Synthesis and Recognition Properties of Fluoroborodipyrrole Fluorescent Probes Based on Fluorine Triggered Cascade Releasing

doi:10.6023/cjoc202007008

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (1): 303-309.DOI: 10.6023/cjoc202007008 Previous Articles Next Articles

Article

基于氟引发串联释放的氟硼二吡咯类荧光探针的合成及其识别性能

陈曦^a, 高晨^a, 付超^a, 朱婷婷^a, 刘振江^a^,^*(), 刘传祥^a^,^*()

a 上海应用技术大学化学与环境工程学院上海 201418

收稿日期:2020-07-02 修回日期:2020-08-12 发布日期:2020-10-12
通讯作者: 刘振江, 刘传祥
作者简介:
* Corresponding authors. E-mail: zjliu@sit.edu.cn; cxliu@sit.edu.cn
基金资助:
上海市自然科学基金(17ZR1429900); 上海市化学生物学重点实验室开放基金(); 上海“化学工程与技术(香料香精技术与工程)”高原学科和上海应用技术大学青年科技人才发展基金()

Synthesis and Recognition Properties of Fluoroborodipyrrole Fluorescent Probes Based on Fluorine Triggered Cascade Releasing

Xi Chen^a, Chen Gao^a, Chao Fu^a, Tingting Zhu^a, Zhenjiang Liu^a^,^*(), Chuanxiang Liu^a^,^*()

a School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418

Received:2020-07-02 Revised:2020-08-12 Published:2020-10-12
Contact: Zhenjiang Liu, Chuanxiang Liu
Supported by:
the Natural Science Foundation of Shanghai(17ZR1429900); the Opening Fund of Shanghai Key Laboratory of Chemical Biology(); the Opening Fund of Shanghai Key Laboratory of Chemical Biology, the Chemical Engineering and Technology (Perfume and Aroma Technology) of Shanghai Plateau Discipline and the Development Foundation of Young Scientific Talents of Shanghai Institute of Technology(ZQ2019-15)

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Abstract

4-Hydroxy-fluoroborodipyrrole is used as fluorophore, and tert-butyldiphenylsilyl (TBDPS) is used as protective group for active hydroxyl groups. A novel fluoroborodipyrrole type of fluoride ion fluorescent probeR based on fluorine ion causing cleavage of Si—O bond to trigger cascade releasing was designed and synthesized. Spectral experimental studies showed that after the interaction of the fluorescent probe and fluoride ion, a new absorption peak appeared at 605 nm in the ultraviolet absorption spectrum. The solution includingR changed from orange to blue, the maximum emission peak at 514 nm in the fluorescence emission spectrum decreased, and the fluorescence color changed from green to fluorescence quenching. In addition, the use of fluorescent probeR under the test paper conditions also enables the naked eye detection of fluoride ions.

Key words: fluoroborodipyrrole, fluorescent probe, fluoride ion, detection

Cite this article

Xi Chen, Chen Gao, Chao Fu, Tingting Zhu, Zhenjiang Liu, Chuanxiang Liu. Synthesis and Recognition Properties of Fluoroborodipyrrole Fluorescent Probes Based on Fluorine Triggered Cascade Releasing[J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 303-309.

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Fig. & Tab. 7

Scheme 1. Synthetic route of probe molecule R

Figure 1. (A) Absorption spectra responses ofR (20 μmol/L) inN,N-dimethylformamide (DMF) with various anions (Inset: the illustration of their corresponding naked-eye photo under natural light, from left to right:R only, F–, CN–, Cl–, Br–, I–, AcO–, $H_{2}PO_{4}^{-}$, $HSO_{4}^{-}$, $ClO_{4}^{-}$, $SCN^{-}$, $BF_{4}^{-}$, $NO_{3}^{-}$) and (B) UV absorption spectrum ofR (20 μmol/L) upon titration with TBAF (5 mmol/L) (0~3.4 equiv.) in different concentrations in DMF (Inset: plot of absorption changes at 495 and 608 nm versus TBAF)

Figure 2. (A) Fluorescent emission spectra ofR (20 μmol/L) inN,N-dimethylformamide with various anions [Inset: the illustration shows its corresponding fluorescent picture under the UV light (365 nm), from left to right:R only, F–, CN–, Cl–, Br–, I–, AcO–,$H_{2}PO_4^{-}$, $HSO_4^{-}$, $ClO_{4}$, $SCN^{-}$, $BF_4^{-}$, $NO_{3}$] and (B) Fluorescent emission spectra ofR (20 μmol/L,λ ex=450 nm) with TBAF (0~7.8 equiv.) inN,N-dimethylformamide [Inset: the illustration shows the fluorescence intensity at 513 nm as a function of TBAF concentrations (λ ex=420 nm)]

Scheme 2. Mechanism of the interaction between probe R and fluoride ion

Figure 3. (a) UV absorption spectrum of probeR and referenceA2 before and after interaction with fluoride ion and (b) fluorescence emission spectrum of probeR and referenceA2 before and after interaction with fluoride ion

Figure 4. LC-MS of the mixture of probeR with fluoride ion

Figure 5. (A) The colour changes of theR-loaded test strips (1.0 mmol/L) after exposure to various concentrations of F– solution under natural light and (B) the fluorescence changes of theR-loaded test strips (1.0 mmol/L) with various concentrations of F– under UV light

