Chinese Journal of Organic Chemistry >
Research Progress in Design, Synthesis and Application of Multifunctional Fluorescent Probes
Received date: 2019-01-22
Revised date: 2019-03-08
Online published: 2019-04-09
Supported by
Project supported by the Natural Science Foundation of Guangdong Province (No. 2014A030313429), the Guangzhou Science and Technology Project Scientific Special (No. 201607010251), the Natural Science Foundation of Jiangsu Province (No. BK20160551), the National Natural Science Foundation of China (No. 21602085), the Guangdong Provincial Science and Technology Project (No. 2017A010103016), and the Undergraduates Innovation Project of South China Normal University (No. 20191434).
The multifunctional fluorescent probes can detect a plurality of anions and cations or other small molecules. These probes can greatly improve the detection efficiency and reduce the analysis cost with respect to the mono-analyte fluorescent probes. Thus, they have attracted much attention in recent years. According to their molecular structural characteristics, the reported multifunctional fluorescent probes are divided into three types as organic small molecules, polymers and metal-organic complexes. The new progress on their molecular design, synthesis and detecting application is reviewed on the viewpoint of sensing objects and performances. The developing potential of multifunctional fluorescent probes is envisioned also, and the probes capable of simultaneously identifying multiple analytes in the same system should be highlighted in the future
Chen Sihong , Pang Chuming , Chen Xiaoyun , Yan Zhihao , Huang Shimin , Li Xiangdi , Zhong Yating , Wang Zhaoyang . Research Progress in Design, Synthesis and Application of Multifunctional Fluorescent Probes[J]. Chinese Journal of Organic Chemistry, 2019 , 39(7) : 1846 -1857 . DOI: 10.6023/cjoc201901033
[1] Daly, B.; Ling, J.; de Silva, A. P. Chem. Soc. Rev. 2015, 44, 4023.
[2] Chen, K.; Shu, Q. H.; Schmittel, M. Chem. Soc. Rev. 2015, 44, 136.
[3] Magri, D. C.; Brown, G. J.; McClean, G. D.; de Silva, A. P. J. Am. Chem. Soc. 2006, 128, 4950.
[4] Ma, H. W.; Li, F.; Li, P.; Wang, H. L.; Zhang, M.; Zhang, G.; Baumgarten, M.; Mullen, K. Adv. Funct. Mater. 2016, 26, 2025.
[5] Yin, C.-X.; Xiong, K.-M.; Huo, F.-J.; Salamanca, J. C.; Strongin, R. M. Angew. Chem., Int. Ed. 2017, 56, 13188.
[6] Yin, G. X.; Niu, T. T.; Gan, Y. B.; Yu, T.; Yin, P.; Chen, H. M.; Zhang, Y. Y.; Li, H. T.; Yao, S. Z. Angew. Chem., Int. Ed. 2018, 57, 4991.
[7] 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.)
[8] Jiang, K.; Cao, L.; Hao, Z.-F.; Chen, M.-Y.; Cheng, J.-L.; Li, X.; Xiao, P.; Chen, L.; Wang, Z.-Y. Chin. J. Org. Chem. 2017, 37, 2221(in Chinese). (蒋凯, 曹梁, 郝志峰, 陈美艳, 程洁銮, 李晓, 肖萍, 陈亮, 汪朝阳, 有机化学, 2017, 37, 2221.)
[9] Jun, J. V.; Petersson, E. J.; Chenoweth, D. M. J. Am. Chem. Soc. 2018, 140, 9486.
[10] Li, Z.; Fang, M.; LaGasse, M. K.; Askim, J. R.; Suslick, K. S. Angew. Chem., Int. Ed. 2017, 56, 9860.
[11] Shan, Z.; Lu, M, S.; Wang, L.; MacDonald, B.; MacInnis, J.; Mkandawire, M.; Zhang, X.; Oakes, K. D. Chem. Commun. 2016, 52, 2087.
