Photochromism of 1′,3′,3′-trimethyl-6-piperidinospiro [indoline-2′,3-3H-naphth [2,1-b][1,4]-oxazine]

The effect of the piperidine substituent on the spectral and photochromic properties of spiro(indoline-naphthoxazines) (SINO) in different solvents is studied. The introduction of this substituent into the naphthoxazine fragment of SINO results in the appearance of fluorescence of the initial formA of SINO at low temperatures. This fluorescence gradually disappears as the temperature increases. The temperature and concentration dependences of the spectral parameters of photoinduced formB of SINO make it possible to assume thatB molecules aggregate in non-polar solvents. In all solvents studied, form B, unlike the photoinduced form of the non-substituted spiro naphthoxazine, is stabilized as a bipolar ion with a positive charge on the nitrogen atom of the piperidine substituent. The increase in the rate of thermal decolorization as the medium polarity increases is explained.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 684–688, April, 1995.The authors are grateful to the Belarus' Foundation for Basic Research for financial support of this work.