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

doi:10.6023/cjoc201903033

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (9): 2492-2498.DOI: 10.6023/cjoc201903033 Previous Articles Next Articles

Special Issue: 荧光探针-生物传感合辑

ARTICLE

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

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 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 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

Received:2019-03-17 Revised:2019-04-22 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).

1. A New Dicyano-vinyl Modified Difurylperhydrocyclopentene Photoswitch: Fluorescent Properties, Sensing Ability and in vivo Application.PDF(749KB)

Abstract

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

Cite this article

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]. Chin. J. Org. Chem., 2019, 39(9): 2492-2498.

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[1] Grimm, J. B.; English, B. P.; Choi, H.; Muthusamy, A. K.; Mehl, B. P.; Dong, P.; Brown, T. A.; Lippincott-Schwartz, J.; Liu, Z.; Lionnet, T.; Lavis, L. D. Nat. Methods 2016, 13, 985.
[2] Zhao, F.; Chen, Z.; Fan, C. B.; Liu, G.; Pu, S. Z. Dyes Pigm. 2019, 164, 390.
[3] Yin, Y.; Zhao, F.; Chen, Z.; Liu, G.; Pu, S. Z. Tetrahedron Lett. 2018, 59, 4416.
[4] Tang, A. L.; Chen, Z.; Liu, G.; Pu, S. Z. Tetrahedron Lett. 2018, 59, 3600.
[5] Ju, Z. Y.; Shu, P. H.; Xie, Z. Y.; Jiang, Y. Q.; Tao, W. J.; Xu, Z. H. Chin. J. Org. Chem. 2019, 39, 697(in Chinese). (鞠志宇, 舒朋华, 谢智宇, 蒋雨晴, 陶伟杰, 许志红, 有机化学, 2019, 39, 697.)
[6] Jiao, C. P.; Liu, Y. Y.; Lu, W. J.; Zhang, P. P.; Wang, Y. F. Chin. J. Org. Chem. 2019, 39, 591(in Chinese). (矫春鹏, 刘媛媛, 路文娟, 张平平, 王延风, 有机化学, 2019, 39, 591.)
[7] Li, Y. J.; Zhang, N.; Liu, J. H.; Jin, K.; Wang, S. Y. Chin. J. Org. Chem. 2018, 38, 3026(in Chinese). (李英俊, 张楠, 刘季红, 靳焜, 王思远, 有机化学, 2018, 38, 3026.)
[8] Heim, R. Nature 1995, 373, 663.
[9] Dean, K. M.; Palmer, A. E. Nat. Chem. Biol. 2014, 10, 512.
[10] Xiong, Y.; Jentzsch, A. V.; Osterrieth, J. W. M.; Sezgin, E.; Sazanovich, I. V.; Reqlinski, K.; Galiani, S.; Parker, A. W.; Eggeling, C.; Anderson, H. L. Chem. Sci. 2018, 9, 3029.
[11] Eggeling, C.; Willig, K. I.; Sahl, S. J.; Hell, S. W. Q. Rev. Biophys. 2015, 48, 178.
[12] Betzig, E.; Patterson, G. H.; Sougrat, R.; Lindwasser, O. W.; Olenych, S.; Bonifacino, J. S.; Davidson, M. W.; Lippincott-Schwartz, J.; Hess, H. F. Science 2006, 313, 1642.
[13] Irie, M. Chem. Rev. 2000, 100, 1685.
[14] Fukaminato, T. J. Photochem. Photobiol. C 2011, 12, 177.
[15] Chen, S.; Chen, L. J.; Yang, H. B.; Tian, H.; Zhu, W. J. Am. Chem. Soc. 2012, 134, 13596.
[16] Pu, S. Z.; Sun, Q.; Fan, C. B.; Wang, R. J.; Liu, G. J. Mater. Chem. C. 2016, 4, 3075.
[17] Cui, S. Q.; Qiu, S. Y.; Lu, R. M.; Pu, S. Z. Tetrahedron Lett. 2018, 59, 3365.
