M. Proto, Medicinal chemistry with fullerenes and fullerene derivatives, Chem. Commun., 663-669 (1999).
10. R. V. Bensasson, E. Bienvenue, M. Dellinger, S. Leach and P. Seta, C60 in model biological systems. A visible-UV absorption study of solvent-dependent parameters and solute aggregation, J. Phys. Chem., 98, 3492-3500 (1994).
11. J. Catalan, J. L. Saiz, J. L. Laynez, N. Jagerovic and J. Elguero, The colors of C60 solutions, Angew. Chem. Int. Ed. Engl., 34, 105-107 (1995).
12. Y.-P. Sun, C. E. Bunker and B. Ma, Quantitative studies of ground and excited state charge transfer complexes of fullerenes with N,N-dimethylaniline and N,N-diethylaniline, J. Am. Chem. Soc., 116, 9692-9699 (1994).
13. G. Sarova and M. N. Berberan-Santos, Stable charge-transfer complexes versus contact complexes. Application to the interaction of fullerenes with aromatic hydrocarbons, J. Phys. Chem. B, 108, 17261-17268 (2004).
14. A. Izuoka, T. Tachikawa, T. Sugawara, Y. Suzuki, M. Konno, Y. Saito and H. Shinohara, An X-ray crystallographic analysis of a (BEDT-TTF)2C60 charge-transfer complex, J. Chem. Soc., Chem. Commun., 1472-1473 (1992).
15. F. Diederich, J. Effing, L. Jonas, L. Jullien, T. Plesnivy, H. Ringsdorf, C. Thilgen and D. Weinstein, Angew. Chem. Int. Ed. Engl., 31, 1599-1602 (1992).
16. T. Andersson, K. Nilsson, M. Sundahl, G. Westman and O. Wennerstrom, C60 Embedded in g-cyclodextrin: a water-soluble fullerene, J. Chem. Soc., Chem. Commun., 604-606 (1992).
17. Z. Yoshida, H. Takekuma, S. Takekuma and Y. Matsubara, Molecular recognition of C60 with g-cyclodextrin, Angew. Chem. Int. Ed. Engl., 33, 1597-1599 (1994).
18. A. Ikeda, T. Sue, M. Akiyama, K. Fujioka, T. Shigematsu, Y. Doi, J. Kikuchi, T. Konishi and R. Nakajima, Preparation of highly photosensitizing liposomes with fullerene-doped lipid bilayer using dispersion-controllable molecular exchange reactions, Org. Lett., 10, 4077-4080 (2008).
19. Y. Liu, H.Wang, P. Liang and H.-Y. Zhang, Water-soluble supramolecular fullerene assembly mediated by metallobridged b-cyclodextrins, Angew. Chem. Int. Ed., 43, 2690-2694 (2004).
20. Y. Nishibayashi, M. Saito, S. Uemura, S. Takekuma, H. Takekuma and Z. Yoshida, Buckminsterfullerenes: A non-metal system for nitrogen fixation, Nature, 428, 279 (2004).
21. M. F. Meidine, P. B. Hitchcock, H. W. Kroto, R. Taylor and D. R. M. Walton, Single crystal X-ray structure of benzene-solvated C60, J. Chem. Soc., Chem. Commun., 1534-1537 (1992).
22. L. Balch, V. J. Catalano, J. W. Lee and M. M. Olmstead, Supramolecular Aggregation of an (h2-C60) Iridium complex involving phenyl chelation of the fullerene, J. Am. Chem. Soc., 114, 5455-5457 (1992).
23. H. Suezawa, T.Yoshida, S. Ishihara,Y. Umezawa and M. Nishio, CH/p interactions as disclosed on the fullerene convex surface. A database study, CrystEngComm., 5, 514-518 (2003).
24. E. M.Veen, P. M. Postma, H. T. Jonkman, A. L. Spek and B. L. Feringa, Solid state organization of C60 by inclusion crystallization with triptycenes, Chem. Commun., 1709-1710 (1999).
