Reviews

New Progress in the Design, Synthesis and Application of Fluorescent Probes for Fluoride Ion Detection

  • Zhang Huimin ,
  • Wu Yancheng ,
  • You Jiayi ,
  • Cao Liang ,
  • Ding Sha ,
  • Jiang Kai ,
  • Wang Zhaoyang
Expand
  • Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, School of Chemistry and Environment, South China Normal University, Guangzhou 510006

Received date: 2016-06-06

  Revised date: 2016-06-28

  Online published: 2016-07-15

Supported by

Project supported by the Natural Science Foundation of Guangdong Province (No.2014A030313429) and the 3rd Talents Special Funds of Guangdong Higher Education (No.Guangdong-Finance-Education[2011]431),Guangzhou Science and Technology Project Scientific Special (No.201607010251).

Abstract

The recognition and detection of trace fluoride ions in vivo and vitro have attracted great attention in recent years. More and more new fluorescent probes (FP) for fluoride ion detection have been designed and synthesized due to their advantages, such as high sensitivity, good selectivity and convenient operation. According to the different structural features and recognition mechanism, fluoride ion FP can be classified into two categories as deprotonation and reaction type. The new progress especially in recent three years on their molecular design, synthesis and application is reviewed on the viewpoint of green chemistry. The future trend of fluoride ion FP is also prospected.

Cite this article

Zhang Huimin , Wu Yancheng , You Jiayi , Cao Liang , Ding Sha , Jiang Kai , Wang Zhaoyang . New Progress in the Design, Synthesis and Application of Fluorescent Probes for Fluoride Ion Detection[J]. Chinese Journal of Organic Chemistry, 2016 , 36(11) : 2559 -2582 . DOI: 10.6023/cjoc201606012

