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Pure Appl. Chem., 1988, Vol. 60, No. 7, pp. 989-998

http://dx.doi.org/10.1351/pac198860070989

Novel insights into photoisomerization of olefins

T. Arai, T. Karatsu, H. Misawa, Yasunao Kuriyama, H. Okamoto, Tatsuro Hiresaki, Hideo Furuuchi, Hualing Zeng, H. Sakuragi and K. Tokumaru

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  • Karatsu Takashi, Itoh Hajime, Yoshikawa Nobuko, Kitamura Akihide, Tokumaru Katsumi: Rotational Isomerization of (E)-(2-Anthryl)ethenes. A Consideration Why Are the s-cis Rotamers More Stable than the s-trans Rotamers in the Excited State and Less Stable in the Ground State?. Bull Chem Soc Jpn 1999, 72, 1837. <http://dx.doi.org/10.1246/bcsj.72.1837>
  • Tokumaru Katsumi: Design of Conjugated Aromatic Unsaturated Molecules for Photonics to Control Trans to cis Isomerization Under Irradiation. Molecular Crystals and Liquid Crystals Science and Technology Section A Molecular Crystals and Liquid Crystals 1998, 322, 277. <http://dx.doi.org/10.1080/10587259808030234>
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  • Arai Tatsuo, Yuda Yoshihiko, Sano Katsunori: One-way isomerization and internal rotation in anthrylethylenes in the excited triplet state. Res. Chem. Intermed. 1995, 21, 961. <http://dx.doi.org/10.1163/156856795X00602>
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  • Tokumaru Katsumi, Arai Tatsuo: Factors Determining the Adiabatic or the Diabatic Pathway of the Photoisomerization of Unsaturated Bonds. Bull Chem Soc Jpn 1995, 68, 1065. <http://dx.doi.org/10.1246/bcsj.68.1065>
  • Nakabayashi Kenichi, Ohashi Kyouko, Takamuku Setsuo: Conformation of Methyl trans-3-Arylpropenoates in Triplet States and Their Reactivities. Bull Chem Soc Jpn 1994, 67, 1201. <http://dx.doi.org/10.1246/bcsj.67.1201>
  • Karatsu Takashi, Kitamura Akihide, Arai Tatsuo, Sakuragi Hirochika, Tokumaru Katsumi: Photochemical Cis to Trans One-Way Isomerization of Styrylazulenes on Their Triplet Excited State. Examination of Ethylenes with Non-Benzenoid Substituents of Low Triplet Energies. Bull Chem Soc Jpn 1994, 67, 1674. <http://dx.doi.org/10.1246/bcsj.67.1674>
  • Karatsu Takashi, Arai Tatsuo, Sakuragi Hirochika, Tokumaru Katsumi, Wirz Jakob: Semiempirical Calculation of the Triplet-Triplet Absorption Spectra of 2-Anthrylethylenes Undergoing Photochemical One-Way Isomerization. Bull Chem Soc Jpn 1994, 67, 891. <http://dx.doi.org/10.1246/bcsj.67.891>
  • Arai Tatsuo, Takahashi Osamu, Asano Tomoyuki, Tokumaru Katsumi: The Effect of Substitution of 3-Perylenyl Group, an Aromatic Nucleus with a Very Low Triplet Energy, on Photochemical Isomerization of the Unsaturated Bond. Direct Observation of Triplet State Isomerization of a Styrene Derivative. Chem Lett 1994, 205. <http://dx.doi.org/10.1246/cl.1994.205>
  • Karatsu Takashi, Yoshikawa Nobuko, Kitamura Akihide, Tokumaru Katsumi: Rotational Isomerization of trans-2-Styrylanthracene between (s)-trans and (s)-cis Rotamers in the Excited States. Investigation of Its Sterically Restricted Model Compounds. Chem Lett 1994, 381. <http://dx.doi.org/10.1246/cl.1994.381>
  • Karatsu Takashi, Shiga Tsutomu, Kitamura Akihide, Arai Tatsuo, Sakuragi Hirochika, Tokumaru Katsumi: Effect of Substitution of a 2-Anthryl Group at the N=N and N=C Unsaturated Bonds on Their Photoisomerization in the Triplet State. Chem Lett 1994, 825. <http://dx.doi.org/10.1246/cl.1994.825>
  • Mazzucato U., Aloisi G. G., Elisei F.: Cis-trans photoisomerization of 1,2-diarylethylenes: Effect of charge transfer interactions. J Chem Sci 1993, 105, 475. <http://dx.doi.org/10.1007/BF03040819>
