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Benzoladderene Mechanophores: Synthesis, Polymerization, and Mechanochemical Transformation

Author:
Yang, Jinghui, Horst, Matias, Romaniuk, Joseph A. H., Jin, Zexin, Cegelski, Lynette, Xia, Yan
Source:
Journal of the American Chemical Society 2019 v.141 no.16 pp. 6479-6483
ISSN:
1520-5126
Subject:
composite polymers, forces, mechanochemistry, molecular weight, polyacetylenes, polymerization, sonication
Abstract:
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.
Agid:
6377240