References

[1] Kaur, K.; Mittal, S. K.; Kumar, S. K. A.; Kumar, A.; Kumar, S. Anal. Methods 2013, 5, 5565.
[2] Brugnara, A.; Topic, F.; Rissanen, K.; de La Lande, A.; Colasson, B.; Reinaud, O. Chem. Sci. 2014, 5, 3897.
[3] Langton, M. J.; Serpell, C. J.; Beer, P. D. Angew. Chem., Int. Ed. 2015, 55, 1974.
[4] Wu, S.-Z.; Han, T.-Y.; Guo, J.-J.; Cheng, Y.-S. Sens. Actuators, B 2015, 220, 1305.
[5] Mani, V.; Li, W.-Y.; Gu, J.-A.; Lin, C.-M.; Huang, S.-T. Talanta 2015, 131, 121.
[6] Cametti, M; Rissanen, K. Chem. Commun. 2009, 2809.
[7] Cametti, M.; Rissanen, K. Chem. Soc. Rev. 2013, 42, 2016.
[8] Manjare, S. T; Kim, Y; Churchill, D. G. Acc. Chem. Res. 2014, 47, 2985.
[9] Zhou, Y.; Zhang, J. F.; Yoon, J. Chem. Rev. 2014, 114, 5511.
[10] Jiao, Y.; Zhu, B.-C.; Chen, J.-H.; Duan, X.-H. Theranostics 2015, 5, 173.
[11] Zhen, W.; Ying, Z.; Jun, R. Chem. Sens. 2012, 32, 41 (in Chi-nese). (吴振, 周应, 任君, 化学传感器, 2012, 32, 41.)
[12] Li, Y.-J.; Xie, D.-Y.; Pang, X.-L.; Yu, X.-D.; Yu, T.; Ge, X.-T. Sens. Actuators, B 2016, 227, 660.
[13] Sun, J.-Q.; Ye, B.-F.; Xia, G.-M.; Zhang, X.-H.; Wang, H.-M. Sens. Actuators, B 2016, 233, 76.
[14] Bhoi, A. K.; Das, S. K.; Majhi, D.; Sahu, P. K.; Nijamudheen, A.; Anoop, N.; Rahaman, A.; Sarkar, M. J. Phys. Chem. B 2014, 118, 9926.
[15] Hu, J.-M.; Li, C.-H.; Cui, Y.; Liu, S.-Y. Macromol. Rapid Commun. 2011, 32, 610.
[16] Saravanan, C.; Easwaramoorthi, S.; Hsiow, C. Y.; Wang, K.; Hayashi, M.; Wang, L. Org. Lett. 2014, 16, 354.
[17] Sivaraman, G.; Chellappa, D. J. Mater. Chem. B 2013, 1, 5768.
[18] Wu, Y.-C.; You, J.-Y.; Guan, L.-T. Shi, J.; Cao, L.; Wang, Z.-Y. Chin. J. Org. Chem. 2015, 35, 2465 (in Chinese). (吴彦城, 尤嘉宜, 关丽涛, 石杰, 曹梁, 汪朝阳, 有机化学, 2015, 35, 2465.)
[19] Batista, R. M. F.; Costa, S. P. G.; Raposo, M. M. M. J. Photo-chem. Photobiol. A 2013, 259, 33.
[20] Ali, R.; Razi, S. S.; Gupta, R. C.; Dwivedi, S. K.; Misra, A. New J. Chem. 2016, 40, 162.
[21] Hu, J.-Y.; Liu, R.; Zhu, X.-L.; Cai, X.; Zhu, H.-J. Chin. Chem. Lett. 2015, 26, 339.
[22] Xiong, J.; Cui, L.; Liu, W.; Beves, J. E.; Li, Y.-Y.; Zuo, J.-L. Tetrahedron Lett. 2013, 54, 1998.
[23] Yang, C.-L.; Xu, J.; Li, J.-Y.; Lu, M.-G.; Li, Y.-B.; Wang, X.-L. Sens. Actuators, B 2014, 196, 133.
[24] Liu, T.; Nonat, A.; Beyler, M.; Regueiro-Figueroa, M.; Nono, K. N.; Jeannin, O.; Camerel, F.; Debaene, F.; Cianferani-Sanglier, S.; Tripier, R. Angew. Chem., Int. Ed. 2014, 53, 7259.
[25] Sarkar, A.; Bhattacharyya, S.; Mukherjee, A. Dalton Trans. 2016, 45, 1166.
[26] Parthiban, C.; Ciattini, S.; Chelazzi, L.; Elango, K. P. Sens. Actuators, B 2016, 231, 768.
