Dependence of mesomorphism on tail group in combination with a lateral methoxy group

A novel homologous series of esters with a lateral methoxy group and terminal n-heptyl cinnamate group was synthesized and studied to investigate mesomorphic behavior in relation to structure. The twelve membered series consists of methoxy to pentyloxy derivatives that are nonmesomorphic and the rest of the homologs as smectegenically mesomorphic, including C₆ and C₇ monotropic smectic and C₈ to C₁₆ enantiotropic smectic without exhibition of any nematic property. The textures of smectogenic mesophases are focal conic fan shaped or batonates of the type smectic-A or Schlieren-C. An odd-even effect is exhibited by the Sm–I transition curve in the phase diagram. The Cr–Sm and Sm-I transition curves behave in a normal manner. Transition temperatures and textures were determined on an optical polarizing microscope, equipped with a heating stage. Some representative members were characterized by IR, H¹NMR, mass spectra, and elemental analysis. Analytical data support the molecular structures of the homologs. Mesomorphic properties of the present novel series are compared with the structurally similar known series. The present series is smectogenic only, whose thermal average stability is 89.8^°C and of a middle-ordered melting type.