Bicyclohexene-peri-naphthalenes: Scalable Synthesis, Diverse Functionalization, Efficient Polymerization, and Facile Mechanoactivation of Their Polymers,Journal of the American Chemical Society

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Bicyclohexene-peri-naphthalenes: Scalable Synthesis, Diverse Functionalization, Efficient Polymerization, and Facile Mechanoactivation of Their Polymers
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2020-07-30 , DOI: 10.1021/jacs.0c06454
Jinghui Yang ₁ , Matias Horst ₁ , Sabrina H Werby ₁ , Lynette Cegelski ₁ , Noah Z Burns ₁ , Yan Xia ₁

Affiliation

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

中文翻译：

双环己烯-环萘：其聚合物的可扩展合成、多样化功能化、高效聚合和简便的机械活化

为了寻求在压力下可以从非共轭状态转变为共轭状态以显着改变其性质的聚合物，我们开发了新一代梯型机械团单体，双环[2.2.0]己-5-烯-萘（ BCH-Naph)，可以直接有效地聚合。BCH-Naphs 可以使用现成的化学品以多克的量合成，并用各种富电子和缺电子取代基进行功能化，从而可以调整机械生成的共轭聚合物的光电和物理特性。BCH-Naph 的高效 ROMP 产生了具有受控 MW 和低分散性的超高分子量多机械载体。所得的聚 (BCH-Naph) 可以通过超声处理、研磨、甚至稀释溶液的简单搅拌，都会导致吸收和荧光的变化。由于合成的可扩展性、功能多样性、有效聚合和容易的机械活化，Poly(BCH-Naph)s 代表了一种有吸引力的多机械载体系统，用于探索溶液和固态下的多方面机械响应。

更新日期：2020-07-30

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