Synthesis, structure and photochromic properties of novel highly functionalized spiropyrans of 1,3-benzoxazin-4-one series

Add time:09/10/2019    Source:sciencedirect.com

Based on a new polyfunctional derivative of dihydroxyisophtalic aldehyde (1) spiropyrans of 1,3-benzoxazin-4-one series with two carbonyl and a hydroxygroup in the [2H]-chromene fragment were synthesized. The results of single crystal X-ray analysis of 6′-carbomethoxy-3,5-dimethyl-8′-formyl-5′-hydroxy-4-oxospiro[1,3-benzoxazine-2,2′-chromene] (7a) helped to establish that condensation of 1,3-benzoxazine-4-onium perchlorates with (1) leading to the formation of spiropyrans occurs on the formyl group located at the position 3 of the starting aldehyde. The obtained spropyrans demonstrate photochromic activity at room temperature. Introduction of an electron donating methoxy group into the heteroarene part of the spiropyran molecule enhances its photocolorability.

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