Supramolecular columnar self-assembly of wedge-shaped rhodanine based dyes: Synthesis and optoelectronic properties

Abstract

The development of small π-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.