[12] Wu, Y.-C.; Jiang, K.; Luo, S.-H.; Cao, L.; Wu, H.-Q.; Wang, Z.-Y. Spectrochim. Acta, Part A 2018, 206, 632.
[13] Jiang, K.; Wu, Y.-C.; Wu, H.-Q.; Li, S.-L.; Luo, S.-H.; Wang, Z.-Y. J. Photochem. Photobiol., A 2018, 350, 52.
[14] Li, M.; Lu, H.-Y.; Liu, R.-L.; Chen, J.-D.; Chen, C.-F. J. Org. Chem. 2012, 77, 3670.
[15] Zhang, Y.-Y.; Chen, X.-Z.; Liu, X.-Y.; Wang, M.; Liu, J.-J.; Gao, G.; Zhang, X.-Y.; Sun, R.-Z.; Hou, S.-C.; Wang, H.-M. Sens. Actuators, B 2018, 273, 1077.
[16] Diana, R.; Caruso, U.; Concilio, S.; Piotto, S.; Tuzi, A.; Panunzi, B. Dyes Pigm. 2018, 155, 249.
[17] Wang, Y.; Mao, P.-D.; Wu, W.-N.; Mao, X.-J.; Fan, Y.-C.; Zhao, X.-L.; Xu, Z.-Q.; Xu, Z.-H. Sens. Actuators, B 2018, 255, 3085.
[18] Jung, J. M.; Lee, S. Y.; Kim, C. Sens. Actuators, B 2017, 251, 291.
[19] Hwang, S. M.; Kim, C. Inorg. Chim. Acta 2018, 482, 375.
[20] Hariharan, P. S.; Anthony, S. P. Spectrochim. Acta, Part A 2015, 136, 1658.
[21] Choi, Y. W.; Park, G. J.; Na, Y. J.; Jo, H. Y.; Lee, S. A.; You, G. R.; Kim, C. Sens. Actuators, B 2014, 194, 343.
[22] Hariharan, P. S.; Anthony, S. P. Anal. Chim. Acta 2014, 848, 74.
[23] Li, Y. R.; Wu, J.; Jin, X. J.; Wang, J. W.; Han, S.; Wu, W. Y.; Xu, J.; Liu, W. S.; Yao, X. J.; Tang, Y. Dalton Trans. 2014, 43, 1881.
[24] Song, E. J.; Park, G. J.; Lee, J. J.; Lee, S.; Noh, I.; Kim, Y.; Kim, S. J.; Kim, C.; Harrison, R. G. Sens. Actuators, B 2015, 213, 268.
[25] Kundu, A.; Hariharan, P. S.; Prabakaran, K.; Anthony, S. P. Spectrochim. Acta, Part A 2015, 151, 426.
[26] Pannipara, M.; Al-Sehemi, A. G.; Irfan, A.; Assiri, M.; Kalam, A.; Al-Ammari, Y. S. Spectrochim. Acta, Part A 2018, 201, 54.
[27] Behera, N.; Manivannan, V. J. Photochem. Photobiol., A 2018, 353, 77.
[28] Liao, Z.; Liu, Y.; Han, S.-F.; Wang, D.; Zheng, J.-Q.; Zheng, X.-J.; Jin, L.-P. Sens. Actuators, B 2017, 244, 914.
[29] Jang, H. J.; Kang, J. H.; Yun, D.; Kim, C. J. Fluoresc. 2018, 28, 785.
[30] Tang, X.; Han, J.; Wang, Y.; Ni, L.; Bao, X.; Wang, L.; Zhang, W. L. Spectrochim. Acta, Part A 2017, 173, 721.
[31] Chang, L.-L.; Gao, Q.; Liu,-S.; Hu, C.-C.; Zhou, W.-J.; Zheng, M.-M. Dyes Pigm. 2018, 153, 117.
[32] Su, W.; Yuan, S. Z.; Wang, E. J. J. Fluoresc. 2017, 27, 1871.
