Abstract
A procedure was developed for phase-transfer catalyzed alkylation of 5-hydroxyindolenine and 9"-hydroxy-substituted spiro[indoline-2,3"-naphtho[2,1-b]oxazines] by alkyl halides. New 9"-hydroxy- and 9"-alkoxy-substituted spironaphthooxazines, spirooxazinyloxyacetic acids, and their esters containing substituents with different length of the carbon chain in the indoline moiety were synthesized. The influence of the substituents on the spectroscopic properties of the starting and colored forms and the kinetic characteristics of photochromic transformations of 9"-substituted spironaphthooxazines in solutions and polymeric films was investigated. The bipolar merocyanine forms of spirooxazines were found to produce H-aggregates.
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Voloshin, N.A., Metelitsa, A.V., Micheau, JC. et al. Spiropyrans and spirooxazines. 1. Synthesis and photochromic properties of 9"-hydroxy- and 9"-alkoxy-substituted spironaphthooxazines. Russian Chemical Bulletin 52, 1172–1181 (2003). https://doi.org/10.1023/A:1024773727436
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DOI: https://doi.org/10.1023/A:1024773727436