Highly Branched Alkanoic Acids from the Preen-Gland Wax of the Domestic Goose as Building Blocks for Chiral Triphenylenes

Abstract

The synthesis of chiral triphenylenes 7a,b bearing side chains derived from enantiomerically pure trimethyloctanoate 1a and tetramethyldecanoate 1b from the preen-gland wax of domestic goose was achieved in 3 or 4 steps. Compounds 7a,b were nonmesogenic; however, mixtures of 7a,b with hexakis(octyloxy)triphenylene or hexakis(decyloxy)triphenylene displayed columnar mesophases or soft crystal G phases, as was shown by differential-scanning calorimetry and optical-polarizing microscopy. Circular-dichroism measurements revealed weak associations of 7a,b in solution.