[33] Roy, C. B.; Meshram, J. S. J. Lumin. 2016, 171, 208.
[34] Singh, A.; Singh, R.; Shellaiah, M.; Prakash, E. C.; Chang, H. C.; Raghunath, P.; Lin, M. C.; Lin, H. C. Sens. Actuators, B 2015, 207, 338.
[35] Gundogdu, L.; Kose, M.; Takeuchi, S.; Yokoyama, Y.; Orhan, E. J. Lumin. 2018, 203, 568.
[36] Guo, S. L.; Liu, G.; Fan, C. B.; Pu, S. Z. Sens. Actuators, B 2018, 266, 603.
[37] Chen, S.; Wang, W. J.; Yan, M. M.; Tu, Q.; Chen, S. W.; Li, T. B.; Yuan, M. S.; Wang, J. Y. Sens. Actuators, B 2018, 255, 2086.
[38] Wang, L. L.; Qu, Y.; Yang, Y. X.; Cao, J.; Wang, L. Sens. Actuators, B 2018, 269, 78.
[39] Zhang, S. S.; Wu, X. X.; Niu, Q. F.; Guo, Z. R.; Li, T. D.; Liu, H. X. J. Fluoresc. 2017, 27, 729.
[40] Puthiyedath, T.; Bahulayan, D. Sens. Actuators, B 2018, 272, 110.
[41] Sie, Y.-W.; Wan, C.-F.; Wu, A.-T. RSC Adv. 2017, 7, 2460.
[42] Sandhu, S.; Kumar, R.; Tripathi, N.; Singh, H.; Singh, P.; Kumar, S. Sens. Actuators, B 2017, 241, 8.
[43] Magri, D. C.; Fava, M. C.; Mallia, C. J. Chem. Commun. 2014, 50, 1009.
[44] Liang, C. S.; Jiang, S. M. Spectrochim. Acta, Part A 2017, 183, 267.
[45] Li, S. Z.; Huang, D. Y.; Wan, J. Y.; Yan, S. C.; Jiang, J. L.; Xiao, H. B. Sens. Actuators, B 2018, 275, 101.
[46] Jung, J. M.; Kang, J. H.; Han, J.; Lee, H.; Lim, M. H.; Kim, K. T.; Kim, C. Sens. Actuators, B 2018, 267, 58.
[47] Pandith, A.; Bhattarai, K. R.; Kumara, R.; Siddappa, G.; Chae, H.-J.; Seo, Y. J. Sens. Actuators, B 2019, 282, 730.
[48] Feng, X. J.; Fu, Y. L.; Jin, J.; Wu, J. X. Anal. Biochem. 2018, 563, 20.
[49] Xu, J. B.; Liu, N.; Hao, C. W.; Han, Q. Q.; Duan, Y. L.; Wu, J. Sens. Actuators, B 2019, 280, 129.
[50] Padhan, S. K.; Palei, J.; Rana, P.; Murmu, N.; Sahu, S. N. Spectrochim. Acta, Part A 2019, 208, 271.
[51] Tripathi, K.; Singh, A. K.; Sonkar, A. K.; Prakash, A.; Roy, J. K.; Mishra, L.; Sens. Actuators, B 2018, 275, 116.
[52] Wu, W.-N.; Wu, H.; Wang, Y.; Mao, X.-J.; Liu, B.-Z.; Zhao, X.-L.; Xu, Z.-Q.; Fan, Y.-C.; Xu, Z.-H. RSC Adv. 2018, 8, 5640.
[53] Wu, Y.-C.; Huo, J.-P.; Cao, L.; Ding, S.; Wang, L.-Y.; Cao, D. R.; Wang, Z.-Y. Sens. Actuators, B 2016, 237, 865.
[54] Wu, Y.-C.; You, J.-Y.; Jiang, K.; Xie, J.-C.; Li, S.-L.; Cao, D. R.; Wang, Z.-Y. Dyes Pigm. 2017, 140, 47.