25. B. Krautler, T. Muller, J. Maynollo, K. Gruber, C. Kratky, P. Ochsenbein, D. Schwarzenbach and H.-B. Burgi, A topochemically controlled, regiospecific fullerene bisfunctionalization, Angew. Chem. Int. Ed. Engl., 35, 1204-1207 (1996).
26. H. Bredenkouer, S. Henne and D. Volkmer, Nanosized ball joints constructed from C60 and tribenzotriquinacene sockets: synthesis, component self-assembly and structural investigations, Chem.-Eur. J., 13, 9931-9938 (2007).
27. P. E. Georghiou, L. N. Dawe, H.-A. Tran, J. Strube, B. Neumann, H.-G. Stammler and D. Kuck, C3v-Symmetrical tribenzotriquinacenes as hosts for C60 and C70 in solution and in the solid state, J. Org. Chem., 73, 9040-9047 (2008).
28. J. L. Atwood, G. A. Koutsantonis and C. L. Raston, Purification of C60 and C70 by selective complexation with calixarenes, Nature, 368, 229-231 (1994);
29. C. L. Raston, J. L. Atwood, P. J. Nichols and I. B. N. Sudria, Supramolecular encapsulation of aggregates of C60, Chem. Commun., 2615-2616 (1996).
30. T. Suzuki, K. Nakashima and S. Shinkai, Very convenient and efficient purification method for fullerene (C60) with 5,11,17,23,29,35,41,47-Octa-tert-butylcalix[8]arene-49,50,51,52,53,54, 55,56-octol, Chem. Lett., 699-702 (1994).
31. J. L. Atwood, L. J. Barbour, C. L. Raston and I. B. N. Sudria, C60 and C70 Compounds in the pincerlike jaws of calix[6]arene, Angew. Chem. Int. Ed., 37, 981-983 (1998).
32. J. L. Atwood, L. J. Barbour, M.W. Heaven and C. L. Raston, Controlling van derWaals contacts in complexes of fullerene C60, Angew. Chem. Int. Ed., 36, 3254-3257 (2003).
33. K. Tsubaki, K. Tanaka, T. Kinoshita and K. Fuji, Complexation of C60 with hexahomooxacalix [3]arenes and supramolecular structures of complexes in the solid state, Chem. Commun., 895-896 (1998).
34. J.W. Steed, P. C. Junk, J. L. Atwood, M. J. Barnes, C. L. Raston and R. S. Burkhalter, Ball and Socket Nanostructures: new supramolecular chemistry based on cyclotriveratrylene, J. Am. Chem. Soc., 116, 10346-10347 (1994).
35. A. Ikeda, Y. Suzuki, M. Yoshimura and S. Shinkai, On the prerequisites for the formation of solution complexes from [60]fullerene and calix[n]arenes: a novel allosteric effect between [60]fullerene and metal cations in calix[n]aryl ester complexes, Tetrahedron, 54, 2497-2508 (1998).
36. L. J. Barbour, G.W. Orr and J. L. Atwood, Supramolecular intercalation ofC60 into a calixarene bilayer-a well-ordered solid-state structure dominated by van der Waals contacts, Chem. Commun., 1439-1450 (1997).
37. T. Haino, M. Yanase and Y. Fukazawa, New supramolecular complex of C60 based on calix[5] arene-Its structure in the crystal and in solution, Angew. Chem. Int. Ed. Engl., 36, 259-260 (1997).
38. P. E. Georghiou, A. H. Tran, S. S. Stroud and D.W. Thompson, Supramolecular complexation studies of [60]Fullerene with calix[4]naphthalenes-a reinvestigation, Tetrahedron, 62, 2036-2044 (2006).
39. S. Mizyed, M. Ashram, D. O. Miller and P. E. Georghiou, Supramolecular complexation of [60] fullerene with hexahomotrioxacalix[3]naphthalenes: a new class of naphthalene-based calixarenes, J. Chem. Soc., Perkin Trans., 2, 1916-1919 (2001).
40. K. Araki, K. Akao, A. Ikeda, T. Suzuki and S. Shinkai, Molecular design of calixarene-based host molecules for inclusion of C60 in solution, Tetrahedron Lett., 37, 73-77 (1996);
41. S. Shinkai and A. Ikeda, Novel interactions of calixarene p-systems with metal ions and fullerenes, Pure Appl. Chem., 71, 275-280 (1999).
