Synthesis of new chiral smectic mesogenes with 4-(2-Phenylethyl)biphenyl and 4-[2-(3-Fluorophenyl)ethyl]biphenyl Molecular Cores

Article abstract of DOI:10.1055/s-0029-1219833

Two methods of synthesis of chosen 1-[4-(1-methyl-heptyloxycarbonyl)phenyl] -2-[4′-(2,2,3,3,4,4,4-heptafluorobutoxyalkoxy)biphenyl-4-yl]ethanes and 1-[3-fluoro-4-(1-methylheptyloxycarbonyl)phenyl]-2-[4′-(2,2,3,3,4,4, 4-heptafluorobutoxyalkoxy)bi-phenyl-4-yl]ethanes have been proposed, checked and compared. The compounds were prepared by Sonogashira coupling of 4-benzyloxy-4′-ethynylbiphenyl with appropriate 4-halobenzoate esters followed by parallel hydrogenation of ethynylene bridge and debenzylation of hydroxyl group. The 1-[4-(1-methylheptyloxycarbonyl)phenyl]-2-[4′- hydroxybiphenyl-4-yl]ethane and 1-[3-fluoro-4-(methoxycarbonyl)phenyl]-2- [4′-hydroxybiphenyl-4-yl]ethane thus obtained has been transformed into final products by Mitsunobu reaction with ω-(2,2,3,3,4,4,4- heptafluorobutoxy)alkan-1-ols, followed by the replacing of an ester terminal chain in the case of second method.