Bicyclo[3.2.0]heptane Mechanophores for the Non-scissile and Photochemically Reversible Generation of Reactive Bis-enones,Journal of the American Chemical Society

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Bicyclo[3.2.0]heptane Mechanophores for the Non-scissile and Photochemically Reversible Generation of Reactive Bis-enones
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2012-07-25 , DOI: 10.1021/ja3063666
Zachary S Kean ₁ , Ashley L Black Ramirez , Yufan Yan , Stephen L Craig

Affiliation

Force-induced transformations of polymer-bound functionalities have the potential to produce a rich array of stress-responsive behavior. One area of particular interest is the activation of non-scissile mechanophores in which latent reactivity can be unveiled that, under the appropriate conditions, could lead to constructive bond formation in materials exposed to typically destructive stress. Here, the mechanical activation of a bicyclo[3.2.0]heptane (BCH) mechanophore is demonstrated via selective labeling of bis-enone products. BCH ring-opening produces large local elongation (>4 Å) and products that are reactive to conjugate additions under mild conditions. Subsequent photocyclization regenerates the initial BCH functionality, providing switchable structure and reactivity along the polymer backbone in response to stress and visible light.

中文翻译：

双环[3.2.0]庚烷机械载体用于非裂解和光化学可逆生成反应性双烯酮

力诱导的聚合物结合功能的转变有可能产生丰富的应力响应行为。特别令人感兴趣的一个领域是非裂变机械载体的激活，其中可以揭示潜在的反应性，在适当的条件下，可以导致暴露于典型破坏性应力的材料中形成建设性的键。在这里，通过双烯酮产物的选择性标记证明了双环[3.2.0]庚烷（BCH）机械载体的机械活化。 BCH 开环产生较大的局部伸长率 (>4 Å) 和在温和条件下对缀合物加成反应的产物。随后的光环化作用会再生最初的 BCH 功能，沿着聚合物主链提供可切换的结构和反应性，以响应压力和可见光。

更新日期：2012-07-25

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