Abstract
Solid-state organic photochemistry is a promising field since solution photochemistry has been comprehensively developed over the last few decades. Crystals in which molecules are regularly arranged in three-dimensions have the possibility of more highly selective reactivity than in solution, as well as specific reactions that are different from those observed in solution. Hence, such crystals are attractive as a reaction medium.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
M. D. Cohen and G. M. Schmidt. J. Chem. Soc. (1964) 1996.
G. M. Schmidt. Pure Appl. Chem. 27 (1971) 647.
Organic solid State Chemistry“, edited by G. R. Desiraju. (Elsevier, Amsterdam, 1987).
Photochemistry in Solid Surfaces“, edited by M. Anpo and T. Matsuura. (Elsevier, Amsterdam, 1989).
Photochemistry in Organized and Constraint Media“, edited by v. Ramamurthy. (VCH, Weinheim, 1991).
Reactivity in Molecular Crystals“, edited by Y. Ohashi. (VCH, Kodansha, Tokyo,1993).
Supramolecular Photochemistry“, edited by v. Ramamurthy and K. Schanze. (Marcel Decker, New York, 1998).
F. Toda. Acc. Chem. Res. 28 (1995) 480.
J. N. Gamlin, R. Jones, M. Leibovitch, B. Patrick, J. R. Scheffer and J. Trotter. Acc. Chem. Res. 29 (1996) 203.
Y. Ito. Synthesis (1998) 1.
K. Tanaka and F. Toda. Chem. Rev. 100 (2000) 1025.
H. Koshima and T. Matsuura. Kokagaku 19 (1995) 10.
H. Koshima and T. Matsuura. J. Photochem. Photobiol. 100 (1996) 85.
A. I. Kitaigorodsky. “Molecular Crystals and Molecules”, ( Academic Press, New York, 1973 ).
G. R. Desiraju. “Crystal Engineering: The Design of Organic Solids”, ( Elsevier, Amsterdam, 1989 ).
G. A. Jeffrey. “An Introduction to Hydrogen Bonding”, (Oxford University Press, New York, 1997 ).
H. Koshima, D. P. Hessler Bittl, G. Miyoshi, Y. Wang and T. Matsuura. J. Photochem. Photobiol. A: Chem. 86 (1995) 171.
H. Koshima, Y. Chisaka, Y. Wang, X. Yao, H. Wang, R. Wang, A. Maeda and T. Matsuura. Tetrahedron 50 (1994) 13617.
J. B. Meng, W. G. Wang, H. G. Wang, T. Matsuura, H. Koshima, I. Sugimoto and Y. Ito. Photochem. Photobiol 57 (1993) 597.
H. Koshima, H. Ichimura and T. Matsuura. Chem. Lett. (1994) 847.
H. Koshima, H. Ichimura, K. Hirotsu, I. Miyahara, Y. Wang and T. Matsuura. J. Photochem. Photobiol. A: Chem. 85 (1995) 225.
H. Koshima and T. Matsuura. Mol. Cryst. Liq. Cryst. 277 (1996) 55.
H. Koshima, K. Ding, I. Miyahara, K. Hirotsu, M. Kanzaki and T. Matsuura. Photochem. Photobiol. A: Chem. 87 (1995) 219.
J. B. Meng, D. C. Fu, Z. H. Gao, R. J. Wang, H. G. Wang, I. Saito, R. Kasatani and T. Matsuura. Tetrahedron 46 (1990) 2367.
J. B. Meng, W. G. Wang, G. X. Xiong, Y. M. Wang, D. C. Fu, D. M. Du, R. J. Wang, H. G. Wang, H. Koshima and T. Matsuura. J. Photochem. Photobiol. A: Chem. 74 (1993) 43.
J. B. Meng, D. M. Du, G. X. Xiong, W. G. Wang, Y. M. Wang, H. Koshima and T. Matsuura. J. Heterocyclic Chem. 31 (1994) 121.
