Liquid crystalline polymers XV. Synthesis, properties and cytotoxicity of photoresponsive thermotropic liquid crystalline copoly(arylidene-ether)s based on 4-tert-butylcyclohexanone and cyclohexanone moieties in the main chain

Abstract

ABSTRACTA new series of photoresponsive thermotropic liquid crystalline copoly(arylidene-ether)s based on both 4-tert-butylcyclohexanone and cyclohexanone moieties in the main chain were synthesised using solution polycondensation technique of both with different 4,4ʹ-diformyl-α,ω-diphenoxyalkane derivatives. Two model compounds were synthesised from the reaction of each cycloalkanone monomer with benzaldehyde, and their structures were determined using single crystal X-ray diffraction. The structure of the monomers and copolymers was confirmed by elemental and spectral analyses. In addition, the thermal stabilities of these copolymers were evaluated by thermogravimetric analysis. We performed both differential scanning calorimertric and polarised optical microscopic measurements to investigate the thermotropic liquid crystalline properties of synthesised copolymers. The UV−Vis absorption spectroscopy of the liquid crystalline copoly(arylidene-ether) 6f revealed that the system undergoes Entgegen/Zusammen (E/Z) photoisomerisation using UV lamp (450 nm). Moreover, the various characteristics of the prepared copolymers including: solubility, X-ray diffraction analysis, gel permeation chromatography (GPC) and scanning electron microscopy were determined and discussed. The cytotoxicity of the model compounds and selected examples of these copolymers was tested against MCF-7 breast cancer cells. All tested samples showed considerable results, where 6c copolymer gave the best result; it showed cytotoxicity against MCF-7 cell line with IC50 of 0.26 µM.