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
1. [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. doi: 10.1038/nmeth.4034
2. [2]
  Zhao, F.; Chen, Z.; Fan, C. B.; Liu, G.; Pu, S. Z. Dyes Pigm. 2019, 164, 390. doi: 10.1016/j.dyepig.2019.01.057
3. [3]
  Yin, Y.; Zhao, F.; Chen, Z.; Liu, G.; Pu, S. Z. Tetrahedron Lett. 2018, 59, 4416. doi: 10.1016/j.tetlet.2018.10.073
4. [4]
  Tang, A. L.; Chen, Z.; Liu, G.; Pu, S. Z. Tetrahedron Lett. 2018, 59, 3600. doi: 10.1016/j.tetlet.2018.08.040
5. [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).
6. [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).
7. [7]
  Li, Y. J.; Zhang, N.; Liu, J. H.; Jin, K.; Wang, S. Y. Chin. J. Org. Chem. 2018, 38, 3026(in Chinese).
8. [8]
  Heim, R. Nature 1995, 373, 663.
9. [9]
  Dean, K. M.; Palmer, A. E. Nat. Chem. Biol. 2014, 10, 512. doi: 10.1038/nchembio.1556
10. [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. doi: 10.1039/C8SC00130H
11. [11]
  Eggeling, C.; Willig, K. I.; Sahl, S. J.; Hell, S. W. Q. Rev. Biophys. 2015, 48, 178. doi: 10.1017/S0033583514000146
12. [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. doi: 10.1126/science.1127344
13. [13]
  Irie, M. Chem. Rev. 2000, 100, 1685. doi: 10.1021/cr980069d
14. [14]
  Fukaminato, T. J. Photochem. Photobiol. C 2011, 12, 177. doi: 10.1016/j.jphotochemrev.2011.08.006
15. [15]
  Chen, S.; Chen, L. J.; Yang, H. B.; Tian, H.; Zhu, W. J. Am. Chem. Soc. 2012, 134, 13596. doi: 10.1021/ja306748k
16. [16]
  Pu, S. Z.; Sun, Q.; Fan, C. B.; Wang, R. J.; Liu, G. J. Mater. Chem. C. 2016, 4, 3075. doi: 10.1039/C6TC00110F
17. [17]
  Cui, S. Q.; Qiu, S. Y.; Lu, R. M.; Pu, S. Z. Tetrahedron Lett. 2018, 59, 3365. doi: 10.1016/j.tetlet.2018.07.057
18. [18]
  Yun, C.; You, J.; Kim, J.; Huh, J.; Kim, E. J. Photochem. Photobiol. C 2009, 10, 111. doi: 10.1016/j.jphotochemrev.2009.05.002
19. [19]
  Park, H.; Jin, Y. J.; Kwak, G. Dyes Pigm. 2017, 146, 398. doi: 10.1016/j.dyepig.2017.07.039
20. [20]
  Ritchie, C.; Vamvounis, G.; Soleimaninejad, H.; Smith, T. A.; Bieske, E. J.; Dryza, V. Phys. Chem. Chem. Phys. 2017, 19, 19984. doi: 10.1039/C7CP02818K
21. [21]
  Uno, K.; Niikura, H.; Morimoto, M.; Ishibashi, Y.; Miyasaka, H.; Irie, M. J. Am. Chem. Soc. 2011, 133, 13558. doi: 10.1021/ja204583e
22. [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. doi: 10.1021/jacs.7b00274
23. [23]
  Takagi, Y.; Morimoto, M.; Kashihara, R.; Fujinami, S.; Ito, S.; Miyasaka, H.; Irie, M. Tetrahedron 2017, 73, 4918. doi: 10.1016/j.tet.2017.03.040
24. [24]
  Irie, M.; Mohri, M. J. Org. Chem. 1988, 53, 808. doi: 10.1021/jo00239a023
25. [25]
  Deng, X.; Liebeskind, L. S. J. Am. Chem. Soc. 2001, 123, 7703. doi: 10.1021/ja0106220
26. [26]
  Yamaguchi, T.; Irie, M. J. Mater. Chem. 2006, 16, 4690. doi: 10.1039/b611294c
27. [27]
  Sysoiev, D.; Yushchenko, T.; Scheer, E.; Groth, U.; Steiner, U. E.; Exner, T. E.; Huhn, T. Chem. Commun. 2012, 48, 11355. doi: 10.1039/c2cc35726g
28. [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. doi: 10.1002/chem.201003716
29. [29]
  Wolf, J.; Eberspächer, I.; Groth, U.; Huth, T. J. Org. Chem. 2013, 78, 8366. doi: 10.1021/jo401065b
30. [30]
  Gidron, O.; Diskin-Posner, Y.; Bendikov, M. J. Am. Chem. Soc. 2010, 132, 2148. doi: 10.1021/ja9093346
31. [31]
  Gidron, O.; Dadvand, A.; Sheynin, Y.; Bendikov, M.; Perepichka, D. F. Chem. Commun. 2011, 47, 1976. doi: 10.1039/C0CC04699J
32. [32]
  Gidron, O.; Bendikov, M. Angew. Chem., Int. Ed. 2014, 53, 2546. doi: 10.1002/anie.201308216
33. [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. doi: 10.1002/advs.201700005