Y. Ito, J. B. Meng, S. Suzuki, Y. Kusunaga, T. Matsuura and K. Fukuyama. Tetrahedron Lett. 26 (1985) 2093.
J. B. Meng, Z. L. Zhu, R. J. Wang, X. K. Yao, Y. Ito, H. Ihara and T. Matsuura. Chem. Lett. (1990) 1247.
R. P. Wayne. “Photochemistry”, ( Butterworths, London, 1970 ) pp. 147–149.
Y. Ito, T. Matsuura and K. Fukuyama. Tetrahedron Lett. 29 (1988) 3087.
H. Koshima, X. Yao, H. Wang, R. Wang and T. Matsuura. Tetrahedron Lett. 35 (1994) 4801.
M. Lahav, L. Lerserowitz, R. Popovits-Biro and C.-P. Tang. J. Am. Chem. SOC. 100 (1978) 2542.
C. P. Tang, H. C. Chang, R. Popovitz-Biro, F. Frolow, M. Lahav, L. Lerserowitz and R. K. Mcmullan. J. Am. Chem. Soc. 107 (1985) 4058.
H. C. Chang, R. Popovitz-Biro, M. Lahav and L. Lerserowitz. J. Am. Chem. SOC. 109 (1987) 3883.
Y. Weisinger-Lewin, M. Vaida, R. Popovitz-Biro, H. C. Chang, F. Mannig, F. Frolow, M. Lahav and L. Leiserowitz. Tetrahedron 43 (1987) 1449.
H. Koshima, Y. Wang, T. Matsuura, I. Miyahara, H. Mizutani, K. Hirotsu, T. Asahi and H. Masuhara. J. Chem. Soc. Perkin Trans. 2 (1997) 2033.
T. Asahi, Y. Matsuo and H. Masuhara. Chem. Phys. Lett. 256 (1996) 525.
Y. Ito, S. Endo and S. Ohba. J. Am. Chem. Soc. 119 (1997) 5974.
J. B. Meng, W. G. Wang, Y. M. Wang, H. G. Wang, H. Koshima and T. Matsuura. Mol. Cryst. Liq. Cryst. 242 (1994) 135
A. Matsumoto, T. Odani, M. Chikada, K. Sada and M. Miyata. J Am. Chem. Soc. 121 (1999) 11122.
A. Matsumoto, S. Nagahama and T. Odani. J. Am. Chem. Soc 122 (2000) 9109.
A. Matsumoto, T. Odani, K. Sada, M. Miyata and K. Tashiro. Nature 405 (2000) 328.
M. Hasegawa, Y. Suzuki, F. Suzuki and H. Nakanishi. J. Polym. Sci. Part A-I 7 (1969) 743.
M. Hasagawa, M. Aoyama, Y. Maekawa and Y. Ohashi. Macromolecules 22 (1989) 1568.
M. Hasegawa, K. Kinbara, Y. Adegawa and K. Saigo. J. Am. Chem. Soc. 115 (1993) 3820.
J. A. R. P. Sarma and G. R. Desiraju. J. Chem. Soc., Chem. Commun. (1984) 145.
J. A. R. P. Sarma and G. R. Desiraju. J. Am. Chem. Soc. 108 (1986) 2791.
J. A. R. P. Sarma and G. R. Desiraju. J. Chem. Soc., Perkin Trans. 2 (1987) 1187.
N. Haga, H. Nakajima, H. Takayanagi and K. Tokumaru. J. Chem. Soc., Chem. Commun. (1997) 1171.
N. Haga, H. Nakajima, H. Takayanagi and K. Tokumaru. J. Org. Chem. 63 (1998) 5372.
Y. Tto, T. Matsuura and K. Fukuyama. Tetrahedron Lett. 29 (1988) 2087.
B. Bosch, S. M. Hubig, S. V. Lindeman and J. K. Kochi. J. Org. Chem. 63 (1998) 592.
N. Hayahi, Y. Mazaki and K. Kobayashi. Tetrahedron Lett. 35 (1994) 5883.
Y. Mazaki, N. Hayashi and K. Kobayashi. J. Chem. Soc., Chem. Commun. (1992) 1381.
Y. Mazaki, K. Awaga and K. Kobayashi. J. Chem. Soc., Chem. Commun. (1992) 1661.
N. Hayashi, Y. Mazaki and K. Koyabashi. Chem. Lett. (1992) 1689.
Photoinduced Electron Transfer, part C“, edited by M. A. Fox and M. Chanon. ( Elsevier, Amsterdam, 1988 ).
