Benzoladderene Mechanophores: Synthesis, Polymerization, and Mechanochemical Transformation.
Jinghui YangMatías HorstJoseph A H RomaniukZexin JinLynette CegelskiYan XiaPublished in: Journal of the American Chemical Society (2019)
We have previously reported a polymechanophore system, polyladderene, which underwent dramatic bond rearrangement in response to mechanical force to yield semiconducting polyacetylene. Herein, we report the scalable synthesis of benzoladderenes as new mechanophore monomers. Ring-opening metathesis polymerization of benzoladderenes yielded homopolymers and block copolymers with controlled molecular weights and low dispersity. The resulting nonconjugated poly(benzoladderene) was mechanochemically transformed into conjugated poly( o-phenylene-hexatrienylene) by sonication, with degrees of transformation up to 40-45%. These benzoladderenes and their resulting polymers are easier to synthesize than the polyladderene system and allow mechanochemical generation of conjugated polymers beyond polyacetylene.
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