[55] Singh, P.; Singh, H.; Bhargava, G.; Kumar, S. J. Mater. Chem. C 2015, 3, 5524.
[56] Joo, D. H.; Mok, J. S.; Bae, G. H.; Oh, S. E.; Kang, J. H.; Kim, C. Ind. Eng. Chem. Res. 2017, 56, 8399.
[57] Ding, W.-H.; Wang, D.; Zheng, X.-J.; Ding, W.-J.; Zheng, J.-Q.; Mu, W.-H.; Cao, W.; Jin, L.-P. Sens. Actuators, B 2015, 209, 359.
[58] Li, L.; Shen, Y.; Zhao, Y.-H.; Mu, L.; Zeng, X.; Redshaw, C.; Wei, G. Sens. Actuators, B 2016, 226, 279.
[59] Zhang, H.; Sun, T.; Ruan, Q.; Zhao, J.-L; Mu, L.; Zeng, X.; Jin, Z. W.; Su, S. B.; Luo, Q. Y.; Yan, Y. Y.; Redshaw, C. Dyes Pigm. 2019, 162, 257.
[60] Ta, S.; Das, S.; Ghosh, M.; Banerjee, M.; Hira, S. K.; Manna, P. P.; Das, D. Spectrochim. Acta, Part A 2019, 209, 170.
[61] Wan, C.-F.; Chang, Y.-J.; Chien, C.-Y.; Sie, Y.-W.; Hu, C.-H.; Wu, A.-T. J. Lumin. 2016, 178, 115.
[62] Wang, Q. M.; Tan, Y. Z.; Wang, N. H.; Lu, Z. X.; Wang, W. L. Spectrochim. Acta, Part A 2018, 201, 216.
[63] Singh, H.; Bhargava, G.; Kumar, S.; Singh, P.; Sens. Actuators, B 2018, 272, 43.
[64] Gwon, S. Y.; Rao, B. A.; Kim, H. S.; Son, Y. A.; Kim, S. H. Spectrochim. Acta, Part A 2015, 144, 226.
[65] Cao, L.; Xiong, J.-F.; Wu, Y.-C.; Ding, S.; Li, M.-B.; Xie, F.; Ma, Z.-H.; Wang, Z.-Y. Chin. J. Org. Chem. 2016, 36, 2053(in Chinese). (曹梁, 熊金峰, 吴彦城, 丁沙, 李铭冰, 谢芬, 马志晗, 汪朝阳, 有机化学, 2016, 36, 2053.)
[66] Su, P. R.; Zhu, Z. W.; Wang, J.; Cheng, B.; Wu, W. Y.; Iqbal, K.; Tang, Y. Sens. Actuators, B 2018, 273, 93.
[67] Kumar, A.; Chae, P. S. Sens. Actuators, B 2019, 281, 933.
[68] Okorochenkova, Y.; Porubsky, M.; Benicka, S.; Hlavac, J. Chem. Commun. 2018, 54, 7589.
[69] Okda, H. E.; Sayed, S. E.; Otri, I.; Ferreora, R. C. M.; Costa, S. P. G.; Raposo, M. M. M.; Martínez-Máñez, R.; Sancenón, F. Dyes Pigm. 2019, 162, 303.
[70] Wu, Y.-C.; Luo, S.-H.; Cao, L.; Jiang, K.; Wang, L.-Y.; Xie, J.-C.; Wang, Z.-Y. Anal. Chim. Acta 2017, 976, 74.
[71] Jiang, K.; Luo, S.-H.; Pang, C.-M.; Wang, B.-W.; Wu, H.-Q.; Wang, Z.-Y. Dyes Pigm. 2019, 162, 367.
[72] Chahal, M. K.; Sankar, M. Dalton Trans. 2017, 46, 11669.
[73] Zhang, X. Y.; Chen, S. S.; Jin, S. H.; Zhang, Y.; Chen, X.; Zhang, Z.; Shu, Q. H. Sens. Actuators, B 2017, 242, 994.