C. Budac and P. Wan. J. Photochem. Photobiol. A: Chem. 67 (1994) 135.
R. Noyori, M. Kato, M. Kawanishi and H. Nozaki. Tetrahedron 25 (1969) 1125.
D. R. G. Brimage, R. S. Davidson and P. R. Steiner. J. Chem. Soc., Perkin Trans. 1 (1973) 526.
K. Okada, K. Okubo and M. Oda. Tetrahedron Lett. 30 (1989) 6733.
K. Okada, K. Okubo and M. Oda. J. Photochem. Photobiol. A: Chem. 57 (1991) 265.
K. Tsujimoto, N. Nakao and M. Ohashi. J. Chem. Soc., Chem. Commun. (1992) 366.
J. Libman. J. Am. Chem. Soc. 97 (1975) 4139.
H. Koshima, K. Ding and T. Matsuura. J. Chem. Soc., Chem. Commun. (1994) 2053.
H. Koshima, K. Ding, Y. Chisaka, T. Matsuura, I. Miyahara and K. Hirotsu. J. Am. Chem. Soc. 119 (1997) 10317.
H. Koshima, K. Ding, Y. Chisaka, T. Matsuura, Y. Ohashi and M. Mukasa. J. Org. Chem. 61 (1996) 2352.
H. Koshima, K. Ding, Y. Chisaka and T. Matsuura. Tetrahedron: Asymmetry 6 (1995) 101.
H. Koshima, T. Nakagawa and T. M. Matsuura. Tetrahedron Lett. 38 (1997) 6063.
H. Koshima, E. Hayashi, K. Shirafuji, M. Hamada, D. Matsushige, M. Miyauchi and T. Matsuura. J. Photochem. Photobiol., A: Chem. 129 (1999) 121.
H. Koshima, K. Ding, T. Miura and T. Matsuura. J Photochem. Photobiol., A: Chem. 104 (1997) 105.
H. Koshima, D. Matsushige, M. Miyauchi and J. Fujita. Tetrahedron 56 (2000) 6845.
H. Koshima, K. Ding, Y. Chisaka and T. Matsuura. J Am. Chem. Soc. 118 (1996) 12059.
J. Jacques, A. Collet and S. H. Wilen. “Enantiomers, Racemates, and Resolutions”, ( Wiley-Interscience, New York, 1981 ).
H. Koshima and T. Matsuura. J. Synth. Org. Chem. 56 (1998) 268.
H. Koshima and T. Matsuura. J. Synth. Org. Chem. 56 (1998) 466.
L. Addadi and M. Lahav. “Origin of Optical Activity in Nature”, edited by D. C. Walker. (Elsevier, New York, 1979) Chap. 14.
B. S. Green, M. Lahav and D. Ravinovich. ACC. Chem. Res. 69 (1979) 191.
M. Hasegawa. Chem. Rev. 83 (1983) 507.
M. Sakamoto. Chem. Eur. J. 3 (1997) 684.
B. L. Feringa and R. A. Delden. Angew. Chem. Int. Ed. 39 (1999) 3418.
F. H. Herbstein and M. Kaftory. Acta Crystallogr. B31 (1975) 60.
A. Thozet and J. Gaultier. Acta Crystallogr. B31 (1977) 1051.
B. Shaanan and U. Shmuell Acta Crystallogr. B36 (1980) 2076.
H. Koshima, E. Hayashi, T. Matsuura, K. Tanaka and F. Toda. Tetrahedron Lett. 38 (1997) 15009.
H. Koshima, E. Hayashi and T. Matsuura. Supramol. Chem. 11 (1999) 57.
H. Koshima, S. I. Khan and M. A. Garcia-Garibay. Tetrahedron: Asymmetry 9 (1998) 1851.
H. Koshima and S. Honke. J. Org. Chem. 64 (1999) 790.
H. Koshima, S. Honke and J. Fujtta. J. Org. Chem. 64 (1999) 3916.
H. Koshima, S. Honke and M. Miyauchi. Enantiomer 5 (2000) 125.
H. Koshima, M. Miyauchi and M. Shiro. Supramol. Chem. 13 (2001) 137.
S. V. Evans, M. A. Garcia-Garibay, N. Omkaram, J. R. Scheffer, J. Trotter and F. Wireko. J. Am. Chem. Soc. 108 (1986) 5648.
