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Pure Appl. Chem., 1979, Vol. 51, No. 2, pp. 279-297

http://dx.doi.org/10.1351/pac197951020279

Cis-trans photoisomerization of 4-nitrostilbenes

D. Schulte-Frohlinde and H. Görner

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  • London Gábor, Chen Kuang-Yen, Carroll Gregory T., Feringa Ben L.: Towards Dynamic Control of Wettability by Using Functionalized Altitudinal Molecular Motors on Solid Surfaces. Chem. Eur. J. 2013, 19, 10690. <http://dx.doi.org/10.1002/chem.201300500>
  • Singh Chandralekha, Ghosh Rajib, Mondal Jahur A., Palit Dipak K.: Excited state dynamics of a push–pull stilbene: A femtosecond transient absorption spectroscopic study. Journal of Photochemistry and Photobiology A: Chemistry 2013, 263, 50. <http://dx.doi.org/10.1016/j.jphotochem.2013.04.027>
  • Lin Cheng-Kai, Wang Yu-Fu, Cheng Yuan-Chung, Yang Jye-Shane: Multisite Constrained Model of trans-4-(N,N-Dimethylamino)-4′-nitrostilbene for Structural Elucidation of Radiative and Nonradiative Excited States. J. Phys. Chem. A 2013, 117, 3158. <http://dx.doi.org/10.1021/jp310770s>
  • Rafiq Shahnawaz, Sen Pratik: Dielectric controlled excited state relaxation pathways of a representative push-pull stilbene: A mechanistic study using femtosecond fluorescence up-conversion technique. J. Chem. Phys. 2013, 138, 084308. <http://dx.doi.org/10.1063/1.4792933>
  • Megyesi Mónika, Biczók László, Görner Helmut, Miskolczy Zsombor: Effects of solvent polarity and hydrogen bonding on the fluorescence properties of trans-4-hydroxy-4′-nitrostilbenes. chem phys letts 2010, 489, 59. <http://dx.doi.org/10.1016/j.cplett.2010.02.050>
  • Görner Helmut, Megyesi Mónika, Miskolczy Zsombor, Biczók László: Photoproducts and triplet reactivity of 4′-nitro- and 2′,4′-dinitro-substituted 4-hydroxystilbenes. J Photochem Photobiol A Chem 2010, 214, 188. <http://dx.doi.org/10.1016/j.jphotochem.2010.06.025>
  • Pollard Michael M., Wesenhagen Philana V., Pijper Dirk, Feringa Ben L.: On the effect of donor and acceptor substituents on the behaviour of light-driven rotary molecular motors. Org Biomol Chem 2008, 6, 1605. <http://dx.doi.org/10.1039/b718294e>
  • Gurzadyan Gagik, Görner Helmut: Picosecond transient absorption spectroscopy of trans-4-R-4′-nitrostilbenes with R: OMe, NH2 and NMe2. chem phys letts 2000, 319, 164. <http://dx.doi.org/10.1016/S0009-2614(00)00097-X>
  • Görner Helmut: Photoprocesses in 4-nitro- and 2,4-dinitro-substituted trans-1-styrylnaphthalene, trans-9-styrylanthracene and related systems. J Photochem Photobiol A Chem 1999, 126, 15. <http://dx.doi.org/10.1016/S1010-6030(99)00122-7>
  • Görner Helmut: Photophysics and photochemistry of trans-4-nitrostilbenes and trans-2,4-dinitrostilbenes: Effect of intramolecular charge transfer. Berichte der Bunsengesellschaft für physikalische Chemie 1998, 102, 726. <http://dx.doi.org/10.1002/bbpc.19981020505>
  • Görner Helmut: Photolysis of trans-α,α′-dihalostilbenes. J Photochem Photobiol A Chem 1995, 90, 57. <http://dx.doi.org/10.1016/1010-6030(95)04066-O>
  • Unett D. J., Caldwell R. A.: The triplet state of alkenes: Structure, dynamics, energetics and chemistry. Res. Chem. Intermed. 1995, 21, 665. <http://dx.doi.org/10.1163/156856795X00639>
