Synthesis and mesomorphic properties of 2,6-disubstituted derivatives of quinoline: amides and esters

Thesyntheses of N-4-n-alkoxyphenyl-6-n-decyloxyquinoline-2-carboxamide(alkoxy=CnH2n+1O, n=4-10) and 4-n-alkoxyphenyl-6-n-decyloxyquinoline-2-carboxylate (n=4,6,8) are described along with the measurement of their physical properties using DSC and optical methods. The amides all show an enantiotropic smectic A phase while the esters show monotropic mesophases. A study of the structure/mesomorphic activity relationship is also described.