M. A. Garcia-Garibay, J. R. Scheffer, J. Trotter and F. Wireko. J. Am. Chem. Soc. 111 (1989) 4985.
J. Chen, P. R. Pokkuluri, J. R. Scheffer and J. Trotter. Tetrahedron Lett. 31 (1990) 6803.
T. Y. Fu, Z. Liu, J. R. Scheffer and J. Trotter. J. Am. Chem. Soc. 115 (1993) 12202.
A. L. Roughton, M. Muneer and M. Demuth. J. Am. Chem. Soc. 115 (1993) 2085.
F. Toda, M. Vagi and S. Soda. J. Chem. Soc., Chem. Commun. (1987) 1413.
A. Sekine, K. Hori, Y. Ohashi, M. Yagi and F. Toda. J. Am. Chem. Soc. 111 (1989) 697.
F. Toda and H. Miyamoto. J. Chem. Soc., Perkin Trans. 1 (1993) 1129.
D. Hashizume, H. Kogo, A. Sekine, Y. Ohashi, H. Miyamoto and F. Toda. J. Chem. Soc. Perkin Trans. 2 (1996) 61.
D. Hashizume, H. Kogo, A. Sekine, Y. Ohashi, H. Miyamoto and F. Toda. Acta Crystallogr. C51 (1995) 929.
F. Toda and K. Tanaka. Supramol. Chem. 3 (1994) 87.
F. Ioda, K. Tanaka, Z. Stein and I. Goldberg. Acta Crystallogr B51 (1995) 856.
F. Toda, K. Tanaka, Z. Stein and I. Goldberg. Acta Crystallogr. C51 (1995) 2722.
M. Sakamoto, M. Takahashi, T. Fujita, S. Watanabe, I. Iida, T. Nishio and H. AOYAMA. J. Org. Chem. 58 (1993) 3476.
M. Sakamoto, N. Hokari, M. Takahashi, T. Fujita, S. Watanabe, I. Iida and T. Nishio. J. Am. Chem. Soc. 115 (1993) 818.
M. Sakamoto, M. Takahashi, T. Shimizu, T. Fujita, S. Nishio, I. Ikuo, K. Yamaguchi and S. Watanabe. J. Org. Chem. 60 (1995) 7088.
M. Sakamoto, M. Takahashi, K. Kamiya, K. Yamaguchi, T. Fujita and S. Watanabe. J. Am. Chem. Soc. 118 (1996) 10664.
M. Sakamoto, M. Takahashi, S. Moriizumi, K. Yamaguchi, T. Fujita and S. Watanabe. J. Am. Chem. Soc. 118 (1996) 8138.
M. Sakamoto, M. Takahashi, N. Sekine, T. Fujita, S. Watanabe and K. Yamaguchi. J. Am. Chem. Soc. 120 (1998) 12770.
L. Addadi, J. Mil and M. Lahav. J. Am. Chem. Soc. 104 (1982) 3422.
C.-M. Chung and M. Hasegawa. J. Am. Chem. Soc. 113 (1991) 7311.
A. Elgavi, B. S. Green and G. M. J. Schmidt. J. Am. Chem. Soc. 95 (1973) 2058.
T. Suzuki, T. Fukushima, Y. Yamashita and T. Miyashi. J. Am. Chem. Soc. 116 (1994) 2793.
T. Suzuki, H. Fujii, Y. Yamashita, C. Kabuto, S. Tanaka, M. Harasawa, T. Mukai and T. Miyashi. J. Am. Chem. Soc. 114 (1992) 3034.
H. Koshima, T. Nakagawa, T. Matsuura, H. Miyamoto and F. Toda. J. Org. Chem. 62 (1997) 6322.
E. B. Fleischer, N. Sung and S. Hawkinson. J. Phys. Chem. 72 (1968) 4311.
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2002 Springer Science+Business Media Dordrecht
About this chapter
Cite this chapter
Koshima, H. (2002). Solid-State Bimolecular Photoreactions in Two-Component Molecular Crystals. In: Toda, F. (eds) Organic Solid-State Reactions. Springer, Dordrecht. https://doi.org/10.1007/978-94-017-0089-4_6
Download citation
DOI: https://doi.org/10.1007/978-94-017-0089-4_6
Publisher Name: Springer, Dordrecht
Print ISBN: 978-90-481-5923-9
Online ISBN: 978-94-017-0089-4
eBook Packages: Springer Book Archive