[27] Parthiban, C.; Elango, K. P. Sens. Actuators, B 2015, 215, 544.
[28] Pazik, A.; Skwierawska, A. Supramol. Chem. 2013, 25, 189.
[29] Yang, X.-F.; Zhang, G.-G.; Li, Y.-X.; Liu, Z.; Gong, X.-Q.; Gao, B.; Zhang, G.-Y.; Cui, Y.; Sun, G.-X. RSC Adv. 2015, 5, 22455.
[30] Uahengo, V.; Xiong, B.; Cai. P.; Daniel, L. S. Rhyman, L.; Ramasami, P. Anal. Chem. Res. 2016, 8, 1.
[31] Yang, X.-F.; Xie, L.-J.; Ning, R.; Gong, X.-Q.; Liu, Z.; Li, Y.-X.; Zheng, L.-Y.; Zhang, G.-G.; Gao, B.; Cui, Y.; Sun, G.-X.; Zhang, G.-Y. Sens. Actuators, B 2015, 210, 784.
[32] Niu, H.; Shu, Q.-H.; Jin, S.-H.; Li, B.-J.; Zhu, J.-P.; Li, L.-J.; Chen, S.-S. Spectrochim. Acta, Part A 2016, 153, 194.
[33] Chetia, B.; Iyer, P. K. Sens. Actuators, B 2014, 201, 191.
[34] Liu, X.-M.; Zhao, Q.; Li, Y.; Song, W.-C.; Li, Y.-P.; Chang, Z.; Bu, X.-H. Chin. Chem. Lett. 2013, 24, 962.
[35] Jeyanthi, D.; Iniya, M.; Krishnaveni, K.; Chellappa, D. Spectrochim. Acta, Part A 2015, 136, 1269.
[36] Anand, T.; Sivaramana, G.; Iniya, M.; Siva, A.; Chellappa, D. Anal. Chim. Acta 2015, 876, 1.
[37] Lee, J. Y.; Rao, B. A.; Hwang, J. Y.; Son, Y. A. Sens. Actuators, B 2015, 220, 1070.
[38] Vinithra, G.; Suganya, S.; Velmathi, S. Tetrahedron Lett. 2013, 54, 5612.
[39] Satheshkumar, A.; Elango, K. P. Dyes Pigm. 2013, 96, 364.
[40] Kumar, S. M.; Dhahagani, K.; Rajesh, J. Nehru, K.; Annaraj, J.; Chakkaravarthi, G.; Rajagopal, G. Polyhedron 2013, 59, 58.
[41] Ashokkumar, P.; Weisshoff, H.; Kraus, W.; Rurack, K. Angew. Chem., Int. Ed. 2014, 53, 2225.
[42] Yan, X.-Q.; Zhuo, J.-B.; Wang, J.-C.; Yuan, Y.-F. Chin. J. Org. Chem. 2015, 35, 2184 (in Chinese). (晏希泉, 卓继斌, 王吉成, 谢莉莉, 袁耀锋, 有机化学, 2015, 35, 2184.)
[43] Basheer, S. M.; Willis, A. C.; Pace, R. J.; Sreekanth, A. Polyhedron 2016, 109, 7.
[44] Sharma, S.; Hundal, M. S.; Hundal, G. Tetrahedron Lett. 2013, 54, 2423.
[45] Yang, X.-F.; Zheng, L.-Y.; Xie, L.-J.; Liu, Z.; Li, Y.-X.; Ning, R.; Zhang, G.-G.; Gong, X.-Q.; Gao, B.; Liu, C.-X.; Cui, Y.; Sun, G.-X.; Zhang, G.-Y. Sens. Actuators, B 2015, 207, 9.
[46] Mahapatra, A. K.; Karmakar, P.; Roy, J.; Manna, S.; Maiti, K.; Sahoo, P.; Mandal, D. RSC Adv. 2015, 5, 37935.
[47] Biswas, S.; Gangopadhyay, M.; Barman, S.; Sarkar, J.; Singh, N. D. P. Sens. Actuators, B 2016, 222, 823.
[48] Liu, Y.-W.; Kao, M.-X.; Wu, A.-T. Sens. Actuators, B 2015, 208, 429.
[49] Goswami, S.; Maity, S.; Maity, A. C.; Das, A. K.; Pakhira, B.; Khanra, K.; Bhattacharyya, N.; Sarkar, S. RSC Adv. 2015, 5, 5735.
[50] Singh, J.; Yadav, M.; Singh, A.; Singh, N. Dalton Trans. 2015, 44, 12589.
