In this work we present a comparative study on x-ray crystal structures, electrochemistry and optical properties of closely related oligothiophene derivatives endowed with either the strong electron acceptor dicyanovinyl (DCV) or tricyanovinyl (TCV) group. Both DCV and TCV groups play direct and crucial role in altering the solid state structures, redox behavior, and linear absorption and emission properties of oligothiophenes. Various synthetic routes used in the preparation of mono- and di- substituted thiophene derivatives will also be presented. The presence of TCV or DCV in oligothiophenes induces planarity, pi-stack formation and occasional syn conformations. Thiophenes containing these strong electron acceptors are highly colored and fluorescent. Cyclic voltammetry data suggest that the TCV group is a more efficient electron acceptor than the DCV, as evident from reduction peak potentials compared with the DCV group. Inter- and intra- molecular interactions in the crystal structures of these materials will be also highlighted.

Dicyanovinyl- and tricyanovinyl-oligothiophenes: A comparative study

245th National Meeting (2013)

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