  • Mrozek Helga, Nikol Hans, Vogler Arnd, Vögtle Fritz: Photochemistry of barium(II) and lead(II) 2,4-dinitrostilbene-4′-monoaza-18-crown-6 complexes. J Photochem Photobiol A Chem 1994, 84, 227. <http://dx.doi.org/10.1016/1010-6030(94)03863-5>
  • Karatsu Takashi, Tsuchiya Masami, Arai Tatsuo, Sakuragi Hirochika, Tokumaru Katsumi: Features of the Quantum Chain Process in the Photochemical One-Way Isomerization of 2-Anthrylethylenes. Bull Chem Soc Jpn 1994, 67, 3030. <http://dx.doi.org/10.1246/bcsj.67.3030>
  • 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>
  • Meier Herbert: Die Photochemie stilbenoider Verbindungen und ihre materialwissenschaftlichen Aspekte. Angew Chem 1992, 104, 1425. <http://dx.doi.org/10.1002/ange.19921041104>
  • Görner Helmut, Fischer Ernst: Reversible photochemistry of 4-nitro-substituted diphenylazomethines. J Photochem Photobiol A Chem 1991, 57, 235. <http://dx.doi.org/10.1016/1010-6030(91)85019-D>
  • Kim Maeng Sup, Lee Ki Taek, Jeong Bong Mo, Lee Bok Hee, Shim Sang Chul: PHOTOCHEMICAL trans →cis ISOMERIZATION OF 6-STYRYLQUINOXALINE. Photchem Photbio 1991, 54, 517. <http://dx.doi.org/10.1111/j.1751-1097.1991.tb02051.x>
  • Bong Pill-Hoon, Lee Ki Taek, Shim Sang Chul, Hoshino Mikio: Laser flash photolysis study of 1-pyrazinyl-2-(4′-quinolinyl)ethylene. J Photochem Photobiol A Chem 1990, 53, 51. <http://dx.doi.org/10.1016/1010-6030(90)87112-O>
  • Justus B.L., Merritt C.D., Campillo A.J.: Efficient photogeneration of triplets in shock-compressed 2,4-dinitrostilbene. chem phys letts 1989, 156, 64. <http://dx.doi.org/10.1016/0009-2614(89)87082-4>
  • Shim Sang Chul, Lee Cheon Seok: Substituent effects on the photoisomerization of 5(E)-styryl-1,3-dimethyluracil. J Photochem Photobiol A Chem 1989, 50, 41. <http://dx.doi.org/10.1016/1010-6030(89)80019-X>
  • Wan Peter, Davis Michael J.: Photochemical tandem addition of water and oxygen to the alkene moiety of m-nitrostyrenes. J Photochem Photobiol A Chem 1989, 48, 387. <http://dx.doi.org/10.1016/1010-6030(89)87019-4>
  • Arai Tatsuo, Karatsu Takashi, Tsuchiya Masahiro, Sakuragi Hirochika, Tokumaru Katsumi: Triplet energy surfaces of one-way isomerizing olefins as studied by singlet oxygen luminescence technique. chem phys letts 1988, 149, 161. <http://dx.doi.org/10.1016/0009-2614(88)87214-2>
  • Misawa Hiroaki, Karatsu Takashi, Arai Tatsuo, Sakuragi Hirochika, Tokumaru Katsumi: A novel “across-a-ridge” isomerization of olefins. The energy surface of 2-ethenylanthracene in the excited triplet state. chem phys letts 1988, 146, 405. <http://dx.doi.org/10.1016/0009-2614(88)87467-0>
  • Görner Helmut, Elisei Fausto, Mazzucato Ugo, Galiazzo Guido: Trans → cis photoisomerization of 1-(1-naphthyl)-2-(4-nitrophenyl)ethylene. J Photochem Photobiol A Chem 1988, 43, 139. <http://dx.doi.org/10.1016/1010-6030(88)80014-5>
  • Elisei Fausto, Mazzucato Ugo, G��rner Helmut, Schulte-Frohlinde Dietrich: A laser flash photolysis study of the triplet state of trans-azastilbenes. Journal of Photochemistry 1987, 37, 87. <http://dx.doi.org/10.1016/0047-2670(87)85030-X>
  • Arai Tatsuo, Kuriyama Yasunao, Karatsu Takashi, Sakuragi Hirochika, Tokumaru Katsumi, Oishi Shigero: A new ���one-way���-photoisomerizing aromatic olefin: the effect of a fluoranthenyl group on the triplet energy surface. Journal of Photochemistry 1987, 36, 125. <http://dx.doi.org/10.1016/0047-2670(87)87068-5>