[51] Mori, H.; Takahashi, E.; Ishizuki, A.; Nakabayashi, K. Macromolecules 2013, 46, 6451.
[52] Erdemir, S.; Kocyigit, O.; Alici, O.; Malkondu, S. Tetrahedron Lett. 2013, 54, 613.
[53] Sharma, R.; Mittal, S. K.; Chhibber, M. J. Electrochem. Soc. 2015, 162, B248.
[54] Maiti, D. K.; Roy, S.; Datta, A.; Banerjee, A. Chem. Phys. Lett. 2013, 588, 76.
[55] Khanmohammadi, H.; Rezaeian, K. RSC Adv. 2014, 4, 1032.
[56] Alam, P.; Kachwal, V.; Laskar, I. R. Sens. Actuators, B 2016, 228, 539.
[57] Suganya, S.; Velmathi, S. J. Mol. Recognit. 2013, 26, 259.
[58] Na, Y. J.; Choi, Y. W.; Yun, J. Y.; Park, K. M.; Chang, P. S.; Kim, C. Spectrochim. Acta, Part A 2015, 136, 1649.
[59] Song, E. J.; Kim, H.; Hwang, I. H.; Kim, K. B.; Kim, A. R.; Noh, I.; Kim, C. Sens. Actuators, B 2014, 195, 36.
[60] Lin, Q.; Yang, Q.-P.; Sun, B.; Lou, J.-C.; Wei, T.-B.; Zhang, Y.-M. RSC Adv. 2015, 5, 11786.
[61] Yan, G.-T.; Wu, G.-Y.; Qu, W.-J.; Shi, B.-B.; Lin, Q.; Yao, H.; Zhang, Y.-M.; Wei, T.-B. Supramol. Chem. 2016, 27, 552.
[62] Liu, R.-Y.; Gao, Y.; Zhang, Q.-B.; Yang, X.-D.; Lu, X.-W.; Ke, Z.-Y.; Zhou, W.-Q.; Qu, J.-Q. New J. Chem. 2014, 38, 2941.
[63] Zheng, X.-J.; Zhu, W.-C.; Liu, D.; Ai, H.; Huang, Y.; Lu, Z.-Y. ACS Appl. Mater. Interfaces 2014, 6, 7996.
[64] Ghosh, D.; Rhodes, S.; Hawkins, K.; Winder, D.; Atkinson, A.; Ming, W. H.; Padgett, C.; Orvis, J.; Aiken, K.; Landge, S. New J. Chem. 2015, 39, 295.
[65] Balamurugan, A; Lee, H. I. Sens. Actuators, B 2015, 216, 80.
[66] Mahapatra, A. K.; Maiti, K.; Sahoo, P.; Nandi, P. K. J. Lumin. 2013, 143, 349.
[67] Liu, C.-X.; Xu,-J.; Yang, F.; Zhou,W.; Li, Z.-X.; Wei, L.-H.; Yu, M.-M. Sens. Actuators, B 2015, 212, 364.
[68] Ghosh, P.; Kumar, N.; Mukhopadhyay, S. K.; Banerjee, P. Sens. Actuators, B 2016, 224, 899.
[69] Kumar, D.; Thomas, K. R. J. RSC Adv. 2014, 4, 56466.
[70] Xu, S.-Y.; Sun, X.-L.; Ge, H.-B.; Arrowsmith, R. L.; Fossey, J. S.; Pascu, S. I.; Jiang, Y.-B.; James, T. D. Org. Biomol. Chem. 2015, 13, 4143.
[71] Iniya, M.; Jeyanthi, D.; Krishnaveni, K.; Chellappa, D. J. Lumin. 2015, 157, 383.
[72] Kanagaraj, K.; Pitchumani, K. Chem. Asian J. 2014, 9, 146.
[73] Sen Gupta, A.; Paul, K.; Luxami, V. Spectrochim. Acta, Part A 2015, 138, 67.
[74] Wang, Y.; Zhao, Q.; Zang, L.-B.; Liang, C.-S.; Jiang, S.-M. Dyes Pigm. 2015, 123, 166.
[75] Ponnuvel, K.; Padmini,V. J. Lumin. 2016, 169, 289.
[76] Zou, C.-Y.; Qiao, Q.-L.; Zhao, M.; Mao, D.-Q.; Wang, D.-F.; Feng, L.; Cui, J.-N.; Xu, Z.-C. RSC Adv. 2014, 4, 43746.
[77] Li, Y.-H.; Duan, Y.; Zheng, J.; Li, J.-S.; Zhao, W.-J.; Yang, S.; Yang, R.-H. Anal. Chem. 2013, 85, 11456.
