有机化学 ›› 2019, Vol. 39 ›› Issue (9): 2492-2498.DOI: 10.6023/cjoc201903033 上一篇    下一篇

研究论文

一种新型二氰基乙烯修饰的二呋喃环戊烯光开关:荧光性质、传感性能和生物应用

郑天骄a, 陈炫颖a, 朱亮亮c, 王道累a, 邹祺a, 曾涛b, 陈文博a   

  1. a 上海电力大学 上海市电力材料防护与新材料重点实验室 上海 200090;
    b 上海市材料研究所 上海市工程材料应用与评价重点实验室 上海 200437;
    c 复旦大学高分子科学系 聚合物分子工程国家重点实验室 上海 200438
  • 收稿日期:2019-03-17 修回日期:2019-04-22 出版日期:2019-09-25 发布日期:2019-05-06
  • 通讯作者: 邹祺, 曾涛, 陈文博 E-mail:qzou@shiep.edu.cn;zengtao0626@126.com;wenbochen@shiep.edu.cn
  • 基金资助:

    国家自然科学基金(Nos.21406137,61502297)、上海市自然科学基金(No.17ZR1447100)和上海市科学技术委员会(No.14DZ2261000)资助项目.

A New Dicyano-vinyl Modified Difurylperhydrocyclopentene Photoswitch: Fluorescent Properties, Sensing Ability and in vivo Application

Zheng Tianjiaoa, Chen Xuanyinga, Zhu Liangliangc, Wang Daoleia, Zou Qia, Zeng Taob, Chen Wenboa   

  1. a Shanghai Key Laboratory of Materials Protection and Advanced Materials in Electric Power, Shanghai University of Electric Power, Shanghai 200090;
    b Shanghai Key Laboratory of Engineering Materials Application and Evaluation, Shanghai Research Institute of Materials, Shanghai 200437;
    c State Key Laboratory of Molecular Engineering of Polymers, Department of Macromolecular Science, Fudan University, Shanghai 200438
  • Received:2019-03-17 Revised:2019-04-22 Online:2019-09-25 Published:2019-05-06
  • Contact: 10.6023/cjoc201903033 E-mail:qzou@shiep.edu.cn;zengtao0626@126.com;wenbochen@shiep.edu.cn
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21406137, 61502297), the Natural Science Foundation of Shanghai City (No. 17ZR1447100), and the Science and Technology Commission of Shanghai Municipality (No. 14DZ2261000).

近年来,借助于高度优化的小分子荧光染料,荧光蛋白和先进的标记技术,荧光标记技术得到了极大的发展.二芳基乙烯光开关荧光染料的研究,主要通过在二芳基乙烯中引入荧光核和对芳基的结构修饰.与噻吩相比,呋喃具有更好的刚性、溶解性和可生物降解能力以及更强的荧光.因此,二呋喃乙烯可以作为荧光标记技术的小分子荧光染料.设计并制备了一种基于二氰基乙烯的二呋喃乙烯新型荧光光开关.该化合物在溶液中呈现典型的可逆光致变色性能,且以其出色的选择性、灵敏度和高对比度来实现氰根离子的荧光检测.此外,通过核磁滴定实验,解释了其对氰根离子的响应机理.由于采用呋喃替换噻吩使得该化合物拥有更强的荧光,成功应用于生物体内的荧光染料和氰根离子探针.

关键词: 二呋喃乙烯, 光开关, 荧光检测, 氰化物, 生物成像

Recently, fluorescent labeling techniques have been greatly developed with the aid of highly optimized small-molecule fluorescent dyes, fluorescent proteins and advanced tagging techniques. Many reasonable strategies have been used to design fluorescent diarylethene, mainly focusing on the introduction of luminophores by conjugated junction and the modification of aryl cores in the diarylethene. Compared to thiophene, furan has superior properties such as solubility, biodegradable ability and rigidity fluorescence. Therefore, difurylethene is a better candidate for fluorescent labeling techniques. Herein, a new fluorescent photoswitch based on dicyano-vinyl modified difurylethenes was designed and prepared. This compound demonstrates typical reversible photochromism in solution and outstanding performance for the fluorescent detection of cyanide ions with excellent selectivity, sensitivity and high contrast. Furthermore, the mechanism of sensing toward cyanide ions was explained by 1H NMR titrations experiments. Owing to the strong fluorescence from a superior derivation with furan instead of thiophene, it is successfully applied as the fluorescent dyes and probe for detecting cyanide ions in vivo application.

Key words: difurylperhydrocyclopentene, photoswitch, fluorescent detection, cyanide, bioimaging