Regioisomer-Specific Mechanochromism of Naphthopyran in Polymeric Materials,Journal of the American Chemical Society

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Regioisomer-Specific Mechanochromism of Naphthopyran in Polymeric Materials
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2016-09-12 , DOI: 10.1021/jacs.6b07610
Maxwell J. Robb ₁ , Tae Ann Kim ₁ , Abigail J. Halmes ₁ , Scott R. White ₁ , Nancy R. Sottos ₁ , Jeffrey S. Moore ₁

Affiliation

Transformation of naphthopyran into a colored merocyanine species in polymeric materials is achieved using mechanical force. We demonstrate that the mechanochemical reactivity of naphthopyran is critically dependent on the regiochemistry, with only one particular substitution pattern leading to successful mechanochemical activation. Two alternative regioisomers with different polymer attachment points are demonstrated to be mechanochemically inactive. This trend in reactivity is accurately predicted by DFT calculations, reinforcing predictive capabilities in mechanochemical systems. We rationalize the reactivity differences between naphthopyran regioisomers in terms of the alignment of the target C-O pyran bond with the direction of the applied mechanical force and its effect on mechanochemical transduction along the reaction coordinate.

中文翻译：

高分子材料中萘并吡喃的区域异构体特异性机械变色

使用机械力将萘并吡喃转化为聚合物材料中的有色部花青物质。我们证明萘并吡喃的机械化学反应性严重依赖于区域化学，只有一种特定的取代模式导致成功的机械化学活化。具有不同聚合物连接点的两种替代区域异构体被证明是机械化学惰性的。这种反应性趋势可以通过 DFT 计算准确预测，增强了机械化学系统的预测能力。我们根据目标 CO 吡喃键与施加的机械力方向的排列及其对沿反应坐标的机械化学转导的影响来合理化萘并吡喃区域异构体之间的反应性差异。

更新日期：2016-09-12

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