42. H. Matsubara, A. Hasegawa, K. Shiwaku, K. Asano, M. Uno, S. Takahashi and K. Yamamoto, Supramolecular inclusion complexes of fullerenes using cyclotriveratrylene derivatives with aromatic pendants, Chem. Lett., 923-924 (1998).
43. J.-F. Nierengarten, L. Oswald, J.-F. Eckert, J.-F. Nicoud and N. Armaroli, Complexation of fullerenes with dendritic cyclotriveratrylene derivatives, Tetrahedron Lett., 40, 5681-5684 (1999).
44. M. Numata, A. Ikeda, C. Fukuhara and S. Shinkai, Dendrimers can act as a host for [60] fullerene, Tetrahedron Lett., 40, 6945-6948 (1999).
45. D. I. Schuster, J. Rosenthal, S. MacMahon, P. D. Jarowski, C. A. Alabi and D. M. Guldi, Formation and photophysics of a stable concave-convex supramolecular complex of C60 and a substituted s-triazine derivative, Chem. Commun., 2538-2539 (2002).
46. M.-X.Wang, X.-H. Zhang and Q.-Y. Zheng, Synthesis, structure, and [60]fullerene complexation properties of azacalix[m]arene[n]pyridines, Angew. Chem. Int. Ed., 43, 838-843 (2004).
47. E.-X. Zhang, D.-X. Wang, Q.-Y. Zheng and M.-X. Wang, Synthesis of large macrocyclic azacalix[n]arenes (n=6-9) and their complexation with fullerenes C60 andC70, Org. Lett., 10, 2565-2568 (2008).
48. L. Stella, A. L. Capodilupo and M. Bietti, A reassessment of the association between azulene and [60]fullerene. Possible pitfalls in the determination of binding constants through fluorescence spectroscopy, Chem. Commun., 4744-4746 (2008).
49. Y. Matsuo and E. Nakamura, Selective multiaddition of organocopper reagents to fullerenes, Chem. Rev., 108, 3016-3028, 2008
50. M. Sawamura, K. Kawai,Y. Matsuo, K. Kanie and E. Nakamura, Stacking of conical molecules with a fullerene apex into polar columns in crystals and liquid crystals, Nature, 419, 702-705 (2002).
51. Y. Matsuo, A. Muramatsu, Y. Kamikawa, T. Kato and E. Nakamura, Synthesis and structural, electrochemical, and stacking properties of conical molecules possessing buckyferrocene on the apex, J. Am. Chem. Soc., 128, 9586-9587 (2006).
52. T. Haino, M. Yanase and Y. Fukazawa, Fullerenes enclosed in bridged calix[5]arenes, Angew. Chem. Int. Ed., 37, 997-998 (1998).
53. J. C. Iglesias-Sanchez, A. Fragoso, J. de Mendoza and P. Prados, Aryl-aryl linked Bi-5,50-p-tertbutylcalix[ 4]arene tweezer for fullerene complexation, Org. Lett., 8, 2571 (2006).
54. J.Wang and C. D. Gutsche, Complexation of fullerenes with bis-calix[n]arenes synthesized by tandem claisen rearangement, J. Am. Chem. Soc., 120, 12226-12231 (1998).
55. H. Matsubara, T. Shimura, A. Hasegawa, M. Semba, K. Asano and K. Yamamoto, Syntheses of novel fullerene tweezers and their supramolecular inclusion complex of C60, Chem. Lett., 1099-1110 (1999).
56. T. Haino, C. Fukunaga and Y. Fukazawa, A new calix[5]arene-based container: selective extraction of higher fullerenes, Org. Lett., 8, 3545-3548 (2006).
57. H. Matsubara, S. Oguri, K. Asano and K. Yamamoto, Syntheses of novel cyclotriveratrylenophane capsules and their supramolecular complexes of fullerenes, Chem. Lett., 431-432 (1999).