  • Sun Licheng, Görner Helmut: Trans → cis photoisomerization of 1-(9-anthryl)-2-(4-R-phenyl)ethylene, R: CH3 and OCH3. chem phys letts 1993, 208, 43. <http://dx.doi.org/10.1016/0009-2614(93)80074-Y>
  • Arai Tatsuo, Furuya Yasunori, Furuuchi Hideo, Tokumaru Katsumi: One-way Z→E isomerization around the double bond of N-methoxy- 1- (2-anthryl) ethanimine in the excited triplet state. Direct observation of one-way isomerization from Z triplet to E triplet of the CN bond. chem phys letts 1993, 212, 597. <http://dx.doi.org/10.1016/0009-2614(93)85491-6>
  • Mazzucato Ugo, Spalletti Anna, Bartocci Giampiero, Galiazzo Guido: Evidence of adiabatic channels in the singlet photoisomerization of cis-1,2-diarylethenes: a fluorimetric study. Coord Chem Rev - 1993, 125, 251. <http://dx.doi.org/10.1016/0010-8545(93)85022-V>
  • Arai Tatsuo, Okamoto Hiroaki, Tokumaru Katsumi, Ni Tuqiang, Caldwell R.A., Ueno Katsuhiko: Potential energy surfaces of a one-way photoisomerizing olefin studied by photoacoustic calorimetry and X-ray crystallography. J Photochem Photobiol A Chem 1993, 75, 85. <http://dx.doi.org/10.1016/1010-6030(93)80187-E>
  • Gritsan N.P., Klimenko L.S.: Photochromism of quinoid compounds: Properties of photo-induced ana-quinones. J Photochem Photobiol A Chem 1993, 70, 103. <http://dx.doi.org/10.1016/1010-6030(93)85030-C>
  • Kanna Yoko, Arai Tatsuo, Tokumaru Katsumi: Photoisomerization of Bilirubins and the Role of Intramolecular Hydrogen Bonds. Bull Chem Soc Jpn 1993, 66, 1482. <http://dx.doi.org/10.1246/bcsj.66.1482>
  • Segawa Katsunori, Takahashi Ohgi, Kikuchi Osamu, Arai Tatsuo, Tokumaru Katsumi: Ab Initio Triplet Potential Energy Curves of Methyl-Substituted Arylethylenes along the Double Bond Twisting. Bull Chem Soc Jpn 1993, 66, 2754. <http://dx.doi.org/10.1246/bcsj.66.2754>
  • Nakabayashi Kenichi, Tahara Yasuhisa, Yasuda Masahide, Shima Kensuke, Takamuku Setsuo: Cycloreversion of Aryl-Substituted Cyclobutene by Direct Photolysis and Pulse Radiolysis. Bull Chem Soc Jpn 1993, 66, 698. <http://dx.doi.org/10.1246/bcsj.66.698>
  • Kikuchi Yoshihiko, Okamoto Hiroaki, Arai Tatsuo, Tokumaru Katsumi: Effect of Acetonitrile Completely Suppressing Trans-to-cis Photoisomerization of Styrylpyrene Substituted with a Nitro Group. Chem Lett 1993, 1811. <http://dx.doi.org/10.1246/cl.1993.1811>
  • Arai Tatsuo, Iwasaki Takeshi, Tokumaru Katsumi: Trans.RAR.cis One-way Photoisomerization of an Olefin Substituted with an Indole and a Pyridine Ring. Effect of Intramolecular Hydrogen Bond. Chem Lett 1993, 691. <http://dx.doi.org/10.1246/cl.1993.691>
  • Gong Yuefa, Arai Tatsuo, Tokumaru Katsumi: One-Way Photoisomerization of Dienes Substituted by an Anthracene Nucleus. Chem Lett 1993, 753. <http://dx.doi.org/10.1246/cl.1993.753>
  • Kikuchi Yoshihiko, Okamoto Hiroaki, Arai Tatsuo, Tokumaru Katsumi: Effect of Substituents on the Equilibrium between Trans and Perpendicular Conformers in the Triplet Excited State of Substituted Styrylpyrenes. Chem Lett 1993, 833. <http://dx.doi.org/10.1246/cl.1993.833>
  • Meier Herbert: Die Photochemie stilbenoider Verbindungen und ihre materialwissenschaftlichen Aspekte. Angew Chem 1992, 104, 1425. <http://dx.doi.org/10.1002/ange.19921041104>
  • Arai Tatsuo, Ogawa Yasushi, Sakuragi Hirochika, Tokumaru Katsumi: Inefficient “one-way” isomerization of cis-styrylferrocene. Suppression of cis—trans isomerization by heavy-atom-induced intersystem crossing. chem phys letts 1992, 196, 145. <http://dx.doi.org/10.1016/0009-2614(92)85944-6>
  • Tokumaru Katsumi, Arai Tatsuo: Potential energy surfaces of one-way and two-way photoisomerization of olefins. J Photochem Photobiol A Chem 1992, 65, 1. <http://dx.doi.org/10.1016/1010-6030(92)85026-Q>
