Principle and the Research Progress of Fluorescent Chemosensors for Cations Recognition

doi:10.6023/cjoc201402037

Abstract

Fluorescent chemosensors received more and more attention because these kinds of chemosensors possess a lot of advantages such as high sensitivity, realize tele-monitor and real-time detection. It was also used as signal output in ion recognition. With the rapid development of host-guest chemistry, a series of fluorescent sensors with good properties have been reported. In this review the research progress of fluorescent chemosensors in terms of recognition principle for ion recognition in resent five years was briefly reviewed based on intramolecular charge transfer (ICT), photoinduced electron transfer (PET), fluorescence resonance energy transfer (FRET), excited-state intramolecular proton transfer (ESIPT), monomer-excimer (EM) and chelation-enhanced fluorescence (CHEF), etc. The developing orientation for further research is presented.

Key words: fluorescent sensor, ion recognition, intramolecular charge transfer (ICT), photoinduced electron transfer (PET), fluorescence resonance energy transfer (FRET), excited-state intramolecular proton transfer (ESIPT), monomer-excimer, chelation-enhanced fluorescence (CHEF)

Cite this article

Zhang Peng, Zhang Youming, Lin Qi, Yao Hong, Wei Taibao. Principle and the Research Progress of Fluorescent Chemosensors for Cations Recognition[J]. Chin. J. Org. Chem., 2014, 34(7): 1300-1321.

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References

[1] Yang, X. B.; Ge, J. F.; Xu, Q. F.; Zhu, X. L.; Li, N. J.; Gu, H. W.; Lu, J. M. Tetrahedron Lett. 2011, 52, 2492.

[2] Chen, H. H.; Chen, Y. Z.; Li, Z. J.; Yang, Q. Z.; Xin, L. Chin. J. Org. Chem. 2012, 32, 46 (in Chinese).

(陈红海, 陈玉哲, 李仲谨, 杨清正, 辛利, 有机化学, 2012, 32, 46.)

[3] Liu, M.; Tan, H. L.; Liu, Z. G.; Wang, W.; Zeng, W. B. Chin. J. Org. Chem. 2013, 33, 1655 (in Chinese).

(刘敏, 谭慧龙, 刘治国, 王维, 曾文彬, 有机化学, 2013, 33, 1655.)

[4] Kim. J. S.; Quang, D. T. Chem. Rev. 2007, 107, 3780.

[5] Yuan, L.; Lin, W. Y.; Zheng, K. B.; Zhu, S. S. Acc. Chem. Res. 2013, 46, 1462.

[6] Jia, J.; Tang, X.; He, Y. F.; Zhang, M. Y.; Xing, G. W. Chin. J. Org. Chem. 2012, 32, 1803 (in Chinese).

(郏佳, 唐茜, 何颖芳, 张梦雨, 邢国文, 有机化学, 2012, 32, 1803.)

[7] Lin, Q.; Chen, P.; Liu, J.; Fu, Y. P.; Zhang, Y. M.; Wei, T. B. Prog. Chem. 2013, 7, 1177 (in Chinese).

(林奇, 陈佩, 刘娟, 符永鹏, 张有明, 魏太保, 化学进展, 2013, 7, 1177.)

[8] Chen, X. Q.; Pradhan, T.; Wang, F.; Kim, J. S.; Yoon, J. Chem. Rev. 2012, 112, 1910.

[9] Qian, F.; Zhang, C. L.; Zhang, Y. M.; He, W. J.; Gao, X.; Hu, P.; Guo, Z. J. J. Am. Chem. Soc. 2009, 131, 1460.

[10] Goswami, S.; Sen, D.; Das, N. K. Org. Lett. 2010, 12, 856.

[11] Zhu, M.; Yuan, M. J.; Liu, X. F.; Xu, J. L.; Lv, J.; Huang, C. S.; Liu, H. B.; Li, Y. L.; Wang, S.; Zhu, D. B. Org. Lett. 2008, 10, 1481.

[12] Taki, M.; Desaki, M.; Ojida, A.; Iyoshi, S.; Hirayama, T.; Hamachi, I.; Yamamoto, Y. J. Am. Chem. Soc. 2008, 130, 12564.

[13] Debabrata, M.; Govindaraju, T. Inorg. Chem. 2010, 49, 7229.

