A novel homologous series of heterocyclic chalconyl esters (C-1 to C-16) has been synthesized and studied with a view to understanding and establishing the effects of molecular structure on liquid crystal (LC) properties and the degree of liquid crystallinity. The C-1 to C-6 homologues are not liquid crystals, the C-7 homologue is enantiotropic nematic, the C-8 to C-16 homologues are smectogenic in addition to nematogenic (C-8 & C-10 monotropic smectic). The texture of nematic phases are threaded or Schlieren and that of the smectic phase are fan-shaped smectic-A or smectic-C type. Transition temperatures and the textures of mesophases were determined by an optical polarizing microscope equipped with a heating stage. Transition curves Cr-I/M, Sm-N/N-Sm, and N-I showing phase behaviors of series in a phase diagram behave in normal manner. Thermal stability for smectic and nematic are 115.66 degrees C and 126.83 degrees C and their mesophase lengths minimum to maximum are 6.3 to 12.9 degrees C and 6.9 degrees C to 17.4 degrees C, respectively. Analytical and spectral data confirms the molecular structures of homologues. LC properties of present novel series are compared with structurally similar other reported series.