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A Strategy for the Detection of Diels-Alder Reactions Using Fluorescence Quenching of Conjugated Polymers

机译：用共轭聚合物荧光猝灭检测狄尔斯-阿尔德反应的策略

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摘要

A new method has been developed to detect the formation of carbon-carbon bonds by Diels-Alder reactions based on the fluorescence quenching of conjugated polymers. Conjugated copolymers containing various amounts of functional furan pendant groups (PFP-F) have been synthesized and characterized. A maleimide group linked to l-methyl-4,4-bipyridinium iodide acts as the electron quencher (M-MV~(2+)). The Diels-Alder reaction between the maleimide and furan moieties results in intramolecular electron transfer from the conjugated copolymer to the MV~(2+), and thus the fluorescence of the conjugated copoly-mer is quenched via a photoinduced electron transfer process. Higher furan concentrations increase the fluorescence quenching efficiency (EF) of the conjugated copolymers. The copolymer PFP-F_3 with the highest furan content can be used as a platform to monitor Diels-Alder reactions. The PFP-F_3/M-MV~(2+)system can also be used to screen catalysts for Diels-Alder reactions.
机译：已经开发了一种新方法，用于基于共轭聚合物的荧光猝灭检测通过Diels-Alder反应形成的碳-碳键。合成和表征了含有各种功能呋喃侧基的共轭共聚物（PFP-F）。与1-甲基-4,4-碘联吡啶鎓连接的马来酰亚胺基团用作电子猝灭剂（M-MV〜（2+））。马来酰亚胺和呋喃部分之间的狄尔斯-阿尔德反应导致分子内电子从共轭共聚物转移至MV_（2+），因此共轭共聚物的荧光通过光致电子转移过程被猝灭。较高的呋喃浓度可提高共轭共聚物的荧光猝灭效率（EF）。呋喃含量最高的共聚物PFP-F_3可用作监测Diels-Alder反应的平台。 PFP-F_3 / M-MV〜（2+）系统也可用于筛选Diels-Alder反应的催化剂。

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