References 29

[1]	Ghadiri M.R.; Granja J.R.; Buehler L.K. Nature 1994, 369, 301.
[2]	Huang G.B.; Chen Z.L.; Wei X. S.; Chen Y.; Li X.Y.; Zhong H.; Tan M.X. Chin. J. Org. Chem. 2020, 40, 614. (in Chinese)
	( 黄国保, 陈志林, 韦贤生, 陈钰, 李秀英, 仲辉, 谭明雄, 有机化学, 2020, 40, 614.).
[3]	Howe E.; Bhadbhade M.; Thordarson P. J. Am. Chem. Soc. 2014, 136, 7505.
[4]	Holloway J.M.; Dahlgren R.A.; Hansen B.; Casey W.H. Nature 1998, 295, 785.
[5]	Guha S.; Goodson F.; Roy S. J. Am. Chem. Soc. 2011, 133, 15256.
[6]	Beer P.D.; Hayes E.J. Coord. Chem. Rev. 2003, 240, 167.
[7]	Sessler J.L.; Gale P.A.; Cho W. S.J. Am. Chem. Soc. 2006, 128, 12281.
[8]	Sessler J.L.; Camiolo S.; Gale P.A. Coord. Chem. Rev. 2003, 240, 17.
[9]	Xu Z.; Chen X.Q.; Kim H.N.; Yoon J.Y. Chem. Soc. Rev. 2010, 39, 127.
[10]	Li Y.J.; Zhao Y.; Jin K.; Liu J.H.; Zhou X.X.; Yang K.D. Chin. J. Org. Chem. 2019, 39, 1013. (in Chinese)
	( 李英俊, 赵月, 靳焜, 刘季红, 周晓霞, 杨凯栋, 有机化学, 2019, 39, 1013.).
[11]	Chen K.; Han B.C.; Ji S.X.; Sun J.; Gao Z.Z.; Hou X.F. Acta Chim. Sinica 2019, 77, 365. (in Chinese)
	( 陈凯, 韩百川, 嵇思鑫, 孙瑾, 高振忠, 侯贤锋, 化学学报, 2019, 77, 365.).
[12]	Xu, Z ; Kim, S.K. ; Yoon, J. Chem. Soc. Rev. 2010, 39, 1457.
[13]	Li A.F.; Wang J.H.; Wang, F; Jiang, Y.B. Chem. Soc. Rev. 2010, 39, 3729.
[14]	Duke R.M.; Veale E.B.; Peffer F.M.; Krugerc P.E.; Gunn-laugsson, T. Chem. Soc. Rev. 2010, 39, 3936.
[15]	Cametti M.; Rissanen K. Chem. Commun. 2009, 2809.
[16]	Zhou J.P.; Wu B.G.; Zhou Z.K.; Tian J.W.; Yuan A.H. Chin. J. Org. Chem. 2019, 39, 406. (in Chinese)
	( 周建平, 吴保庚, 周志宽, 田蒋为, 袁爱华, 有机化学, 20 19, 39, 406.).
[17]	Tang Z.H.; Zhang C.S.; Zhang L.; Liu D.S. Chem. Bull. 2019, 82, 796. (in Chinese)
	( 唐梓桓, 张财顺, 张磊, 刘道胜, 化学通报, 2019, 82, 796.).
[18]	Guria U.N.; Gangopadhyay A.; Ali S.S.; Maiti K.; Samanta S.K.; Manna S. Anal. Methods 2019, 11, 5357.
[19]	Venkatesh Y.; Das J.; Chaudhuri A.; Karmakar A.; Maiti T.K.; Chem. Commun. 2018, 54, 3106.
[20]	Zhang J.; Ji X.; Zhou J.; Chen Z.; Dong X.; Zhao W. Sens. Actuators B, 2018, 257, 1076.
[21]	Yu Y.; Shu T.; Yu B.; Deng Y.; Fu C.; Gao Y. Sens. Actuators B, 2018, 255, 3170.
[22]	Wu H.W.; Chen Y.Y.; Rao C.H.; Liu C.X. Prog. Chem. 2016, 28, 1501. (in Chinese)
	( 伍宏伟, 陈亚运, 饶才辉, 刘传祥, 化学进展, 2016, 28, 1501.).
[23]	Zlatic K.; Antol I.; Uzelac L.; Drazic A.M.M.; Kralj M.; Bohne C.; Basaric N. ACS Appl. Mater. Interfaces 2020, 12, 347.
[24]	Kumari N.; Dey N.; Bhattacharya S. Analyst 2014, 139, 2370.
[25]	Nunez-Villanueva D.; Hunter C.A. Chem. Sci. 2017, 8, 206.
[26]	Singh P.; Mittal L.S.; Singh H.; Bhargava G.; Kumar S. New J. Chem. 2017, 41, 10281.
[27]	Pierre-Antoine F.; Benjamin B.; Pierre-Henri E.; Julien V.; Karine T.; Rachida Z. Tetrahedron Lett. 2010, 51, 4630.
[28]	Baruah M.; Qin W.W.; Basaric N.; De Borggraeve W.M.; Boens N. J. Org. Chem. 2005, 70, 4152.
[29]	Pettit G.R.; Grealish M.P.; Jung M.K.; Hamel E.; Pettit P.K.; Chapuis J.C.; Schmidt J.M. J. Med. Chem. 2002, 45, 2534.

基于氟引发串联释放的氟硼二吡咯类荧光探针的合成及其识别性能

Synthesis and Recognition Properties of Fluoroborodipyrrole Fluorescent Probes Based on Fluorine Triggered Cascade Releasing

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