Host-guest complexation of endohedral metallofullerene with azacrown ether and its application

Journal of the American Chemical Society

Volumn 128, Issue 20, 2006, Pages 6699-6703

  Tsuchiya, Takahiro ^a   Sato, Kumiko ^a   Kurihara, Hiroki ^a   Wakahara, Takatsugu ^a   Nakahodo, Tsukasa ^a   Maeda, Yutaka ^b   Akasaka, Takeshi ^a   Ohkubo, Kei ^c   Fukuzumi, Shunich ^c   Kato, Tatsuhisa ^d   Mizorogi, Naomi ^e   Kobayashi, Kaoru ^e   Nagase, Shigeru ^e  

^a UNIVERSITY OF TSUKUBA   (Japan)

^b TOKYO GAKUGEI UNIVERSITY   (Japan)

^c OSAKA UNIVERSITY   (Japan)

^d JOSAI UNIVERSITY   (Japan)

^e INSTITUTE FOR MOLECULAR SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTRON TRANSITIONS; FULLERENES; LANTHANUM; METAL ANALYSIS;

AZACROWN ETHERS; ENDOHEDRAL METALLOFULLERENES; MACROCYCLIC COMPOUNDS; METALLOFULLERENES;

ETHERS;

1,4,7,10,13,16 HEXAAZACYCLOOCTADECANE; 1,4,7,10,13,16 HEXAMETHYL 1,4,7,10,13,16 HEXAAZACYCLOOCTADECANE; 18 CROWN 6 ETHER; 4 TERT BUTYLCALIX[N]ARENE DERIVATIVE; CALIXARENE; CROWN ETHER DERIVATIVE; DECANE; FULLERENE DERIVATIVE; LANTHANUM; METALLOFULLERENE; MONOAZA 18 CROWN 6 ETHER; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; COMPLEX FORMATION; ELECTRON TRANSPORT; OXIDATION REDUCTION POTENTIAL; REDUCTION KINETICS; SOOT; TRANSPORT KINETICS;

EID: 33646733432     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0608390     Document Type: Article

References (48)