34. [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. [35]
  Gidron, O.; Varsano, N.; Shimon, L. J. W.; Leitus, G.; Bendikov, M. Chem. Commun. 2013, 49, 6256. doi: 10.1039/c3cc41795f
36. [36]
  Binder, J. B.; Raines, R. T. J. Am. Chem. Soc. 2009, 131, 1979. doi: 10.1021/ja808537j
37. [37]
  Wang, S.; Zhou, Y.; Zhu, L.; Zhang, J.; Zou, Q.; Zeng, T.; Chen, W. Chem. Commun. 2017, 53, 9570. doi: 10.1039/C7CC05773C
38. [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. [39]
  Li, W.; Jiao, C.; Li, X.; Xie, K.; Nakatani, K.; Tian, H.; Zhu, W. Angew. Chem., Int. Ed. 2014, 53, 4603. doi: 10.1002/anie.201310438
40. [40]
  Pati, P. B.; Zade, S. S. RSC Adv. 2013, 3, 13457. doi: 10.1039/c3ra41413b
41. [41]
  Zhou, X.; Lv, X.; Hao, J.; Liu, D.; Guo, W. Dyes Pigm. 2012, 95, 168. doi: 10.1016/j.dyepig.2012.03.025
42. [42]
  Lee, C. H.; Yoon, H. J.; Shim, J. S.; Jiang, W. D. Chem.-Eur. J. 2012, 18, 4513. doi: 10.1002/chem.201200008
43. [43]
  Yang, L.; Li, X.; Yang, J.; Qu, Y.; Hua, J. ACS Appl. Mater. Interfaces 2013, 5, 1317. doi: 10.1021/am303152w
44. [44]
  Zou, Q.; Li, X.; Xu, Q.; Ågren, H.; Zhao, W.; Qu, Y. RSC Adv. 2014, 4, 59809. doi: 10.1039/C4RA11567H
1. [1]
  Chuanfeng Fan , Jian Gao , Yingkai Gao , Xintong Yang , Gaoning Li , Xiaochun Wang , Fei Li , Jin Zhou , Haifeng Yu , Yi Huang , Jin Chen , Yingying Shan , Li Chen . A non-peptide-based chymotrypsin-targeted long-wavelength emission fluorescent probe with large Stokes shift and its application in bioimaging. Chinese Chemical Letters, 2024, 35(10): 109838-. doi: 10.1016/j.cclet.2024.109838
2. [2]
  Xing Tian , Di Wu , Wanheng Wei , Guifu Dai , Zhanxian Li , Benhua Wang , Mingming Yu . A lipid droplets-targetable fluorescent probe for polarity detection in cells of iron death, inflammation and fatty liver tissue. Chinese Chemical Letters, 2024, 35(6): 108912-. doi: 10.1016/j.cclet.2023.108912
3. [3]
  Yijian Zhao , Jvzhe Li , Yunyi Shi , Jie Hu , Meiyi Liu , Yao Shen , Xinglin Hou , Qiuyue Wang , Qi Wang , Zhiyi Yao . A label-free and ratiometric fluorescent sensor based on porphyrin-metal-organic frameworks for sensitive detection of ochratoxin A in cereal. Chinese Chemical Letters, 2025, 36(4): 110132-. doi: 10.1016/j.cclet.2024.110132
4. [4]
  Ying Wang , Hong Yang , Caixia Zhu , Qing Hong , Xuwen Cao , Kaiyuan Wang , Yuan Xu , Yanfei Shen , Songqin Liu , Yuanjian Zhang . Cascading oxidoreductases-like nanozymes for high selective and sensitive fluorescent detection of ascorbic acid. Chinese Chemical Letters, 2025, 36(4): 110153-. doi: 10.1016/j.cclet.2024.110153
5. [5]
  Wei-Tao Dou , Qing-Wen Zeng , Yan Kang , Haidong Jia , Yulian Niu , Jinglong Wang , Lin Xu . Construction and application of multicomponent fluorescent droplets. Chinese Chemical Letters, 2025, 36(1): 109995-. doi: 10.1016/j.cclet.2024.109995
6. [6]
  Wenyi Mei , Lijuan Xie , Xiaodong Zhang , Cunjian Shi , Fengzhi Wang , Qiqi Fu , Zhenjiang Zhao , Honglin Li , Yufang Xu , Zhuo Chen . Design, synthesis and biological evaluation of fluorescent derivatives of ursolic acid in living cells. Chinese Chemical Letters, 2024, 35(5): 108825-. doi: 10.1016/j.cclet.2023.108825
7. [7]
  Chuan-Zhi Ni , Ruo-Ming Li , Fang-Qi Zhang , Qu-Ao-Wei Li , Yuan-Yuan Zhu , Jie Zeng , Shuang-Xi Gu . A chiral fluorescent probe for molecular recognition of basic amino acids in solutions and cells. Chinese Chemical Letters, 2024, 35(10): 109862-. doi: 10.1016/j.cclet.2024.109862
8. [8]
  Ya-Ping Liu , Zhi-Rong Gui , Zhen-Wen Zhang , Sai-Kang Wang , Wei Lang , Yanzhu Liu , Qian-Yong Cao . A phenylphenthiazide anchored Tb(Ⅲ)-cyclen complex for fluorescent turn-on sensing of ClO⁻. Chinese Chemical Letters, 2025, 36(2): 109769-. doi: 10.1016/j.cclet.2024.109769