58. A. Ikeda, M. Yoshimura, H. Uzdu, C. Fukuhara and S. Shinkai, Inclusion of [60]fullerene in a homooxacalix[3]arene-based dimeric capsules cross-linked by a PdII-pyridine interaction, J. Am. Chem. Soc., 121, 4296-4297 (1999).
59. C. G. Claessens and T. Torres, Inclusion of C60 fullerene in a M3L2 subphthalocyanine cage, Chem. Commun., 1298-1299 (2004).
60. L. Pirondini, D. Bonifazi, B. Cantadori, P. Braiuca, M. Campagnolo, R. D. Zorzi, S. Geremia, F. Diederich and E. Dalcanale, Inclusion of methano[60]fullerene derivatives in cavitand-based coordination cages, Tetrahedron, 62, 2008-2015 (2006).
61. T. Haino, H. Araki, Y. Yamanaka and Y. Fukazawa, Fullerene receptor based on calyx[5]arene through metal-assisted self-assembly, Tetrahedron Lett., 42, 402 (2001).
62. M. Yanase, T. Haino and Y. Fukazawa, A self-assembling molecular container for fullerenes, Tetrahedron Lett., 40, 2781-2784 (1999).
63. E. Huerta, G. A. Metselaar, A. Fragoso, E. Santos, C. Bo and J. de Mendoza, Selective binding and easy separation of C70 by nanoscale self-assembled capsules, Angew. Chem. Int. Ed., 46, 202-205 (2007).
64. G. Dan Pantos, J.-L. Wietor and J. K. M. Sanders, Filling helical nanotubes with C60, Angew. Chem. Int. Ed., 46, 2238-2240 (2007).
65. J.-L. Weitor, G. Dan Pantos and J. K. M. Sanders, Templated amplification of an unexpected receptor for C70, Angew. Chem. Int. Ed., 47, 2689-2692 (2008).
66. T. Kawauchi, J. Kumaki, A. Kitaura, K. Okoshi, H. Kusanagi, K. Kobayashi, T. Sugai, H. Shinohara and E. Yashima, Encapsulation of fullerenes in a helical PMMA cavity leading to a robust processable complex with a macromolecular helicity, Angew. Chem. Int. Ed., 47, 515-519 (2008).
67. T. Kawauchi, A. Kitaura, J. Kumaki, H. Kusanagi and E. Yashima, Helix-sense-controlled synthesis of optically active poly(methyl methacrylate) stereocomplexes, J. Am. Chem. Soc., 130, 11889-11891 (2008).
68. Y. Sun, T. Drovetskaya, R. D. Bolskar, R. Bau, P. D. W. Boyd and C. A. Reed, Fulleride of pyrrolidine-functionalized C60, J. Org. Chem., 62, 3642-3649 (1997).
69. P. D.W. Boyd and C. A. Reed, Fullerene - Porphyrin constructs, Acc. Chem. Res., 38, 235-242 (2005).
70. K. Tashiro, T. Aida, J.-Y. Zheng, K. Kinbara, Saigo, S. Sakamoto and K. Yamaguchi, A cyclic dimer of metalloporphyrin forms a highly stable inclusion complex with C60, J. Am. Chem. Soc., 121, 9477-9478 (1999).
71. M. Shirakawa, N. Fujita, H. Shimakoshi,Y. Hisaeda and S. Shinkai, Molecular programming of organogelators which can accept [60]fullerene by encapsulation, Tetrahedron, 62, 2016-2024 (2006).
72. M. Kimura, Y. Saito, K. Ohta, K. Hanabusa, H. Shirai and N. Kobayashi, Self-organization of supramolecular complex composed of rigid dendritic porphyrin and fullerene, J. Am. Chem. Soc., 124, 5274-5275 (2002).
73. D. Sun, F. S. Tham, C. A. Reed, L. Chaker, M. Burgess and P. D.W. Boyd, Porphyrin-fullerene host-guest chemistry, J. Am. Chem. Soc., 122, 10704-10705 (2000).
74. D. Sun, F. S. Tham, C. A. Reed, L. Chaker and P. D. W. Boyd, Supramolecular fullereneporphyrin chemistry. fullerene complexation by metalated 'jaws porphyrin' hosts, J. Am. Chem. Soc., 124, 6604-6612 (2002).
