Highly selective discriminating E, E/E, Z isomers of functionalized 1-phenyl-2,5-divinyl-1H-pyrrole for n-/sec-/tert-butyl amines and as temperature sensor

Abstract

A series of novel E, E/E, Z isomers based on 5-(2-cyano-3-ethoxy-3-oxoprop-1-en-1-yl)-1H-pyrrol-2-yl acrylic acid have been successfully synthesized. The comparative studies between compounds presenting E, E/E, Z isomers on the properties of emission and effects of temperature had been discussed. Interestingly, the E, Z, and E, E isomers emitted different luminous colors and aggregation-induced emission (AIE) properties. Notably, the E, Z-OC2H5COOH and E, E-OC2H5COOH loaded on filter paper could identify alkaline compounds. Furthermore, E, E-OC2H5COOH strips could selectively discriminate for n-/sec-/tert-butylamine by changing the color of the fluorescence. In addition, E, E-OC2H5COOH, doped into polymer dimethyl silicone (PDMS) film could exhibit an evident change in emission color from orange to yellow at 90 °C and gradually vanished at 190 °C, while that of E, Z-OC2H5COOH didn't change significantly with heating. Therefore, the configuration of two double bonds can be used to regulate the change of fluorescence, improve the chemical and physical properties of materials, and break through the deficiency of single configuration regulation.