[14] Li, Q. Q.; Peng, M.; Li, H. Y.; Zhong, C.; Zhang, L.; Cheng, X. H.; Peng, X. N.; Wang, Q. Q.; Qin, J. G.; Li, Z. Org. Lett. 2012, 14, 2094.

[15] Jiang, J.; Liu, W.; Cheng, J.; Yang, L. Z.; Jiang, H. E.; Bai, D. C.; Liu, W. S. Chem. Commun. 2012, 48, 8371.

[16] Feng, X. J.; Tian, P. Z.; Xu, Z.; Chen, S. F.; Wong, M. S. J. Org. Chem. 2013, 78, 11318.

[17] Goswami, S.; Sen, D.; Aich, K. Tetrahedron Lett. 2013, 54, 4620.

[18] Chen, X. F.; Wang, J, Y.; Cui, J. N.; Xu, Z. C.; Peng, X. J. Tetrahedron 2011, 67, 4869.

[19] Hatai, J.; Pal, S.; Jose, G. P.; Bandyopadhyay, S. Inorg. Chem. 2012, 51, 10129.

[20] Helal, A.; Rashid, M. H.; Choi, C. H.; Kim, H. S. Tetrahedron 2011, 67, 2794.

[21] Lohani, C. R.; Kim, J. M.; Lee, K. H. Tetrahedron 2011, 67, 4130.

[22] He, H.; Ng, D. K. P. Chem. Asian J. 2013, 8, 1441.

[23] Zhang, Y. M.; Shi, B. B.; Zhang, P.; Huo, J. Q.; Chen, P.; Lin, Q.; Liu, J.; Wei, T. B. Sci. China Chem. 2013, 56, 612.

[24] Lin, Q.; Liu, X.; Wei, T. B.; Zhang, Y. M. Sens. Actuators, B 2014, 190, 459.

[25] Cheng, T. Y.; Xu, Y. F.; Zhang, S. Y.; Zhu, W. P.; Qian, X. H.; Duan, L. P. J. Am. Chem. Soc. 2008, 130, 16160.

[26] Cheng, T. Y.; Wang, T.; Zhu, W. P.; Chen, X. L.; Yang, Y. J. Xu, Y. F.; Qian, X. H. Org. Lett. 2011, 13, 3656.

[27] Yang, Y. Y.; Cheng, T. Y.; Zhu, W. P.; Xu, Y. F.; Qian, X. H. Org. Lett. 2011, 13, 264.

[28] Dodani, S. C.; Leary, S. C.; Cobine, P. A.; Winge, D. R.; Chang, C. J. J. Am. Chem. Soc. 2011, 133, 8606.

[29] Taki, M.; Akaoka, K.; Iyoshi, S.; Yamamoto, Y. Inorg. Chem. 2012, 51, 13075.

[30] Zheng, H.; Yan, M.; Fan, X. X.; Sun, D.; Yang, S. Y.; Yang, L. J.; Li, J. D.; Jiang, Y. B. Chem. Commun. 2012, 48, 2243.

[31] Suresh, M.; Mandal, A. K.; Saha, S.; Suresh, E.; Mandoli, A.; Liddo, R. D.; Parnigotto, P. P.; Das, A. Org. Lett. 2010, 12, 5406.

[32] Mandal, A. K.; Suresh, M.; Das, P.; Suresh, E.; Mithu, B.; Ghosh, S. K.; Das, A. Org. Lett. 2012, 14, 2980.

[33] Neupane, L. N.; Park, J. Y.; Park, J. H.; Lee, K. H. Org. Lett. 2013, 15, 254.

[34] Kim, J.; Oka, Y.; Morozumi, T.; Choi, E. W.; Nakamura, H. Tetrahedron 2011, 67, 4814.

[35] Mahato, P.; Saha, S.; Suresh, E.; Liddo, R. D.; Parnigotto, P. P.; Conconi, M. T.; Kesharwani, M. K.; Ganguly, B.; Amitava, D. Inorg. Chem. 2012, 51, 1769.

[36] Chirantan, K.; Adhikari, M. D.; Ramesh, A.; Das, G. Inorg. Chem. 2013, 52, 743.

[37] Kesavapillai, S.; Clark, R. J.; Zhu, L. J. Org. Chem. 2012, 77, 8268.

[38] Chu, K. H.; Zhou, Y.; Fang, Y.; Wang, L. H.; Li, J. Y.; Yao, C. Dyes Pigm. 2013, 98, 339.

[39] Zhou, X.; Yan, W.; Zhao, T.; Tian, Z. X.; Wu, X. Tetrahedron 2013, 69, 9535.

