Electrochemically Active Crosslinking Reaction for Fluorescent Labeling of Aliphatic Alkenes
Electrochemically Active Crosslinking Reaction for Fluorescent Labeling of Aliphatic Alkenes
复制标题
用于脂肪族烯烃荧光标记的电化学活性交联反应
DOI：
10.1002/chem.201103630
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发表时间：
2012
影响因子：
4.3
通讯作者：
Kazuhiro Chiba
中科院分区：
文献类型：
--
作者：
Shokaku Kim;Kumi Hirose;Jumpei Uematsu;Yuzuru Mikami;Kazuhiro Chiba
虽然交联反应是整合两种或多种功能或性质的有价值的工具，但由于传质困难，电化学合成在交联反应中的应用受到限制。因此，本研究的主要目的是探索电化学交联系统来构建荧光探针，由共价键的形成触发。第二个目的是将探针应用于不溶性目标。为了实现这些目标，电化学活性苯酚衍生物和脂肪族烯烃的组合被用来形成多环化合物。通过[3+2]环化反应生成的几种二氢苯并呋喃衍生物表现出荧光。此外，这种方法允许用电化学活性物质对烯烃修饰的硅胶进行有效修饰，这使得构建由C - C键形成触发的荧光探针成为可能。
Although cross‐linking reactions serve as a valuable tool for the integration of two or more functionalities or properties, the application of electrochemical synthesis to cross‐linking reactions is restricted due to the difficulty of mass transfer. Thus, the primary purpose of this research is to explore electrochemical cross‐linking systems to construct a fluorescent probe, triggered by the formation of a covalent linkage. The second purpose is to apply the probe to insoluble targets. Towards these goals, a combination of electrochemically active phenol derivatives and aliphatic alkenes were employed to form polycyclic compounds. Several of the dihydrobenzofuran derivatives formed through [3+2] cyclization reactions exhibited fluorescence. Furthermore, this approach allowed the effective modification of alkene‐modified silica gel with electrochemically active species, which enables the construction of fluorescent probes that are triggered by CC bond formation.