[18] Yun, C.; You, J.; Kim, J.; Huh, J.; Kim, E. J. Photochem. Photobiol. C 2009, 10, 111.
[19] Park, H.; Jin, Y. J.; Kwak, G. Dyes Pigm. 2017, 146, 398.
[20] Ritchie, C.; Vamvounis, G.; Soleimaninejad, H.; Smith, T. A.; Bieske, E. J.; Dryza, V. Phys. Chem. Chem. Phys. 2017, 19, 19984.
[21] Uno, K.; Niikura, H.; Morimoto, M.; Ishibashi, Y.; Miyasaka, H.; Irie, M. J. Am. Chem. Soc. 2011, 133, 13558.
[22] Roubinet, B.; Weber, M.; Shojaei, H.; Bates, M.; Bossi, M. L.; Belov, V. N.; Irie, M.; Hell, S. W. J. Am. Chem. Soc. 2017, 139, 6611.
[23] Takagi, Y.; Morimoto, M.; Kashihara, R.; Fujinami, S.; Ito, S.; Miyasaka, H.; Irie, M. Tetrahedron 2017, 73, 4918.
[24] Irie, M.; Mohri, M. J. Org. Chem. 1988, 53, 808.
[25] Deng, X.; Liebeskind, L. S. J. Am. Chem. Soc. 2001, 123, 7703.
[26] Yamaguchi, T.; Irie, M. J. Mater. Chem. 2006, 16, 4690.
[27] Sysoiev, D.; Yushchenko, T.; Scheer, E.; Groth, U.; Steiner, U. E.; Exner, T. E.; Huhn, T. Chem. Commun. 2012, 48, 11355.
[28] Sysoiev, D.; Fedoseev, A.; Kim, Y.; Boneberg, J.; Huhn, T.; Leiderer, P.; Scheer, E.; Groth, U.; Steiner, U. E. Chem.-Eur. J. 2011, 17, 6663.
[29] Wolf, J.; Eberspächer, I.; Groth, U.; Huth, T. J. Org. Chem. 2013, 78, 8366.
[30] Gidron, O.; Diskin-Posner, Y.; Bendikov, M. J. Am. Chem. Soc. 2010, 132, 2148.
[31] Gidron, O.; Dadvand, A.; Sheynin, Y.; Bendikov, M.; Perepichka, D. F. Chem. Commun. 2011, 47, 1976.
[32] Gidron, O.; Bendikov, M. Angew. Chem., Int. Ed. 2014, 53, 2546.
[33] Zhao, Z.; Nie, H.; Ge, C.; Cai, Y.; Xiong, Y.; Qi, J.; Wu, W.; Kwok, R. T. K.; Gao, X.; Qin, A.; Lam, J. W. Y.; Tang, B. Z. Adv. Sci. 2017, 4, 1700005.
[34] Gidron, O.; Dadvand, A.; Sun, E. W. H.; Chung, I.; Shimon, L. J. W.; Bendikov, M.; Perepichka, D. F. J. Mater. Chem. C 2013, 1, 4358.
[35] Gidron, O.; Varsano, N.; Shimon, L. J. W.; Leitus, G.; Bendikov, M. Chem. Commun. 2013, 49, 6256.
[36] Binder, J. B.; Raines, R. T. J. Am. Chem. Soc. 2009, 131, 1979.
[37] Wang, S.; Zhou, Y.; Zhu, L.; Zhang, J.; Zou, Q.; Zeng, T.; Chen, W. Chem. Commun. 2017, 53, 9570.
[38] Lucas, L. N.; Jong, J. J. D.; Esch, J. H.; Esch, J. H.; Kellogg, R. M.; Feringa, B. L. Eur. J. Org. Chem. 2003, 155.
[39] Li, W.; Jiao, C.; Li, X.; Xie, K.; Nakatani, K.; Tian, H.; Zhu, W. Angew. Chem., Int. Ed. 2014, 53, 4603.
[40] Pati, P. B.; Zade, S. S. RSC Adv. 2013, 3, 13457.
[41] Zhou, X.; Lv, X.; Hao, J.; Liu, D.; Guo, W. Dyes Pigm. 2012, 95, 168.
[42] Lee, C. H.; Yoon, H. J.; Shim, J. S.; Jiang, W. D. Chem.-Eur. J. 2012, 18, 4513.
[43] Yang, L.; Li, X.; Yang, J.; Qu, Y.; Hua, J. ACS Appl. Mater. Interfaces 2013, 5, 1317.
[44] Zou, Q.; Li, X.; Xu, Q.; Ågren, H.; Zhao, W.; Qu, Y. RSC Adv. 2014, 4, 59809.

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

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

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