Expedient Synthesis of Heterobifunctional Triarylmethane Stoppers for Macromolecular Rotaxanes.,The Journal of Organic Chemistry

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Expedient Synthesis of Heterobifunctional Triarylmethane Stoppers for Macromolecular Rotaxanes.
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2020-01-23 , DOI: 10.1021/acs.joc.9b03063
Min Zhang ₁ , Olga Shvetsova ₁ , Guillaume De Bo ₁

Affiliation

Increasingly complex rotaxane-based molecular devices are interfaced with polymers and surfaces, but suitable bifunctional stoppering groups are lacking. Here, we report a two-step, high-yielding synthesis toward a new class of heterobifunctional triarylmethane stoppers. They possess hydroxyl and ester groups for further functionalization as well as halogen substituents conferring a diagnostic spectroscopic signature. Their utility was demonstrated with the synthesis of a chain-centered macromolecular rotaxane. This new stopper architecture should prove useful to connect rotaxanes with polymers and surfaces for applications in polymer mechanochemistry, single-molecule force spectroscopy, smart materials, and molecular machines.

中文翻译：

用于大分子轮烷的杂双功能三芳基甲烷塞子的简便合成方法。

越来越复杂的基于轮烷的分子装置与聚合物和表面接触，但是缺乏合适的双功能塞基。在这里，我们报告了针对新一类的异双功能三芳基甲烷塞子的两步，高产率合成。它们具有用于进一步官能化的羟基和酯基以及赋予诊断光谱特征的卤素取代基。通过合成以链为中心的大分子轮烷证明了其实用性。这种新的塞子结构应该证明对将轮烷与聚合物和表面连接有用，可用于聚合物机械化学，单分子力谱，智能材料和分子机器中。

更新日期：2020-01-23

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