Synthesis, characterization and crystal structure of mesogenic compounds with an alkyloxy and a semi-perfluorinated chain. Influence of the alkyloxy chain length on molecular arrangement and molecular interactions

Abstract

This paper describes the synthesis and study of the mesomorphic properties (by DSC, microscopic observation and X-ray diffraction) of three new series of semi-perfluorinated liquid crystals: 4-(2,2,3,3,4,4,4-heptafluorobutyloxycarbonyl)phenyl, 4-(2,2,3,3,4,4,5,5-octafluoropentyloxycarbonyl)phenyl, and 4-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-octyloxy-carbonyl)phenyl 4-(n-alkyloxy)benzoates. One compound of the second family crystallizes in the P1 space group with Z ' 2. The molecule adopts a slightly bent conformation with a fully extended alkyloxy and semi-perfluorinated chain in a smectic C-like structure. The comparison of the present structure is made with that of a similar compound of the first family with a longer alkyloxy chain (this latter crystallizes in the P1 space group with two independent molecules in the unit cell). Comparison of the molecular packing shows the importance of the chain lengths in the molecular arrangement and molecular interactions in both structures.