9. [9]
  Tao Liu , Xuwei Han , Xueyi Sun , Weijie Zhang , Ke Gao , Runan Min , Yuting Tian , Caixia Yin . An activated fluorescent probe to monitor NO fluctuation in Parkinson’s disease. Chinese Chemical Letters, 2025, 36(3): 110170-. doi: 10.1016/j.cclet.2024.110170
10. [10]
  Rui Wang , Yang Liang , Julius Rebek Jr. , Yang Yu . Stabilization and detection of labile reaction intermediates in supramolecular containers. Chinese Chemical Letters, 2024, 35(6): 109228-. doi: 10.1016/j.cclet.2023.109228
11. [11]
  Zihong Li , Jie Cheng , Ping Huang , Guoliang Wu , Weiying Lin . Activatable photoacoustic bioprobe for visual detection of aging in vivo. Chinese Chemical Letters, 2024, 35(4): 109153-. doi: 10.1016/j.cclet.2023.109153
12. [12]
  Tiankai Sun , Hui Min , Zongsu Han , Liang Wang , Peng Cheng , Wei Shi . Rapid detection of nanoplastic particles by a luminescent Tb-based coordination polymer. Chinese Chemical Letters, 2024, 35(5): 108718-. doi: 10.1016/j.cclet.2023.108718
13. [13]
  Yuxin Xiao , Xiaowei Wang , Yutong Yin , Fangchao Yin , Jinchao Li , Zhiyuan Hou , Mashooq Khan , Rusong Zhao , Wenli Wu , Qiongzheng Hu . Distance-based lateral flow biosensor for the quantitative detection of bacterial endotoxin. Chinese Chemical Letters, 2024, 35(12): 109718-. doi: 10.1016/j.cclet.2024.109718
14. [14]
  Haibo Wan , Zhengzhong Lv , Jicai Jiang , Xuefeng Cheng , Qingfeng Xu , Haibin Shi , Jianmei Lu . Multidimensional detection of roxarsone via AIE-based sulfates. Chinese Chemical Letters, 2025, 36(3): 110023-. doi: 10.1016/j.cclet.2024.110023
15. [15]
  Linfang Wang , Jing Liu , Minghao Ren , Wei Guo . A highly sensitive fluorescent HClO probe for discrimination between cancerous and normal cells/tissues. Chinese Chemical Letters, 2024, 35(6): 108945-. doi: 10.1016/j.cclet.2023.108945
16. [16]
  Liangji Chen , Zhen Yuan , Fudong Feng , Xin Zhou , Zhile Xiong , Wuji Wei , Hao Zhang , Banglin Chen , Shengchang Xiang , Zhangjing Zhang . A hydrogen-bonded organic framework containing fluorescent carbazole and responsive pyridyl units for sensing organic acids. Chinese Chemical Letters, 2024, 35(9): 109344-. doi: 10.1016/j.cclet.2023.109344
17. [17]
  Yang Liu , Leilei Zhang , Kaixuan Liu , Ling-Ling Wu , Hai-Yu Hu . Penicillin G acylase-responsive near-infrared fluorescent probe: Unravelling biofilm regulation and combating bacterial infections. Chinese Chemical Letters, 2024, 35(11): 109759-. doi: 10.1016/j.cclet.2024.109759
18. [18]
  Huamei Zhang , Jingjing Liu , Mingyue Li , Shida Ma , Xucong Zhou , Aixia Meng , Weina Han , Jin Zhou . Imaging polarity changes in pneumonia and lung cancer using a lipid droplet-targeted near-infrared fluorescent probe. Chinese Chemical Letters, 2024, 35(12): 110020-. doi: 10.1016/j.cclet.2024.110020
19. [19]
  Beitong Zhu , Xiaorui Yang , Lirong Jiang , Tianhong Chen , Shuangfei Wang , Lintao Zeng . A portable and versatile fluorescent platform for high-throughput screening of toxic phosgene, diethyl chlorophosphate and volatile acyl chlorides. Chinese Chemical Letters, 2025, 36(1): 110222-. doi: 10.1016/j.cclet.2024.110222
20. [20]
  Pei Huang , Weijie Zhang , Junping Wang , Fangjun Huo , Caixia Yin . Rapid and specific fluorescent probe visualizes dynamic correlation of Cys and HClO in OGD/R. Chinese Chemical Letters, 2025, 36(1): 109778-. doi: 10.1016/j.cclet.2024.109778

Get Citation

PDF

XML

Metrics

PDF Downloads(6)
Abstract views(1455)
HTML views(85)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142