The “click” type reaction of strong electron acceptors such as tetracyanoethylene (TCNE) and 7,7,8,8-tetracyanoquinodimethane (TCNQ) with electron-rich alkynes gives donor-acceptor derivatives in a quantitative yield. The fundamental mechanism behind this is attributed to the fact that the electron accepting TCNE or TCNQ undergoes thermal [2+2] cycloaddition with electron<b>-</b>rich alkynes followed by spontaneous electrocyclic ring opening of the initially formed cyclobutenes. This cycloaddition/retroelectrocyclization reaction was used to synthesize novel donor-acceptor type polymers. The strong intramolecular charge-transfer interactions of these polymers resulted in low bandgaps and enhanced thermal stability. These donor-acceptor polymers promise as potential applications in nonlinear optical device, organic photovoltaic devices, and light emitting diodes.

Synthesis of donor-acceptor type polymers by click chemistry of cycloaddition/retroelectrocyclization

252nd National Meeting (2016)

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