1. Fullerenes: Chemistry, Physics, and Technology; Kadish, K. M., Ruoff, R. S., Eds.; Wiley: New York, 2000.
2. (a) Atwood, J. L.; Koutsantonis, G. A.; Raston, C. L. Nature 1994, 368, 229-231.
3. (b) Suzuki, T.; Nakashima, K.; Shinkai, S. Chem. Lett. 1994, 699-702.
4. Haino, T.; Yamanaka, Y.; Araki, H.; Fukazawa, Y. Chem. Commun. 2002, 402-403.
5. Dinnebier, R. E.; Gunnarsson, O.; Brumm, H.; Koch, E.; Stephens, P. W.; Huq, A.; Jansen, M. Science 2002, 269, 109-113.
6. (a) Bhattacharya, S.; Sharma, A.; Nayak, S. K.; Chattopadhyay, S.; Mukherjee, A. K. J. Phys. Chem. B 2003, 107, 4213-4217.
7. (b) van Eis, M. J.; Seiler, P.; Muslinkina, L. A.; Badertscher, M.; Pretsch, E.; Diederich, F.; Alvarado, R. J.; Echegoyen, L.; Nunez, I. P. Helv. Chim. Acta 2002, 85, 2009-2055.
8. (a) Bhattacharya, S.; Nayak, S. K.; Chattopadhyay, S.; Banerjee, M.; Mukherjee, A. K. J. Phys. Chem. B 2003, 107, 11830-11834.
9. (b) Poor, B.; Biczok, L.; Kubinyi, M. Phys. Chem. Chem. Phys. 2003, 5, 2047-2052.
10. (c) Ikeda, A.; Suzuki, Y.; Yoshimura, M.; Shinkai, S. Tetrahedron 1998, 54, 2497-2508.
11. (d) Haino, T.; Yanase, M.; Fukazawa, Y. Angew. Chem., Int. Ed. Engl. 1997, 36, 259-260.
12. (e) Araki, K.; Akao, K.; Ikeda, A.; Suzuki, T.; Shinkai, S. Tetrahedron Lett. 1996, 37, 73-76.
13. (a) Murthy, C. N.; Geckeler, K. E. Chem. Commun. 2001, 1194-1195.
14. (b) Komatsu, K.; Fujiwara, K.; Murata, Y.; Braun, T. J. Chem. Soc., Perkin Trans, 1 1999, 2963-2966.
15. (c) Yoshida, Z. I.; Takekuma, H.; Takekuma, S. I.; Matsubara, Y. Angew. Chem., Int. Ed. Engl. 1994, 33, 1597-1599.
16. (a) Shoji, Y.; Tashiro, K.; Aida, T. J. Am. Chem. Soc. 2004, 126, 6570-6571.
17. (b) Kubo, Y.; Susasaki, A.; Ikeda, M.; Sugiyasu, K.; Sonoda, K.; Ikeda, A.; Takeuchi, M.; Shinkai, S. Org. Lett. 2002, 4, 925-928.
18. (c) Tashiro, K.; Aida, T.; Zheng, J. Y.; Kinbara, K.; Saigo, K.; Sakamoto, S.; Yamaguchi, K. J. Am. Chem. Soc. 1999, 121, 9477-9478.
19. (a) Kobayashi, K.; Nagase, S. In Endofullerenes: A New Family of Carbon Clusters: Akasaka, T., Nagase, S., Eds.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 2002; pp 99-119.
20. (b) Wakahara, T.; Akasaka, T.; Kobayashi, K.; Nagase, S. In Endofullerenes: A New Familv of Carbon Clustery, Akasaka, T., Nagase, S., Eds.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 2002; pp 231-251.
21. (c) Nagase, S.; Kobayashi, K.; Akasaka, T.; Wakahara, T. In Fullerenes: Chemistry, Physics and Technology, Kadish, K., Ruoff, R. S., Eds.; John Wiley & Sons: New York, 2000: pp 231-251.
22. (d) Shinohara, H. Rep. Prog. Phys. 2000, 63, 843-892.
23. (e) Nagase, S.; Kobayashi, K.; Akasaka, T. J. Comput. Chem. 1998, 19, 232-239.
24. (f) Nagase, S.; Kobayashi, K.; Akasaka, T. Bull. Chem. Soc. Jpn. 1996, 69, 2131-2142.
25. (g) Bethune, D. S.; Johnson, R. D.; Salem, J. R.; de Vries, M. S.; Yannoni, C. S. Nature 1993, 366, 123-128.
26. Kubozono, Y.; Hiraoka, K.; Takabayashi, Y.; Nakai, T.; Ohta, T.; Maeda, H.; Ishida, H. Chem. Lett. 1996, 1061-1062.
27. Lian, Y. F.; Yang, S. F.; Yang, S. H. J. Phys. Chem. B 2002, 106, 3112-3117.
28. Lian, Y. F.; Shi, Z.; Zhou, X.; Gu, Z. Chem. Mater. 2004, 16, 1704-1714.
29. Akasaka, T.; et al. J. Am. Chem. Soc. 2000, 122, 9316-9317.
30. (a) Schick, G.; Kampe, K.-D.; Hirsch, A. Chem. Commun. 1995, 2023-2024.
31. (b) Lawson, G. E.; Kitaygorodskiy, A.; Ma, B.; Bunker, C. E.; Sun, Y.-P. Chem. Commun. 1995, 2225-2226.
32. Aragó, J.; Bencini, A.; Bianchi, A.; Garcia-España, E.; Micheloni, M.; Paoletti, P.; Ramirez, J. A.; Paoli, P. Inorg. Chem. 1991, 30, 1843.
33. The details about the complexation of 1 with TMPD will be published separately.
34. (a) Matsubara, H.; Oguri, S.; Asano, K.; Yamamoto, K. Chem. Lett. 1999, 431-432.
35. (b) Seshadri, R.; D'souza, F.; Krishnan, V.; Rao, C. N. R. Chem. Lett. 1993, 217-220.
36. Baungarten, M.; Gügel, A.; Gherghel, L. Adv. Mater. 1993, 5, 458-461.
37. (a) Konishi, T.; Ikeda, A.; Kishida, T.; Rasmussen, B. S.; Fujitsuka, M.; Ito, O.; Shinkai, S. J. Phys. Chem. A 2002, 106, 10254-10260.
38. (b) Schilder, A.; Gotschy, B.; Seidl, A.; Gompper, R. Chem. Phys. 1995, 193, 321-326.
39. (C) Klos, H.; Rystau, I.; Schütz, W.; Gotschy, B.; Skiebe, A.; Hirsh, A. Chem. Phys. Lett. 1994, 224, 333-337.
40. Isobe, H.; Tanaka, T.; Nakanishi, W.; Lemiègre, L.; Nakamura, E. J. Org. Chem. 2005, 70, 4826-4832.
41. (a) Ofial, A. R.; Ohkubo, K.; Fukuzumi, S.; Lucius, R.; Mayr, H. J. Am. Chem. Soc. 2003, 125, 10906-10912.
42. (b) Fukuzumi, S.; Ohkubo, K.; Imahori, H.; Guldi, D. M. Chem.-Eur. J. 2003, 9, 1585-1593.
43. 2aε) in nitrobenzene, the value of -0.03 eV was employed.
44. Tsuchiya, T.; Wakahara, T.; Shirakura, S.; Maeda, Y.; Akasaka, T.; Kobayashi, K.; Nagase, S.; Kato, T.; Kadish, K. M. Chem. Mater. 2004, 16, 4343-4346.
45. (a) Suzuki, T.; Maruyama, Y.; Kato, T.; Kikuchi, K.; Nakao, Y.; Achiba, Y.; Kobayashi, K.; Nagase, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 1094-1096.
46. (b) Yamamoto, K.; Funasaka, H.; Takahashi, T.; Akasaka, T. J. Phys. Chem. 1994, 98, 2008-2011.
47. (c) Yamamoto, K.; Funasaka, H.; Takahashi, T.; Akasaka, T.; Suzuki, T.; Maruyama, Y. J. Phys. Chem. 1994, 98, 12831-12833.
48. Rehm, D.; Weller, A. Isr. J. Chem. 1970, 8, 259.