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
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.