Enhanced functionality for donor-acceptor oligothiophenes via Inclusion of BODIPY : synthesis, electrochemistry, photophysics and model chemistry

Abstract

We have synthesized several new push-pull oligothiophenes based on the BODIPY moiety as the electron acceptor and the well known oligothiophenes substituted with N,N-dialkylamino groups to enhance the electron donor ability. A complete characterization of the electronic properties has been done consisting of their photophysical, electrochemical and vibrational properties. The compounds have been studied after chemical treatment with acids and after oxidation. In this regard, they can be termed as NIR dyes and amphoteric redox electroactive molecules. We have described the presence of dual fluorescence in these molecules and fluorescence quenching either by energy transfer or, in the push-pull molecules, by the electron exchange. The combination of electrochemical and proton reversibility combined with the interesting optical properties of the new species offer an interesting platform for sensor and material applications.