Vinayakumara, D.R.Kumar, S.Vasudeva Adhikari, A.V.2026-02-052019Journal of Molecular Liquids, 2019, 274, , pp. 215-2221677322https://doi.org/10.1016/j.molliq.2018.10.139https://idr.nitk.ac.in/handle/123456789/24728The development of small ?-conjugated functional organic molecules capable of forming supramolecular columnar self-assembly, is a rapidly growing area of material research. In this context, the present work describes the design and synthesis of a new series of wedge-shaped rhodanine derivatives with D-A configuration, viz. RA1–RA5. Their LC properties were studied by employing DSC, POM and XRD techniques. The mesophase behavior was investigated as a function of chain length, density and position of alkoxy terminals to understand structure-property relationship. Interestingly, the longer chain analog, i.e. RA3 demonstrated H-bonded disc-like macrocyclic structures, causing an imperative columnar hexagonal phase at ambient temperature. Further, their photophysical and electrochemical properties were evaluated. They showed a good dye property attributing to effective intramolecular interactions, as confirmed by experimental and theoretical studies. Conclusively, RA3 has been considered to be a potential candidate for its application in organic electronics. © 2018ChainsDyesHydrogen bondsSupramolecular chemistryThermotropic liquid crystalsColumnar hexagonal phaseHeterocyclesIntramolecular interactionsMacrocyclic structureMesophase behaviorOptoelectronic propertiesOrganic electronicsStructure property relationshipsSelf assembly