SYNTHESIS AND STRUCTURAL CHARACTERIZATION OF NEW SPIROPYRAN CONTAINING CONJUGATED VINYL-3Н-INDOLIUM MOIETY AND ITS HYDROLYSIS PRODUCT

Abstract

A new spiropyran containing a cationic 3Н-indolium substituent and methoxy groups at positions 5 and 5'' of the indoline cycles was synthesized. Hydrolysis of this compound was observed during crystallization from EtOH, leading to the formation of protonated merocyanine form of spiropyran containing a free formyl group. The hydrolysis product was characterized by X-ray structural analysis, the intermolecular interactions in crystal were studied with the CrystalExplorer 21.5 software suite. Quantum-chemical modeling based on the Fukui function distribution was used to establish the preferred site for nucleophilic attack, and a mechanism for hydrolysis was proposed.

Authors: Anastasia S. Kozlenko, Artem D. Pugachev, Ilya V. Ozhogin, Valery V. Tkachev, Vladislav V. Bykusov, Natalia V. Stankevich, Sergei M. Aldoshin, Vladimir I. Minkin1, Boris S. Lukyanov*