[74] Kumar, V.; Raviraju, G.; Rana, H.; Rao, V. K.; Gupta, A. K. Chem. Commun. 2017, 53, 12954.
[75] Li, H. Q.; Sun, X. Q.; Zheng, T.; Xu, Z. X.; Song, Y. X.; Gu, X. H. Sens. Actuators, B 2019, 279, 400.
[76] Xie, X. X.; Yin, C. X.; Yue, Y. K.; Chao, J. B.; Huo, F. J. Sens. Actuators, B 2018, 277, 647.
[77] Thomas, S. W.; Joly, G. D.; Swager, T. M. Chem. Rev. 2007, 107, 1339.
[78] Geng, T.-M.; Wu, D.-Y.; Huang, W.; Huang, R.-Y.; Wu, G.-H. J Polym Res 2014, 21, 354.
[79] Chen, H.; Dai, W.; Huang, J. X.; Chen, S. J.; Yan, X. H. J. Mater. Sci. 2018, 53, 15717.
[80] Guo, Z. Q.; Zhu, W. H.; Tian, H. Macromol. 2010, 43, 739.
[81] Geng, T.-M.; Wu, D.-Y.; Huang, W. J. Polym. Res. 2015, 22, 40.
[82] Geng, T.-M.; Wang, X.; Jiang, H.; Song, W.; Ni, R. F.; Chen, J.; Wang, Y. J. Fluoresc. 2016, 26, 977.
[83] Hu, J. M.; Dai, L.; Liu, S. Y. Macromol. 2011, 44, 4699.
[84] Guo, C. X.; Li, P.; Pei, M. S.; Zhang, G. Y. Sens. Actuators, B 2015, 221, 1223.
[85] Wang, L. Y.; Fang, G. P.; Cao, D. R. Sens. Actuators, B 2015, 221, 63.
[86] Wang, T. S.; Zhang, N.; Li, Q. B.; Li, Z. L.; Bao, Y. Y.; Bai, R. K. Sens. Actuators, B 2016, 225, 81.
[87] Bao, Y. Y.; Wang, T. S.; Li, Q. B.; Du, F. F.; Bai, R. K.; Smet, M.; Dehaen, W. Polym. Chem. 2014, 5, 792.
[88] Ju, P. Y.; Su, Q.; Liu, Z. Q.; Li, X. D.; Guo, B. X.; Liu, W. T.; Li, G. H.; Wu, Q. L. J. Mater. Sci. 2019, 54, 851.
[89] Qu, J.-B.; Li, S.-H.; Xu, Y.-L.; Liu, Y.; Liu, J.-G. Sens. Actuators, B 2018, 272, 124.
[90] Kumar, V. V.; Thenmozhi, M. K.; Ganesan, A.; Ganesan, S. S.; Anthony, S. P. RSC Adv. 2015, 5, 88125.
[91] Ding, P.; Xin, X.; Zhao, L. L.; Xie, Z. C.; Zhang, Q. H.; Jiao, J. M.; Xu, G. Y. RSC Adv. 2017, 7, 3051.
[92] Wu, Z.-F.; Gong, L.-K.; Huang, X.-Y. Inorg. Chem. 2017, 56, 7397.
[93] Hu, J.-S.; Dong, S.-J.; Wu, K.; Zhang, X.-L.; Jiang, J.; Yuan, J.; Zheng, M.-D. Sens. Actuators, B 2018, 283, 255.
[94] Chen, K.; Schmittel, M. Analyst 2013, 138, 6742.
[95] Liu, Y.; Ma, J. J.; Xu, C.; Yang, Y.; Xia, M. F.; Jiang, H.; Liu, W. S. Dalton Trans. 2018, 47, 13543.
[96] Yang, Y.; Qiu, F. Z.; Xu, C.; Feng, Y.; Zhang, G. L.; Liu, W. S. Dalton Trans. 2018, 47, 7480.
