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.