Photoinitiated processes in 1-p-tolylsulfonylazo-2,4,6,8-tetrakis(tert-butyl)phenoxazine

Citation
Te. Ivakhnenko et al., Photoinitiated processes in 1-p-tolylsulfonylazo-2,4,6,8-tetrakis(tert-butyl)phenoxazine, RUSS CHEM B, 49(12), 2000, pp. 1981-1987
Citations number
13
Categorie Soggetti
Chemistry
Journal title
RUSSIAN CHEMICAL BULLETIN
ISSN journal
10665285 → ACNP
Volume
49
Issue
12
Year of publication
2000
Pages
1981 - 1987
Database
ISI
SICI code
1066-5285(200012)49:12<1981:PPI1>2.0.ZU;2-J
Abstract
New photochromic compound 1-p-tolylsulfonylazo-2,4,6,8-tetrakis(tert-butyl) phenoxazine containing the intramolecular hydrogen bond NH . . .N and the c orresponding 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-h ydroxy-2,4,6,8-tetrakis(tert-butyl)-10-tolylsulfonylphenoxazin-9-one. The p hotochromic transformations in the molecule under study are due to intramol ecular proton phototransfer followed by E-Z-isomerization about the N-N bon d and the formation of betaine 1-hydroxy-2,4,6,8-tetrakis(tert-butyl)-10-to lylsulfonylphenoxazin-9-one. The molecular and crystal structure of the pho toproduct was studied by X-ray analysis.