Solid state photochemistry for fullerene functionalization: Solid state photoinduced electron transfer in the diels-alder reaction with anthracenes

Tetrahedron Letters

Volumn 39, Issue 22, 1998, Pages 3733-3736

  Mikami, Koichi ^a   Matsumoto, Shoji ^a   Tonoi, Takayuki ^a   Okubo, Yasutaka ^a   Suenobu, Tomoyoshi ^b   Fukuzumi, Shunichi ^b  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTHRACENE DERIVATIVE; FULLERENE; FUNCTIONAL GROUP; SOLVENT;

ARTICLE; CHEMICAL REACTION; ELECTRON TRANSPORT; ENERGY TRANSFER; IONIZATION; PHOTOACTIVATION; PHOTOCHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID STATE; STEREOCHEMISTRY;

BETULACEAE;

EID: 0032575192     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00572-3     Document Type: Article

References (28)

1. 1 This work has been presented at the 12th Fullerene General Symposium, Tokyo, January 13-14, 1997: Abstr. No. 8 and the Annual Meeting of the Chemical Society of Japan, Tokyo, March 27-30, 1997: Abstr. No. 3H307.
2. 2 (a) Comprehensive reviews of fullerene: Hirsch, A. The Chemistry of the Fullerenes; Thieme: Stuttgart, 1994.
3. (b) Krätschmer, W.; Lamb, L. D.; Fostiropoulous, K.; Huffman, D. R. Nature 1990, 347, 354.
4. (c) Haufler, R. E.; Conceicao, J.; Chibante, L. P. F.; Chai, Y.; Byrne, N. E.; Flanagan, S.; Haley, M. M.; O'Brien, S. C.; Pan, C.; Xiao, Z.; Billups, W. E.; Ciufolini, M. A.; Hauge, R. H.; Margrave, J. L.; Wilson, L. J.; Curl, R. F.; Smalley, R. E. J. Phys. Chem. 1990, 94, 8634.
5. (d) Kroto, H. W.; Heath, J. R.; O'Brien, S. C.; Curl, R. F.; Smalley, R. E. Nature 1985, 318, 162.
6. (e) Also see: Osawa, E. Kagaku (Chemistry) 1970, 25, 854. Chem. Abst. 1971, 74(8): 75698v.
7. (e) Also see: Osawa, E. Kagaku (Chemistry) 1970, 25, 854. Chem. Abst. 1971, 74(8): 75698v.
8. 3 Ruoff, R. S.; Tse, D. S.; Malhotra, R.; Lorents, D. C. J. Phys. Chem. 1993, 97, 3379.
9. 4 Reviews on reactions in solid state: (a) Reactivity in Molecular Crystals, Ohashi, Y. Ed.; VCH-Kodansha: Tokyo, 1993.
10. (b) Photochemistry in Organized and Constrained Media, Ramamurthy, V. Ed.; VCH: New York, 1991.
11. (c) Toda, F, Top. Curr. Chem. 1988, 149, 211. Toda, F. Acc. Chem. Res. 1995, 28, 480. Quite recently, solid-state reactions of fullerene have been reported, however, without photochemical irradiation:
12. (c) Toda, F, Top. Curr. Chem. 1988, 149, 211. Toda, F. Acc. Chem. Res. 1995, 28, 480. Quite recently, solid-state reactions of fullerene have been reported, however, without photochemical irradiation:
13. 60 by mechanical force: Wang, G. -W.; Komatsu, K.; Murata, Y.; Shiro, M. Nature 1997, 387, 583.
14. 60 in solid state by mechanical force: Wang, G. -W.; Murata, Y.; Komatsu, K.; Wan, T. S. M. Chem. Commun. 1996, 2059.
15. 60 and anthracene adduct under thermal conditions: Kräutler, B.; Müller, T.; Maynollo, J.; Gruber, K.; Kratky, C.; Ochsenbein, P.; Schwarzenbach, D.; Bürgi, H. -B. Angew. Chem., Int. Ed. Engl. 1996, 35, 1204.
16. 5 Ohno, M.; Koide, N.; Sato, H.; Eguchi, S. Tetrahedron 1997, 53, 9075, and references cited therein.
17. 60 and anthracene in solution: (a) Lamparth, I.; Maichle-Mössmer, C.; Hirsh, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 1607.
18. (b) Komatsu, K.; Murata, Y.; Sugita, N.; Takeuchi, K.; Wan, T. S. M. Tetrahedron Lett. 1993, 34, 8473.
19. (c) Tsuda, M.; Ishida, T.; Nogami, T.; Kurono, S.; Ohashi, M. J. Chem. Soc., Chem. Commun. 1993, 1296.
20. (d) Schlueter, J. A.; Seaman, J. M.; Taha, S.; Cohen, H.; Lykke, K. R.; Wang, H. H.; Williams, J. M. J. Chem. Soc., Chem. Commun. 1993, 972.
21. f = 0.09 (hexane/toluene = 5 : 1).
22. 8 Fukuzumi, S.; Kochi, J. K. Tetrahedron 1982, 38, 1035.
23. 60 (2.7 eV) and the excitation energy of the triplet state (1.57 eV); see: Yang, S. H.; Pettiette, Conceicao, J.; Cheshnovsky, O.; Smalley, R. E. Chem. Phys. Lett. 1987, 139, 233. Zeng, Y.; Biczok, L.; Linschitz, H. J. Phys. Chem. 1992, 96, 5237.
24. 60 (2.7 eV) and the excitation energy of the triplet state (1.57 eV); see: Yang, S. H.; Pettiette, Conceicao, J.; Cheshnovsky, O.; Smalley, R. E. Chem. Phys. Lett. 1987, 139, 233. Zeng, Y.; Biczok, L.; Linschitz, H. J. Phys. Chem. 1992, 96, 5237.
25. 60 complex in PhCN was determined as 2.55 eV, from which the Coulomb interaction energy in PhCN was derived as 2.08 eV (7.33 - 2.7 - 2.55). The Coulombic interaction in the solid state is expected to be larger than 2.08 eV.
26. 11 A similar reaction in solution: (a) Mikami, K.; Matsumoto, S. Synlett 1995, 229.
27. (b) Mikami, K.; Matsumoto, S.; Ishida, A.; Takamuku, S.; Suenobu, T.; Fukuzumi, S. J. Am. Chem. Soc. 1995, 117, 11134.
28. (c) Tokuyama, H.; Isobe, H.; Nakamura, E. J. Chem. Soc., Chem. Commun. 1994, 2753.