75. Z.-Q.Wu, X.-B. Shao, C. Li, J.-L. Hou, K.Wang, X.-K. Jiang and Z.-T. Li, Hydrogen-bondingdriven preorganized zinc porphyrin receptors for efficient complexation of C60, C70, and C60 Derivatives, J. Am. Chem. Soc., 127, 17460-17468 (2005).
76. Y. Eda, K. Itoh,Y. N. Ito and T. Kawata, 2,6-Bis(porphyrin)-substituted pyrazine: a newclass of supramolecular synthon binding to a transition-metal ion and fullerene (C60), Tetrahedron, 65, 282-288 (2008).
77. T. Yamaguchi, N. Ishii, K. Tashiro and T. Aida, Supramolecular peapods composed of a metalloporphyrin nanotube and fullerenes, J. Am. Chem. Soc., 125, 13934-13935 (2003).
78. M. Ayabe, A. Ikeda, Y. Kubo, M. Takeuchi and S. Shinkai, A dendritic porphyrin receptor for C60 which features a profound positive allosteric effect, Angew. Chem. Int. Ed., 41, 2790-2792 (2002).
79. J.-Y. Zheng, K. Tashiro, Y. Hirabayashi, K. Kinbara, K. Saigo, T. Aida, S. Sakamoto and K. Yamaguchi, Cyclic dimers of metalloporphyrins as tunable hosts for fullerenes: a remarkable effect of rhodium(III), Angew. Chem. Int. Ed., 40, 1857-1861 (2001).
80. K. Tashiro and T. Aida, Metalloporphyrin hosts for supramolecular chemistry of fullerenes, Chem. Soc. Rev., 36, 189-197 (2007).
81. M. Yanagisawa, K. Tashiro, M. Yamasaki and T. Aida, 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 (2007).
82. Y. Shoji, K. Tashiro and T. Aida, Sensing of chiral fullerenes by a cyclic host with an asymmetrically distorted p-electronic component, J. Am. Chem. Soc., 128, 10690-10691 (2006).
83. H. Sato, K. Tashiro, H. Shinmori, A. Osuka, Y. Murata, K. Komatsu and T. Aida, Positive heterotropic cooperativity for selective guest binding via electronic communications through a fused zinc porphyrin array, J. Am. Chem. Soc., 127, 13086-13087 (2005).
84. A. L. Kieran, S. I. Pascu, T. Jarrosson and J. K. M. Sanders, Inclusion of C60 into an adjustable porphyrin dimmer generated by dynamic disulfide chemistry, Chem. Commun., 1276-1278 (2005).
85. H. Nobukuni, Y. Shimazaki, F. Tani and Y. Naruta, A nanotube of cyclic porphyrin dimers connected by nonclassical hydrogen bonds and its inclusion of C60 in a linear arrangement, Angew. Chem. Int. Ed., 46, 8975-8978 (2007).
86. Y.-B.Wang and Z. Lin, Supramolecular interactions between fullerenes and porphyrins, J. Am. Chem. Soc., 125, 6072-6073 (2003).
87. X. Peng, N. Komatsu, S. Bhattacharya, T. Shimawaki, S. Aonuma, T. Kimura and A. Osuka, Optically active single-walled carbon nanotubes, Nature Nanotechnology, 2, 361-365 (2007);
88. X. Peng, N. Komatsu, T. Kimura and A. Osuka, Improved optical enrichment of SWNTs through extraction with chiral nanotweezers of 2,6-pyridylene-bridged diporphyrins, J. Am. Chem. Soc., 129, 15947-15953 (2007).
89. H. Li, B. Zhou, L. Gu, W. Wang, K. A. S. Fernando, S. Kumar, L. F. Allard and Y.-P. Sun, Selective interactions of porphyrins with semiconducting single-walled carbon nanotubes, J. Am. Chem. Soc., 126, 1014-1015 (2004).
