Formation of Functional Cyclooctadiene Derivatives by Supramolecularly‐ Controlled Topochemical Reactions and Their Use as Highly Selective Fluorescent Biomolecule Probes†,Chinese Journal of Chemistry

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Formation of Functional Cyclooctadiene Derivatives by Supramolecularly‐ Controlled Topochemical Reactions and Their Use as Highly Selective Fluorescent Biomolecule Probes†
Chinese Journal of Chemistry ( IF 5.5 ) Pub Date : 2020-04-14 , DOI: 10.1002/cjoc.202000125
Ming‐Ming Gan ₁ , Ying‐Feng Han _{1,

2}

Affiliation

Controlling the regio‐ and stereochemistry of the photoproducts in solution is far more challenging for polyenes than for monoalkenes. Herein, a supramolecularly‐controlled topochemical reaction of conjugated dienes in homogeneous system is developed, ultimately providing two cyclooctadiene‐cored tetraimidazolium molecular receptors exclusively. These cyclooctadiene derivatives exhibited highly sensitive and selective fluorescence sensing for thymine relative to other biologically relevant species in aqueous solution at physiological pH. Both the cyclooctadiene moieties and imidazolium units play important roles in the selective recognition observed. The presented supramolecularly‐controlled method allows the simple yet rare selective photoconversion of flexible cyclooctadiene derivatives in solution. This study offers a new synthetic strategy for the preparation of functional molecules with potential for use in biological applications.

中文翻译：

超分子控制的拓扑化学反应形成功能性环辛二烯衍生物并将其用作高选择性荧光生物分子探针†

对于多烯而言，控制溶液中光产物的区域和立体化学比单烯烃更具挑战性。本文研究了共轭二烯在均相系统中的超分子控制拓扑化学反应，最终仅提供了两个以环辛二烯为核心的四咪唑鎓分子受体。这些环辛二烯衍生物相对于生理pH水溶液中的其他生物学相关物种，对胸腺嘧啶表现出高度敏感和选择性的荧光传感。环辛二烯部分和咪唑鎓单元在观察到的选择性识别中均起重要作用。提出的超分子控制方法可以实现溶液中柔性环辛二烯衍生物的简单而罕见的选择性光转化。

更新日期：2020-04-14

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