[78] Hu, R.; Feng, J.-A.; Hu, D.-H.; Wang, S.-Q.; Li, S.-Y.; Li, Y.; Yang, G.-Q. Angew. Chem., Int. Ed. 2010, 49, 4915.
[79] Calderon-Ortiz, L. K.; Tauscher, E.; Bastos, E. L.; Gorls, H.; Weiss, D.; Beckert, R. Eur. J. Org. Chem. 2012, 2535.
[80] Ke, B.-W.; Chen, W.-X.; Ni, N.-T.; Cheng, Y.-F.; Dai, C.-F.; Dinh, H.; Wang, B.-H. Chem. Commun. 2013, 49, 2494.
[81] Roy, A.; Kand, D.; Saha, T.; Talukdar, P. Chem. Commun. 2014, 50, 5510.
[82] Roy, A.; Kand, D.; Saha, T.; Talukdar, P. RSC Adv. 2014, 4, 33890.
[83] Roy, A.; Datar, A.; Kand, D.; Saha, T.; Talukdar, P. Org. Biomol. Chem. 2014, 12, 2143.
[84] Wu, Z.-S.; Tang, X.-J. Anal. Chem. 2015, 87, 8613.
[85] Turan, I. S.; Akkaya, E. U. Org. Lett. 2014, 16, 1680.
[86] Hou, P.; Chen, S.; Song, X.-Z. Luminescence 2014, 29, 423.
[87] Hou, P.; Chen, S.; Wang, H.-B.; Wang, J.-X.; Voitchovsky, K.; Song, X.-Z. Chem. Commun. 2014, 50, 320.
[88] Zhang, S.-L.; Fan, J.-L.; Zhang, S.-Z.; Wang, J.-Y.; Wang, X.-W.; Du, J.-J.; Peng, X.-J. Chem. Commun. 2014, 50, 14021.
[89] Peng, Y.; Dong, Y.-M.; Dong, M.; Wang, Y.-W. J. Org. Chem. 2012, 77, 9072.
[90] Wang, C.-Y.; Yang, S.; Yi, M.; Liu, C.-H.; Wang, Y.-J.; Li, J.-S.; Li, Y.-H.; Yang, R.-H. ACS Appl. Mater. Interfaces 2014, 6, 9768.
[91] Wu, X.-X.; Niu, Q.-F.; Li, T.-D. Sens. Actuators, B 2016, 222, 714.
[92] Huang, Y.-C.; Chen, C.-P.; Wu, P.-J.; Kuo, S.-Y.; Chan, Y.-H. J. Mater. Chem. B 2014, 2, 6188.
[93] Cheng, X.-H.; Jia, H.-Z.; Feng, J.; Qin, J.-G.; Li, Z. Sens. Actuators, B 2014, 199, 54.
[94] Zheng, F.-Y.; Zeng, F.; Yu, C.-M.; Hou, X.-F.; Wu, S.-Z. Chem. Eur. J. 2013, 19, 936.
[95] Dhanunjayarao, K.; Mukundam, V.; Venkatasubbaiah, K. Sens. Actuators, B 2016, 232, 175.
[96] Yang, S.-J.; Liu, Y.; Feng, G.-Q. RSC Adv. 2013, 3, 20171.
[97] Li, L.; Ji, Y.-Z.; Tang, X.-J. Anal. Chem. 2014, 86, 10006.
[98] Yeh, J.-T.; Venkatesan, P.; Wu, S.-P. New J. Chem. 2014, 38, 6198.
[99] Kumari, N; Dey, N; Bhattacharya, S. Analyst 2014, 139, 2370.
[100] Imsick, B. G.; Acharya, J. R.; Nesterov, E. E. Chem. Commun. 2013, 49, 7043.
[101] Ning, Y.-N.; Wang, B.; Mao, G.-L. Chem. Eng. 2014, (9), 66 (in Chinese). (宁英男, 王斌, 毛国梁, 化学工程师, 2014, (9), 66.)
[102] Xu, J.; Sun, S.-B.; Li, Q.; Yue, Y.; Li, Y.-D.; Shao, S.-J. Anal. Chim. Acta 2014, 849, 36.
[103] Wongsan, W.; Aeungmaitrepirom, W.; Chailapakul, O.; Ngeontae, W.; Tuntulani, T. Electrochim. Acta 2013, 111, 234.
[104] Mou, X.; Liu, S.-J.; Dai, C.-L.; Ma, T.-C.; Zhao, Q.; Ling, Q.-D.; Huang, W. Sci. Sin. Chim. 2010, 40, 979 (in Chinese). (牟鑫, 刘淑娟, 戴春雷, 马廷春, 赵强, 凌启淡, 黄维, 中国科学:化学, 2010, 40, 979.)
