Citation: Zheng Tianjiao, Chen Xuanying, Zhu Liangliang, Wang Daolei, Zou Qi, Zeng Tao, Chen Wenbo. A New Dicyano-vinyl Modified Difurylperhydrocyclopentene Photoswitch: Fluorescent Properties, Sensing Ability and in vivo Application[J]. Chinese Journal of Organic Chemistry, ;2019, 39(9): 2492-2498. doi: 10.6023/cjoc201903033 shu

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

Zheng Tianjiao ^a ,
Chen Xuanying ^a ,
Zhu Liangliang ^c ,
Wang Daolei ^a ,
Zou Qi ^a,, ,
Zeng Tao ^b,, ,
Chen Wenbo ^a,,

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

Corresponding author: Zou Qi, qzou@shiep.edu.cn Zeng Tao, zengtao0626@126.com Chen Wenbo, wenbochen@shiep.edu.cn
Received Date: 17 March 2019
Revised Date: 22 April 2019
Available Online: 6 September 2019
Fund Project: the National Natural Science Foundation of China 61502297the National Natural Science Foundation of China 21406137Project 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)the Natural Science Foundation of Shanghai City 17ZR1447100the Science and Technology Commission of Shanghai Municipality 14DZ2261000

Figures(9)

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.
- difurylperhydrocyclopentene,
- photoswitch,
- fluorescent detection,
- cyanide,
- bioimaging
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