Photoinitiated processes in 1-p-tolylsulfonylazo-2,4,6,8-tetrakis(tert-butyl)phenoxazine |
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| Authors: | Ivakhnenko T E Makarova N I Ivakhnenko E P Chuev I I Aldoshin S M Minkin V I Knyazhanskii M I |
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| Institution: | (1) Scientific Research Institute of Physical and Organic Chemistry, Rostov State University, 194/2 prosp. Stachki, 344090 Rostov-on-Don, Russian Federation;(2) Institute of Problems of Chemical Physics, Russian Academy of Sciences, 18 Institutskii prosp., 142432 Chernogolovka, Moscow Region, Russian Federation |
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| Abstract: | New photochromic compound 1-p-tolylsulfonylazo-2,4,6,8-tetrakis(tert-butyl)phenoxazine containing the intramolecular hydrogen bond NH...N and the corresponding model structures 2,4,6,8-tetrakis(tert-butyl)-1-(veratroylazo)phenoxazine and 2,4,6,8-tetrakis(tert-butyl)-N-acetyl-1-(p-tolylsulfonylazo)phenoxazine were synthesized and studied. The data obtained suggested the mechanism of the photoreaction resulting in the accumulation of betaine 1-hydroxy-2,4,6,8-tetrakis(tert-butyl)-10-tolylsulfonylphenoxazin-9-one. The photochromic transformations in the molecule under study are due to intramolecular proton phototransfer followed by E–Z-isomerization about the N–N bond and the formation of betaine 1-hydroxy-2,4,6,8-tetrakis(tert-butyl)-10-tolylsulfonylphenoxazin-9-one. The molecular and crystal structure of the photoproduct was studied by X-ray analysis. |
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| Keywords: | phenoxazine structurally flexible systems intramolecular proton phototransfer E– Z-isomerization molecular structure |
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