Stereoselective synthesis of E, E / E, Z isomers based on 1-(4- iodophenyl)-2,5-divinyl-1H-pyrrole core skeleton: A configuration-controlled fluorescence characteristics and highly selective anti-cancer activity

Abstract

Abstract The E and Z isomeric intermediates based on ethyl/methyl-2-cyano-3-(5-formyl-1-(4-iodo-phenyl)-1H-pyrrol-2-yl)acrylate have been synthesized and these intermediates (E or Z) were further stereo-selectively converted into their respective E, E or E, Z isomers of diethyl/dimethyl-3,3 -(1-(4-iodophenyl)-1H-pyrrole-2,5-diyl)bis (2-cyanoacrylate) at the first time. The E, E isomers of both 2a and 3a, in solid state displayed higher quantum efficiency with longer fluorescent lifetime as compared to E, Z isomers. Notably, the E, E isomers proved to be better AIEs while, E, Z isomer of 2a has eminent anticancer activity against human nasopharyngeal carcinoma. A simple and straight forward strategy has been firstly developed to utilize the impact of configuration on fluorescence and anti-cancer activity.