  • Arai Tatsuo, Karatsu Takashi, Sakuragi Hirochika, Tokumaru Katsumi, Tamai Naoto, Yamazaki Iwao: Effects of β-substituents on internal rotation of the anthryl group of 2-anthrylethylenes in the excited singlet state. J Photochem Photobiol A Chem 1992, 65, 41. <http://dx.doi.org/10.1016/1010-6030(92)85030-X>
  • Lednev Igor K., Alfimov Michael V., Kuriyama Yasunao, Arai Tatsuo, Sakuragi Hirochika, Tokumaru Katsumi: Photosensitized cis—trans isomerization of stilbene via cation radical mechanism in micellar solution. J Photochem Photobiol A Chem 1992, 63, 201. <http://dx.doi.org/10.1016/1010-6030(92)85137-J>
  • Kikuchi Osamu, Segawa Katsunori, Takahashi Ohgi, Arai Tatsuo, Tokumaru Katsumi: Qualitative Triplet Potential Energy Curves of Arylethylenes along the Double Bond Twisting. Bull Chem Soc Jpn 1992, 65, 1463. <http://dx.doi.org/10.1246/bcsj.65.1463>
  • Nakabayashi Kenichi, Takamuku Setsuo: Triplet Sensitized Quadricyclane-Norbornadiene Valence Isomerization of Methyl 5-(4-Biphenylyl)tetracyclo-(3.2.0.2,70.4,6)heptane-1-carboxylate. Bull Chem Soc Jpn 1992, 65, 3177. <http://dx.doi.org/10.1246/bcsj.65.3177>
  • Karatsu Takashi, Kitamura Akihide, Zeng Hauling, Arai Tatsuo, Sakuragi Hirochika, Tokumaru Katsumi: Effects of Substitution with Positionally isomeric Anthryl Groups on the One-Way Isomerization. Chem Lett 1992, 2193. <http://dx.doi.org/10.1246/cl.1992.2193>
  • Spalletti Anna, Bartocci Giampiero, Mazzucato Ugo, Galiazzo Guido: Decay pathways of the first excited singlet state of cis-1-styrylpyrene. chem phys letts 1991, 186, 297. <http://dx.doi.org/10.1016/S0009-2614(91)85145-M>
  • Karatsu Takashi, Tsuchiya Masami, Arai Tatsuo, Sakuragi Hirochika, Tokumaru Katsumi: Spectroscopic evidence for an energy minimum at the cis geometry of the triplet state of a butenylanthracene. Further insight into across-a-ridge isomerization of anthrylethylenes. chem phys letts 1990, 169, 36. <http://dx.doi.org/10.1016/0009-2614(90)85161-5>
  • Sundahl Mikael, Sandros Kjell, Wennerström Olof, Arai Tatsuo, Okamoto Hiroaki, Tokumaru Katsumi: One-way isomerization of a [26]orthoparacyclophene: Spectroscopic evidence for adiabatic sixfold Z/E-photoisomerization. chem phys letts 1990, 168, 395. <http://dx.doi.org/10.1016/0009-2614(90)85631-L>
  • Furuuchi Hideo, Arai Tatsuo, Kuriyama Yasunao, Sakuragi Hirochika, Tokumaru Katsumi: One-way photoisomerization of the C=N double bond. Isomerization of (Z)-N-methoxy-1-(2-anthryl)ethanimine. Chem Lett 1990, 847. <http://dx.doi.org/10.1246/cl.1990.847>
  • Jiang Jian, Kobayashi Eiichi, Aoshima Sadahrto, Furukawa Junji: Novel Conjugated Polymer Containing Anthracene Backbone: The Microstructure of Polymer Composed of 1,4-Benzenedithiol with 9,10-Diethynylanthracene and Isomerization of the Polymer and Model Compounds. Polym J 1990, 22, 274. <http://dx.doi.org/10.1295/polymj.22.274>
  • Furuuchi Hideo, Arai Tatsuo, Kuriyama Yasunao, Sakuragi Hirochika, Tokumaru Katsumi: Factors distinguishing one-way and two-way photoisomerization of aromatic olefins. Effects of substituents on triplet energy surfaces of 8-fluoranthenylethylenes. chem phys letts 1989, 162, 211. <http://dx.doi.org/10.1016/0009-2614(89)85126-7>
  • Hashimoto Hideki, Koyama Yasushi, Ichimura Kouichi, Kobayashi Takayoshi: Time-resolved absorption spectroscopy of the triplet state produced from the all-trans, 7-cis, 9-cis, 13-cis, and 15-cis isomers of β-carotene. chem phys letts 1989, 162, 517. <http://dx.doi.org/10.1016/0009-2614(89)87017-4>
  • Arai Tatsuo, Okamoto Hiroaki, Sakuragi Hirochika, Tokumaru Katsumi: Mechanism for photoisomerization of 1-styrylpyrene. Finding of a novel type of triplet energy surface with two decay funnels. chem phys letts 1989, 157, 46. <http://dx.doi.org/10.1016/0009-2614(89)87205-7>