Synthesis and mesomorphic properties of 7‐acyloxy‐3‐(4‐acyloxyphenyl)‐4H‐1‐benzopyran‐4‐one

Abstract

A new homologous series of 7‐acyloxy‐3‐(4‐acyloxyphenyl)‐4H‐1‐benzopyran‐4‐ones was synthesized and characterized by elemental analysis and spectroscopic techniques along with thermal behaviour study using differential scanning calorimetry. Texture observation was performed under the polarizing optical microscope from which the derivatives were found to exhibit different molecular organizations as exemplified by various mesophases. Whilst the compounds containing butanoyloxy and hexanoyloxy groups behave as nematogens, the other compounds with heptanoyloxy and longer side chains show a SmC phase. The octadecanoyloxy derivative was the only member showing a monotropic SmC phase. The difference in phase behaviour is discussed based on the molecular structure and the presence of a lateral dipole which can be associated with the intermolecular interaction within the mesophase.

Acknowledgements

G.‐Y.Y. would like to thank Universiti Sains Malaysia for USM Short‐Term Grant No. 304/PKIMIA/636103, and the Soka University, Japan, for providing partial funding through the Open Research Project.