The "click" chemistry of cycloaddition/retroelectrocyclization reaction between activated alkynes by strong electron donating groups and strong electron accepting cyanoolefinic molecule (e.g., tetracyanoethylene (TCNE) and 7,7,8,8-tetracyanoquinodimethane (TCNQ)) are very effective in synthesizing main-chain donor-acceptor conjugated polymers via postfunctionalization. However, it remains a great challenge to fully complete this reaction in the main chain due to the decreased activity of main-chain alkynes after the adjacent ones are reacted with cyanoolefinic molecules. In this research, a main-chain poly(arylene ethynylene) precursor conjugated polymer, which has a dialkylanilino group in the para-position relative to each ethynyl group, was designed and synthesized. This precursor polymer was then reacted with TCNE via cycloaddition/retroelectrocyclization reaction in a quantative yield to afford a main-chain donor-acceptor conjugated polymer. This conjugated polymer exhibits a low bandgap energy (Egopt = 1.40 eV and EgCV = 1.10 eV), due to the intramolecular charge-transfer interactions between electron donors and acceptors alternating along the macromolecular chain.

Main-chain donor-acceptor conjugated polymers by "click" chemistry

2019 Fall National Meeting

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