Synthesis and studies of new photochromic spiropyrans containing a formylcoumarin fragment

Abstract

A computer search for new photoactive compounds among indoline spiropyrans of coumarin series was carried out using DFT B3LYP/6-31G(d,p) method. Based on the data obtained, the spiropyrans containing a formylcoumarin fragment annulated to the 2H-pyran ring and possessing photochromic properties were synthesized. The structure and photochromism of these compounds were studied by ¹H NMR, IR, and UV/Vis spectroscopy. The introduction of a formyl group into the coumarin moiety of spiropyrans led to a bathochromic shift of the long wavelength absorption maxima of merocyanine isomers, as well as to a considerable increase in their lifetime.