  • Görner Helmut: The cis—trans isomerization of nitrostilbenes XV: mixed singlet and triplet mechanism for trans → cis photoisomerization of 4-nitro-4′-dialkylaminostilbenes in non-polar solvents. J Photochem Photobiol A Chem 1987, 40, 325. <http://dx.doi.org/10.1016/1010-6030(87)85010-4>
  • Görner Helmut, Schulte-Frohlinde Dietrich: Photoinduced electron transfer from DABCO to trans-nitrostilbenes. chem phys letts 1986, 124, 321. <http://dx.doi.org/10.1016/0009-2614(86)85026-6>
  • Kobayashi Takayoshi, Ohtani Hiroyuki, Kurokawa Kenji: Picosecond time-resolved absorption and gain spectroscopy of a giant dipole molecule, 4-diethylamino-4′-nitrostilbene, in solution and in polymer film. chem phys letts 1985, 121, 356. <http://dx.doi.org/10.1016/0009-2614(85)87193-1>
  • G��rner Helmut, Gruen Henry: Photophysical properties of quaternary salts of 4-dialkylamino-4���-azastilbenes and their quinolinium analogues in solution: IX. Journal of Photochemistry 1985, 28, 329. <http://dx.doi.org/10.1016/0047-2670(85)85036-X>
  • Görner Helmut: Analysis of the Pathways for Cis ⇄ Trans Photoisomerization of 4-Nitro-,4,4′-Dinitro-, and 4-Nitro-4′-methoxystilbene in Solution. XII1. Berichte der Bunsengesellschaft für physikalische Chemie 1984, 88, 1199. <http://dx.doi.org/10.1002/bbpc.198400049>
  • Görner Helmut, Schulte-Frohlinde Dietrich: Laser Study of the Triplet State of 4-Nitrostilbenes in Solution; Estimation of the Equilibrium Constant (3 t* ⇄ 3 p*) and the Rate Constant for Intersystem Crossing (3 p* → 1 p). XIII1. Berichte der Bunsengesellschaft für physikalische Chemie 1984, 88, 1208. <http://dx.doi.org/10.1002/bbpc.198400050>
  • Görner H., Schulte-Frohlinde D.: Trans→cis photoisomerization of the quaternary iodides of 4-cyano- and 4-nitro-4′-azastilbene in ethanol solution: Singlet versus triplet mechanism. chem phys letts 1983, 101, 79. <http://dx.doi.org/10.1016/0009-2614(83)80309-1>
  • Knipe R.H., Fletcher A.N., Wolff Thomas, M��ller Norbert, Costanzo L.L., Pistar�� S., Giuffrida S., Condorelli G.: Effects of secondary chemical reactions upon the performance of dye lasers. Journal of Photochemistry 1983, 23, 117. <http://dx.doi.org/10.1016/0047-2670(83)80060-4>
  • Olbrich Gottfried: A Semi-Empirical Investigation into the Trans-Cis Photoisomerisation of Stilbene. Berichte der Bunsengesellschaft für physikalische Chemie 1982, 86, 209. <http://dx.doi.org/10.1002/bbpc.19820860307>
  • S��ez R��banos V., Tabar��s F., Gonz��lez Ure��a A., Costanzo L.L., Giuffrida S., Pistar�� S., Condorelli G., Abu-Zeid M.E., Marafi M.A., Nofal E.E., Anani A.A.: On the CN(B 2�� ��� X 2��) emission intensity in active nitrogen and carbon tetrachloride mixtures. Journal of Photochemistry 1982, 18, 301. <http://dx.doi.org/10.1016/0047-2670(82)87020-2>
  • De Haas Matthijs P., Warman John M.: Photon-induced molecular charge separation studied by nanosecond time-resolved microwave conductivity. Chemical Phys 1982, 73, 35. <http://dx.doi.org/10.1016/0301-0104(82)85148-3>
  • Burrows J.P., Cox R.A., Derwent R.G., G��rner H., Schulte-Frohlinde D., Mikuni Hitoshi, Takahasi Makoto: Modulated photolysis of the ozone���water vapour system: kinetics of the reaction of OH with HO2. Journal of Photochemistry 1981, 16, 147. <http://dx.doi.org/10.1016/0047-2670(81)80027-5>
  • G��rner Helmut: Author index. Journal of Photochemistry 1980, 13, 357. <http://dx.doi.org/10.1016/0047-2670(80)80020-7>