Photoinduced hydrogen atom transfer in trans-1-(1′-hydroxy-2′- naphthyl)-3-(1-naphthyl)-2-propen-1-one

Photochemical and Photobiological Sciences

Volumn 2, Issue 4, 2003, Pages 402-406

  Kaneda, Kaoru ^a   Arai, Tatsuo ^a  

^a UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1 (1' HYDROXY 2' NAPHTHYL) 3 (1 NAPHTHYL) 2 PROPEN 1 ONE; BENZENE; NAPHTHYL GROUP; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; FLUORESCENCE; LIGHT; PHOTOCHEMISTRY; PHOTOLYSIS; PRIORITY JOURNAL; PROTON TRANSPORT; ROOM TEMPERATURE;

EID: 0142006381     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/b211834n     Document Type: Article

References (29)

1. G. Montaudo and S. Caccamese, Structure and conformation of chalcone photodimers and related compounds, J. Org. Chem., 1973, 38, 710.
2. F. Pina, M. J. Melo, M. Maestri, P. Passaniti, N. Camaioni and V. Balzani, Photo- and pH-induced transformations of flavylium cation: "Write-lock-read-unlock-erase" cycles, Eur. J. Org. Chem., 1999, 3199.
3. A. Roque, C. Lodeiro, F. Pina, M. Maestri, R. Ballardini and V. Balzani, Photochromic properties of 3-methyl-substituted flavylium salts, Eur. J. Org. Chem., 2002, 2699.
4. D. E. Nicodem, J. A. de and M. G. Matos, Photoisomerization of chalcone: Wavelength dependence, J. Photochem., 1981, 15, 193.
5. R. Matsushima, K. Kato and S. Ishigai, Photochromism of 2-hydroxychalcones in solid hydrogel matrices, Bull. Chem. Soc. Jpn., 2002, 75, 2079.
6. H. Horiuchi, A. Yokawa, T. Okutsu and H. Hiratsuka, Laser flash photolysis studies of the photo-ring-opening reaction of flav-3-en-2-ol, Bull. Chem. Soc. Jpn., 1999, 72, 2429.
7. H. Horiuchi, H. Shirase, T. Okutsu, R. Matsushima and H. Hiratsuka, Photochromism of 2-hydroxy-4′-methoxychalcone: A novel photon-mode erasable optical memory system with nondestructive readout ability, Chem. Lett., 2000, 96.
8. R. Matsushima and T. Murakami, Photoreactions of 3-(2-hydroxyphenyl)-1- (substituted phenyl)-2-propen-1-ones (substituted 2-hydroxychalcones) in organic solvents in the presence and absence of acid, Bull. Chem. Soc. Jpn., 2000, 73, 2215.
9. F. Ito, N. Tanaka, A. Katsuki and T. Fujii, Why do flavylium salts show so various colors in solution? Effect of concentration and water on the flavylium's color changes, J. Photochem. Photobiol., A, 2002, 150, 153.
10. R. Matsushima and I. Hirao, Photocyclization of 2′-hydroxychalcones to 4-flavanones, Bull. Chem. Soc. Jpn., 1980, 53, 518.
11. R. Matsushima and H. Kageyama, Photochemical cyclization of 2′-hydroxychalcones, J. Chem. Soc., Perkin Trans. 2, 1985, 6, 743.
12. P. T. Chou, M. L. Martinez and W. C. Cooper, Direct evidence of excited-state intramolecular proton transfer in 2′-hydroxychalcone and photooxygenation forming 3-hydroxyflavone, J. Am. Chem. Soc., 1992, 114, 4943.
13. K. Tokumura, K. Nagaosa, Y. Ohta and R. Matsushima, Temperature-dependent tautomer fluorescence spectra of 3′,4′-benzo-2′- hydroxychalcone: Direct evidence for photoenolization followed by Z → E isomerization in the sinelet manifold, Chem. Phys. Lett., 1998, 295, 516.
14. T. Arai and Y. Norikane, Direct observation of the photoinduced hydrogen atom transfer in 2′-hydroxychalcone, Chem. Lett., 1997, 339.
15. Y. Norikane, H. Itoh and T. Arai, Control of the photoisomerization mode of carbon-carbon double bond by intramolecular hydrogen bond; One-way photoisomerization of 2′-hydroxychalcone induced by adiabatic intramolecular hydrogen atom transfer, Chem. Lett., 2000, 1094.
16. Y. Norikane, H. Itoh and T. Arai, Photochemistry of 2′- hydroxychalcone. One-way cis-trans photoisomerization induced by adiabatic intramolecular hydrogen atom transfer, J. Phys. Chem. A, 2002, 106, 2766.
17. R. A. Caldwell and M. Singh, Effect of a polar substituent on olefin triplet lifetime, J. Am. Chem. Soc., 1983, 105, 5139.
18. A. Weller, Intramolecular proton transfer in excited states, Z. Elektrochem., 1956, 60, 1144.
19. T. Arai, M. Moriyama and K. Tokumaru, Novel photoinduced hydrogen atom transfer through intramolecular hydrogen bonding coupled with cis-trans isomerization in cis-1-(2-pyrrolyl)-2-(2-quinolyl)ethene, J. Am. Chem. Soc., 1994, 116, 3171.
20. P. F. Barbara and P. K. Walsh, Picosecond kinetic and vibrationally resolved spectroscopic studies of intramolecular excited-state hydrogen atom transfer, J. Phys. Chem., 1989, 93, 29.
21. S. J. Formosinho and L. G. Arnaut, Excited-state proton transfer reactions II. Intramolecular reactions, J. Photochem. Photobiol., A, 1993, 75, 21.
22. J. Catalán, J. Palomar and J. L. G. de Paz, Intramolecular proton or hydrogen-atom transfer in the ground and excited states of 2-hydroxybenzoyl compounds, J. Phys. Chem. A, 1997, 101, 7914.
23. S. Maheshwari, A. Chowdhury, N. Sathyamurthy, H. Mishra, H. B. Tripathi, M. Panda and J. Chandrasekhar, Ground and excited state intramolecular proton transfer in salicylic acid: An ab initio electronic structure investigation, J. Phys. Chem. A, 1999, 103, 6257.
24. M. Moriyama, Y. Kawakami, S. Tobita and H. Shizuka, Intramolecular proton-transfer cycle of 2,4-dimethoxy-6-(1-hydroxy-2-naphthyl)-s-triazine studied by lazer photolysis, Chem. Phys., 1998, 231, 205.
25. D. Banerjee, A. Mandal and S. Mukherjee, Photoinduced proton transfer in the excited singlet state of 3,7-dihydroxynaphthoic acid and solvent effect, Chem. Phys. Lett., 2002, 357, 450.
26. M. Ikegami and T. Arai, Photoinduced intramolecular hydrogen atom transfer in 2-(2-hydroxyphenyl)benzoxazole and 2-(2-hydroxyphenyl)-benzothiazole studied by laser flash photolysis, J. Chem. Soc., Perkin Trans. 2, 2002, 7, 1296.
27. M. Obi, H. Sakuragi and T. Arai, Adiabatic intramolecular hydrogen atom transfer in 2-[2-(2-pyrrolyl)ethenyl]pyridine, Chem. Lett., 1998, 169.
28. T. Arai and K. Tokumaru, Photochemical one-way adiabatic isomerization of aromatic olefins, Chem. Rev., 1993, 93, 23.
29. 1p), J. Phys. Chem., 1981, 85, 1835.