90. H. Becker, G. Javahery, S. Petrie, P. C. Cheng, H. Schwarz, L. T. Scott and D. K. Bohme, Gasphase ion/molecular reactions of corannulene, a fullerene subunit, J. Am. Chem. Soc., 115, 11636-11637 (1993).
91. P. E. Georghiou, A. H. Tran, S. Mizyed, M. Bancu and L. T. Scott, Concave polyarenes with sulfide-linked flaps and tentacles: new electron-rich hosts for fullerenes, J. Org. Chem., 70, 6158-6163 (2005).
92. Z.Wang, F. Dotz, V. Enkelmann and K.Mullen, 'Double-concave' graphene: permethoxylated hexa-peri-hexabenzocoronene and its cocrystals with hexafluorobenzene and fullerene, Angew. Chem. Int. Ed., 44, 1247-1250 (2005).
93. E. M. Perez, M. Sierra, L. Sanchez, M. Rosario, Torres, R.Viruela, P. M. Viruela, E. Orti and N. Martin, Concave tetrathiafulvalene-type donors as supramolecular partners for fullerenes, Angew. Chem. Int. Ed., 46, 1847-1851 (2007).
94. A. Sygula, F. R. Fronczek, R. Sygula, P.W. Rabideau and M. M. Olmstead, A double concave hydrocarbon buckycatcher, J. Am. Chem. Soc., 129, 3842-3843 (2007).
95. E. M. Perez, L. Sanchez, G. Fernadez and N. Martin, exTTF as a building block for fullerene receptors unexpected solvent-dependent positive homotropic cooperativity, J. Am. Chem. Soc., 128, 7172-7173 (2006).
96. E. M. Ferez, A. L. Capodilupo, G. Fernandez, L. Sanchez, P. M. Viruela, R. Viruela, E. Orti, M. Bietti and N. Martin, Weighting non-covalent forces in the molecular recognition of C60. Relevance of concave-convex complementarity, Chem. Commun., 4567-4569 (2008).
97. T. Kawase, H. R. Darabi and M. Oda, Cyclic [6]- and [8]Paraphenylacetylenes, Angew. Chem. Int. Ed. Engl., 35, 2662-2664 (1996).
98. T. Kawase and H. Kurata, Carbon nanorings and their complexing abilities: exploration of the concave-convex p-p Interaction, Chem. Rev., 106, 5250-5273 (2006).
99. T. Kawase, K. Tanaka, H. R. Darabi and M. Oda, Complexation of a carbon nanoring with fullerenes, Angew. Chem. Int. Ed., 42, 1624-1628 (2003).
100. T. Kawase and M. Oda, Complexation of carbon nanorings with fullerenes, Pure Appl. Chem., 78, 831-839 (2006).
101. T. Kawase, K.Tanaka,Y. Seirai, N. Shiono and M. Oda, Complexation of carbon nanorings with fullerenes. Novel supramolecular dynamics and structural tuning for a fullerene sensor, Angew. Chem. Int. Ed., 42, 5597-5600 (2003).
102. T. Kawase, N. Fujiwara, M. Tsutsumi, M. Oda, Y. Maeda, T. Wakahara and T. Akasaka, Supramolecular dynamics of cyclic [6]paraphenyleneacetylene complexes with [60]- and [70] fullerene derivatives: electronic and structural effect to the complexation, Angew. Chem. Int. Ed., 43, 5060-5062 (2004).
103. T. Kawase, K. Tanaka, N. Shiono, Y. Seirai and M. Oda, Onion-type complexation based on carbon nanorings and a buckminsterfullerene, Angew. Chem. Int. Ed., 43, 1722-1724 (2004).
104. T. Kawase, Y. Nishiyama, T. Nakamura, T. Ebi, K. Matsumoto, H. Kurata and M. Oda, Cyclic [5]Paraphenyleneacetylene: synthesis, properties and formation of a ring-in-ring complex showing considerably large association constant and entropy effect, Angew. Chem. Int. Ed., 46, 1086-1088 (2007).
105. D. Zhao and J. S. Moore, Shape-persistent aryl ethynylene macrocycles: syntheses and supramolecular chemistry, Chem. Commun., 807-818 (2003).