Abstract
The lowest excited singlet state of naphthoylnaphthvalene (NNV) undergoes valence isomerization yielding ground-state naphthoylnaphthalene (NN) finally. Neither the lowest excited singlet nor triplet state of NN is formed upon excitation of NNV, and of particular interest in photoinduced NNV→NNV valence isomerization is the existence of an intermediate which is probably either a bond-cloven species or a valence isomer of NNV. The lowest excited triplet state of NNV populated in benzene deactivates to its ground state, but that populated in ethanol abstracts a hydrogen atom from the solvent molecule generating the NNV ketyl radical. Interestingly, this radical also undergoes rapid valence isomerization and recombination of two NN ketyl radicals thus formed yields naphthopinacol. Synthesis of poly-tert-butylpolyacenes, tri-tert-butylisobenzofuran and tri-tert-butylpolyacenequinones, and furthermore, their photoinduced valence isomerization yielding the valene-type isomers as well as related photochromism and photo-electro dualchromism are presented.
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P.J. Darcy, H.G. Heller, P.J. Strydam and J. Whitall, J. Chem. Soc. Perkin Trans. 1, 202 (1981).
M. Irie and M. Mohri, J. Org. Chem. 53, 803 (1988).
M. Irie, O. Miyatake, K. Uchida and T. Eriguchi, J. Am. Chem. Soc. 116, 9894 (1994).
S. Miki, K. Matsuo, M. Yoshida and Z. Yoshida, Tetrahedron Lett. 29, 2211 (1988).
T. Nakayama, T. Yamaguchi, K. Ushida, K. Hamanoue, S. Miki, K. Matsuo and Z. Yoshida, Chem. Phys. Lett. 148, 259 (1988).
T. Nakayama, Y. Amijima, K. Ushida and K. Hamanoue, Chem. Phys. Lett. 258, 663 (1996).
S. Miki, H. Kagawa, K. Matsuo, O. Kobayashi, M. Yoshida and Z. Yoshida, Tetrahedron 48, 1567 (1992).
M.D. Newton, J.M. Schulman and M.M. Manus, J. Am. Chem. Soc. 96, 17 (1974).
T. Nakayama, T. Nagahara, S. Miki and K. Hamanoue, Chem. Phys. Lett. 266, 601 (1997).
T. Nakayama, T. Nagahara, S. Miki and K. Hamanoue, Chem. Lett. 597 (1997).
T. Nagahara, T. Nakayama, S. Miki and K. Hamanoue, J. Photochem. Photobiol. A:Chem. 124, 47 (1999).
N.J. Turro, P. Lechtken, A. Lyons, R.R. Hautala, E. Carnahan and T.J. Katz, J. Am. Chem. Soc. 95, 2035 (1973).
C.A. Renner, T.J. Katz, J. Pouliquen, N.J. Turro and W.H. Waddell, J. Am. Chem. Soc. 97, 2568 (1975).
K. Hamanoue, T. Nakayama, M. Shiozaki, Y. Funasaki, K. Nakajima and H. Teranishi, J. Chem. Phys. 85, 5698 (1986).
T. Nakayama, K. Hamanoue, Y. Funasaki and H. Teranishi, J. Chem. Phys. 87, 2677 (1987).
K. Hamanoue, T. Nakayama and M. Ito, J. Chem. Soc. Faraday Trans. 87, 3487 (1991).
K. Hamanoue and T. Nakayama, Res. Chem. Intermed. 22, 189 (1996).
T. Nakayama, T. Hamana, S. Miki and K. Hamanoue, J. Chem. Soc. Faraday Trans. 92, 1473 (1996).
K. Hamanoue, T. Nakayama, Y. Amijima and K. Ibuki, Chem. Phys. Lett. 267, 165 (1997).
T. Nakayama, Y. Torii, T. Nagahara and K. Hamanoue, J. Photochem. Photobiol. A:Chem. 119, 1 (1998).
T. Nakayama, Y. Torii, T. Nagahara, S. Miki and K. Hamanoue, J. Phys. Chem. 103, 1696 (1999).
N.J. Turro, C.A. Renner and T.J. Katz, Tetrahedron Lett. 4133 (1976).
T.J. Katz, E.J. Wang and N. Acton, J. Am. Chem. Soc. 93, 3782 (1971).
