Synthesis, structure and photochromic properties of novel highly functionalized spiropyrans of 1,3-benzoxazin-4-one series
Abstract
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.
- Publication:
-
Journal of Molecular Structure
- Pub Date:
- June 2018
- DOI:
- 10.1016/j.molstruc.2018.02.027
- Bibcode:
- 2018JMoSt1161...18O
- Keywords:
-
- Spiropyrans;
- Photochromism;
- Merocyanines;
- Molecular switches;
- 1;
- 3-benzoxazines;
- Single crystal X-ray analysis