[105] Cheng, F.; Bonder, E.M.; Jakle, F. J. Am. Chem. Soc. 2013, 135, 17286.
[106] Liu, X.-L.; Mao, M.; Ren, M.-G.; Tong, Y.; Song, Q.-H. Sens. Actuators, B 2014, 200, 317.
[107] Yuan, M.-S.; Wang, Q.; Wang, W.-J.; Wang, D.-E.; Wang, J.-R.; Wang, J.-Y. Analyst 2014, 139, 1541.
[108] Liu, S.-J.; Zhao, Q.; Xu, W.-J.; Huang, W. Prog. Chem. 2008, 20, 1708 (in Chinese). (刘淑娟, 赵强, 许文娟, 黄维, 化学进展, 2008, 20, 1708.)
[109] Zhang, G.-J.; Wang, L.-M.; Cai, X.-F.; Zhang, L.; Yu, J.-J.; Wang, A.-L. Dyes Pigm. 2013, 98, 232.
[110] Wu, S.-Y.; Chen, Z.-J.; Zhang, K.-W.; Hong, G.; Zhao, G.-S.; Wang, L.-M. Tetrahedron Lett. 2016, 57, 1390.
[111] Wang, L.-Y.; Fang, G.-P.; Cao, D.-R. Sens. Actuators, B 2015, 221, 63.
[112] Misra, R.; Jadhav, T.; Dhokale, B.; Mobin, S. M. Dalton Trans. 2015, 44, 16052.
[113] Wang, L.-Y.; Li, L.-Q.; Cao, D.-R. Sens. Actuators, B 2016, 228, 347.
[114] Boxi, S. S.; Paria, S. Dalton Trans. 2015, 45, 811.
[115] Wang, H.; Hu, T.-Y.; Zhao, Z.-T.; Zhang, X.-Y.; Wang, Y.; Duan, X.-Q.; Liu, D.-W.; Jing, L.; Ma, Q. Talanta 2016, 149, 285.
[116] Dong, X.-L.; Zhou, Y.-H.; Song, Y.-M.; Qu, J.-P. J. Fluorine Chem. 2015, 178, 61.
[117] Bhalla, V.; Gupta, A.; Kumar, M. Talanta 2013, 105, 152.
[118] Liu, J.; Xie, Y.-Q.; Lin, Q.; Shi, B.-B.; Zhang, P.; Zhang, Y.-M.; Wei, T.-B. Sens. Actuators, B 2013, 186, 657.
[119] Kar, C.; Samanta, S.; Mukherjee, S.; Datta, B.K.; Ramesh, A.; Das, G. New J. Chem. 2014, 38, 2660.
[120] Maity, S. B.; Bharadwaj, P. K. Inorg. Chem. 2013, 52, 1161.
[121] Sen, B.; Mukherjee, M.; Banerjee, S.; Pal, S.; Chattopadhyay, P. Dalton Trans. 2015, 44, 8708.
[122] Razi, S. S.; Srivastava, P.; Ali, R.; Gupta, R. C.; Dwivedi, S. K.; Misra, A. Sens. Actuators, B 2015, 209, 162.
[123] Kaur, M.; Cho, M. J.; Choi, D. H. Dyes Pigm. 2014, 103, 154.
[124] Hu, J.-Y.; Liu, R.; Cai, X.; Shu, M.-L.; Zhu, H.-J. Tetrahedron 2015, 71, 3838.
[125] Hinterholzinger, F. M.; Ruhle, B.; Wuttke, S.; Karaghiosoff, K.; Bein, T. Sci. Rep. 2013, 3, 2562.
[126] Bineci, M.; Baglan, M.; Atilgan, S. Sens. Actuators, B 2016, 222, 315.
[127] Kim, H. Y.; Im, H. G.; Chang, S. K. Dyes Pigm. 2015, 112, 170.
[128] Wang, Z.-Y.; Li, J.-N.; Zhao, Y.-M. Green Chemistry General Course, China Textile Press, Beijing, 2007 (in Chinese). (汪朝阳, 李景宁, 赵耀明, 绿色化学通用教程, 中国纺织出版社, 北京, 2007.)
[129] Wu, Y.-C.; Huo, J.-P.; Cao, L.; Ding, S.; Wang, L.-Y.; Cao, D.-R.; Wang, Z.-Y. Sens. Actuators 2016, 237, 865.
[130] Yang, K.; Wang, Z.-Y.; Fu, J.-H.; Tan, Y.-H. Prog. Chem. 2010, 22, 2126 (in Chinese). (杨凯, 汪朝阳, 傅建花, 谭越河, 化学进展, 2010, 22, 2126.)

Outlines

/