Bicyclohexene-peri-naphthalenes: Scalable Synthesis, Diverse Functionalization, Efficient Polymerization, and Facile Mechanoactivation of Their Polymers

• DOI: 10.1021/jacs.0c06454
• Publication Date: 2020-07-30T12:18:38Z
• Authors: Jinghui Yang; Maggie Horst; Sabrina H. Werby; Lynette Cegelski; Noah Z. Burns; Yan Xia
• Keywords: ROMP; Dispersity; Surface Modification

Pursuing polymers that can transform from a nonconjugated to conjugated state under mechanical stress significantly change their properties, we developed new generation of ladder-type mechanophore monomers, bicyclo[2.2.0]hex-5-ene-peri-naphthalene (BCH-Naph), be directly and efficiently polymerized by ring-opening metathesis polymerization (ROMP). BCH-Naphs synthesized in multigram quantities functionalized with wide range electron-rich electron-poor substituents, allowing tuning the optoelectronic physical properties mechanically generated polymers. Efficient ROMP yielded ultrahigh molecular weight polymechanophores controlled MWs low dispersity. The resulting poly(BCH-Naph)s activated into using ultrasonication, grinding, even simple stirring dilute solutions, leading changes absorption fluorescence. Poly(BCH-Naph)s represent an attractive polymechanophore system explore multifaceted response solution solid states, owing synthetic scalability, functional diversity, efficient polymerization, facile mechanoactivation.