[97] Yang, C. L.; Xu, J.; Ma, J. Y.; Zhu, D. Y.; Zhang, Y. F.; Liang, L. Y.; Lü, M. G. Polym. Chem. 2012, 3, 2640.
[98] Yang, Y.; Song, X. R.; Xu, C.; Wang, Y. Z.; Zhang, G. L.; Liu, W. S. Dalton Trans. 2018, 47, 11077.
[99] Pang, C.-M.; Luo, S.-H.; Hao, Z.-F.; Gao, J.; Huang, Z.-H.; Yu, J.-H.; Yu, S.-M.; Wang, Z.-Y. Chin. J. Org. Chem. 2018, 38, 2606(in Chinese). (庞楚明, 罗时荷, 郝志峰, 高健, 黄召昊, 余家海, 余思敏, 汪朝阳, 有机化学, 2018, 38, 2606.)
[100] Wu, Z.-F.; Huang, X.-Y. Dalton Trans. 2017, 46, 12597.
[101] Dalapati, R.; Biswas, S. Sens. Actuators, B 2017, 239, 759.
[102] Li, H. H.; Han, Y. B.; Shao, Z. C.; Li, N.; Huang, C.; Hou, H. W. Dalton Trans. 2017, 46, 12201.
[103] Li, J.-M.; Li, R.; Li, X. CrystEngComm 2018, 20, 4962.
[104] Shi, M.; Yang, J.; Liu, Y.-Y.; Ma, J.-F. Dyes Pigm. 2016, 129, 109.
[105] Chen, S. G.; Shi, Z. Z.; Qin, L.; Jia, H. L.; Zheng, H. G. Cryst. Growth Des. 2017, 17, 67.
[106] Gong, W.-J.; Yao, R.; Li, H.-X.; Ren, Z.-G.; Zhang, J.-G.; Lang, J.-P. Dalton Trans. 2017, 46, 16861.
[107] Natarajan, S.; Jana, A. K. ChemPlusChem 2017, 82, 1153.
[108] Wang, X. R.; Huang, Z.; Du, J.; Wang, X. Z.; Gu, N.; Tian, X.; Li, Y.; Liu, Y. Y.; Huo, J. Z.; Ding, B. Inorg. Chem. 2018, 57, 12885.
[109] Wang, X. R.; Du, J.; Huang, Z.; Liu, K.; Liu, Y. Y.; Huo, J. Z.; Liu, Z. Y.; Dong, X. Y.; Chen, L. L.; Ding, B. J. Mater. Chem. B 2018, 6, 4569.
[110] Li, B.; Chen, X.; Hu, P.; Kirchon, A.; Zhao, Y.-M.; Pang, J. D.; Zhang, T. L.; Zhou, H.-C. ACS Appl. Mater. Interfaces 2019, 11, 8227.
[111] Dong, B.-X.; Pan, Y.-M.; Liu, W.-L.; Teng, Y.-L. Cryst. Growth Des. 2018, 18, 431.
[112] Erdemir, S.; Kocyigi, T. O. Sens. Actuators, B 2018, 273, 56.
[113] Moghadam, F. N.; Amirnasr, M.; Meghdadi, S.; Eskandari, K.; Buchholz, A.; Plass, W. Spectrochim. Acta, Part A 2019, 207, 6.
[114] Ekbote, A.; Mobin, S. M.; Misra, R. J. Mater. Chem. C 2018, 6, 10888.
[115] Kundu, B. K.; Mandal, P.; Mukhopadhyay, B. G.; Tiwari, R.; Nayak, D.; Ganguly, R. Sens. Actuators, B 2019, 282, 347.
[116] Chen, L.; Oh, H.; Wu, D.; Kim, M. H.; Yoon, J. Chem. Commun. 2018, 34, 2276.
[117] TG, A. K.; Tekuria, V.; Mohan, M.; Trivedi, D. R. Sens. Actuators, B 2019, 284, 271.
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