D. Bryce-Smith and H.C. Longuet-Higgins, J. Chem. Soc. Chem. Commun. 593 (1966).
D.P. Kjell and R.S. Sheridan, Tetrahedron Lett. 26, 5731 (1985).
L. Kaplan, J.S. Litscher and K.E. Wilzbach, J. Am. Chem. Soc. 88, 2881 (1966).
M.J.S. Dewar and S. Kirschner, J. Am. Chem. Soc. 97, 2932 (1975).
G. Ciamician and P. Silber, Ber. 33, 2911 (1911).
J.N. Pitts, R.L. Letsinger, R.P. Taylor, J.M. Patterson, G. Recktenwald and R.B. Martin, J. Am. Chem. Soc. 81, 1068 (1959).
C.S. Hammond and W.M. Moore, J. Am. Chem. Soc. 81, 6334 (1959).
R. Matsushima, T. Kishimoto and M. Suzuki, Chem. Lett. 579 (1976).
T. Shimizu, Y. Torii, S. Miki, T. Nakayama and K. Hamanoue, Abstracts of Symposium on Photochemistry 1996, Nagoya, Japan, p. 286.
R. Nakashima, K. Okamoto and T. Matsuura, Bull. Chem. Soc. Jpn. 49, 3355 (1976).
R. Matsushima, T. Kishimoto, M. Suzuki, M. Morioka and H. Mizuno, Bull. Chem. Soc. Jpn. 53, 2938 (1980).
T. Nakayama, T. Shimizu, Y. Torii, S. Miki and K. Hamanoue, J. Photochem. Photobiol. A:Chem. 111, 35 (1997).
C. Walling, in: P. de Mayo (Ed.), Molecular Rearrangements, Vol. 1, Interscience, New York, 1963, p. 440.
D.I. Davies and S. Cristol, Advan Free Radical Chem. 1, 155 (1965).
J.C. Martin, J.E. Schultz and J.W. Timberlake, Tetrahedron Lett. 4629 (1967).
M. Hanack and H.J. Schneider, Forschr. Chem. Forsch. 8, 554 (1967).
J.A. Landgrebe and L.W. Becker, J. Am. Chem. Soc. 90, 295 (1968).
J.K. Kochi, P.J. Krusic and D.R. Eaton, J. Am. Chem. Soc. 91, 1877 (1969).
N.C. Baird and M.J.S. Dewar, J. Am. Chem. Soc. 91, 352 (1969).
N.S. Isaacs, Physical Organic Chemistry, Longman, Harlow, 1987, p. 282.
Z. Yoshida, S. Miki, K. Matsuo and E. Shiojiri, Jpn Kokai Tokkyo Koho, JP 01238546 (1989)
S. Miki, T. Ema, R. Shimizu, H. Nakatsuji and Z. Yoshida, Tetrahedron Lett. 33, 1619 (1992).
S. Miki, M. Yoshida and Z. Yoshida, Bull. Chem. Soc. Jpn. 65, 932 (1992).
H.G. Viehe, Angew. Chem. Int. Ed. Engl. 4, 746 (1965).
E.E. van Tamelen, Acc. Chem. Res. 5, 186 (1972).
R. Sinrivasan, J. Am. Chem. Soc. 85, 4045 (1963).
W. Friedrichsen in R.P. Kreher (Ed.), Meth. Org. Chem. E6b, Georg Thieme Verlag, Stuttgart, 1994, p. 163.
S. Miki, J. Ito, R. Noda, N. Nishijima and K. Fukunishi, Tetrahedron 52, 4269 (1996).
S. Miki, R. Noda and K. Fukunishi, J. Chem. Soc. Chem. Commun. 925 (1997).
M. Zander, Ber. Bunsen. Physik. Chem. 71, 424 (1967).
G. Olbrich, O.E. Polansky and M. Zander, Ber. Bunsen. Physik. Chem. 81, 692 (1977).
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Nakayama, T., Miki, S. & Hamanoue, K. Photophysics and photochemistry of naphthoylnaphthvalene, and photoinduced valence isomerization of highly strained aromatic compounds (Or Quinones) yielding the valene-type isomers as well as related photochromism and photo-electro dualchromism. Res Chem Intermed 26, 327–346 (2000). https://doi.org/10.1163/156856700X00282
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DOI: https://doi.org/10.1163/156856700X00282