Saddle-shaped tetraphenylenes with peripheral gallic esters displaying columnar mesophases

Tetraphenylenes 2 with eight peripheral gallic esters were prepared in two steps from octamethoxytetraphenylene 1 in 19–72% yield. Investigation of the mesomorphic properties of 2 by DSC, POM and X-ray diffraction revealed that derivatives 2a – d with short alkoxy chain lengths (C 5 –C 8 ) did not show any mesomorphic properties, whereas compounds 2e – i with C 9 –C 13 chains displayed rectangular columnar mesophases and compounds 2j – l with C 14 –C 16 chains displayed hexagonal columnar mesophases. Furthermore an anomalous odd-even effect of the clearing points of compounds 2e – l versus chain length was detected.

Abstract licence: CC BY

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