[40] Hu, X. Y.; Zhang, X. L.; He, G. J.; He, C.; Duan, C. Y. Tetrahedron 2011, 67, 1091.

[41] Delbaere, S.; Tulyakova, E. V.; Marmois, E.; Jonusauskas, G.; Gulakova, E. N.; Fedorov, Y. V.; Fedorova, O. A. Tetrahedron 2013, 69, 8178.

[42] Fang, G.; Xu, M. Y.; Zeng, F.; Wu, S. Z. Langmuir 2010, 26, 17764.

[43] Yuan, L.; Lin, W. Y.; Chen, B.; Xie, Y. N. Org. Lett. 2012, 14, 432.

[44] Santra, M.; Roy B.; Ahn, K. H. Org. Lett. 2011, 13, 3422.

[45] Iniya, M.; Jeyanthi, D.; Krishnaveni, K.; Mahesh, A.; Chellappa, D. Spectrochim. Acta, Part A 2014, 120, 40.

[46] Goswami, S.; Das, S.; Aich, K.; Sarkar, D.; Mondal, T. K. Tetrahedron Lett. 2013, 54, 6892.

[47] Kim, M. J.; Kaur, K.; Singh, N.; Jang, D. O. Tetrahedron 2012, 68, 5429.

[48] Helal, A.; Rashid, M. H. O.; Choi, C. H.; Kim, H. S. Tetrahedron 2012, 68, 647.

[49] Chen, W. H.; Xing, Y.; Pang, Y. Org. Lett. 2011, 6, 1362.

[50] Gao, G. Y.; Qu, W. J.; Shi, B. B.; Zhang, P.; Lin, Q.; Yao, H.; Yang, W. L.; Zhang, Y. M.; Wei, T. B. Spectrochim. Acta, Part A 2014, 121, 514.

[51] Kwon, J. E.; Lee, S.; You, Y. M.; Baek, K. H.; Kei, O.; Cho, J.; Fukuzumi, S.; Shin, I.; Park, S. Y.; Nam, W. Inorg. Chem. 2012, 51, 8760.

[52] Banerjee, A.; Sahana, A.; Guha, S.; Lohar, S.; Hauli, I.; Mukhopadhyay, S. K.; Matalobos, J. S.; Debasis, D. Inorg. Chem. 2012, 51, 5699.

[53] Yang, M. H.; Thirupathi, P.; Lee, K. H. Org. Lett. 2011, 13, 5028.

[54] Zhou, Y.; Zhu, C. Y.; Gao, X. S.; You, X. Y.; Yao, C. Org. Lett. 2010, 12, 2566.

[55] Wang, F.; Nandhakumar, R.; Moon, J. H.; Kim, K. M.; Lee, J. Y.; Yoon, J. Inorg. Chem. 2011, 50, 2240.

[56] Lin, W. Y.; Yuan, L.; Feng, J. B. Eur. J. Org. Chem. 2008, 73, 3821.

[57] Zhou, Y.; Li, Z. X.; Zang, S. Q.; Zhu, Y. Y.; Zhang, H. Y.; Hou, H. W.; Thomas, C. W. M. Org. Lett. 2012, 14, 1214.

[58] Jang, S. J.; Ponnaboina, T.; Lok, N. N.; Junho, S.; Hyunsook, L.; Wan, I. L.; Lee, K. H. Org. Lett. 2012, 14, 4746.

[59] Ding, Y. B.; Li, X.; Li, T.; Zhu, W. H.; Xie, Y. S. J. Org. Chem. 2013, 78, 5328.

[60] Shen, K.; Yang, X.; Cheng, Y. X.; Zhu, C. J. Tetrahedron 2012, 68, 5719.

[61] Arturo, J. S.; Norberto, F.; Rosa, S. Tetrahedron Lett. 2013, 54, 5279.

[62] Wei, T. B.; Zhang, P.; Shi, B. B.; Chen, P.; Lin, Q.; Liu, J.; Zhang, Y. M. Dyes Pigm. 2013, 97, 297.

[63] Kumar, M.; Kumar, N.; Bhalla, V.; Singh, H.; Sharma, P. R.; Kaur, T. Org. Lett. 2011, 13, 1422.

[64] Fan, J. L; Zhan, P.; Hu, M. M.; Sun, W.; Tang, J. Z.; Wang, J. Y.; Sun, S. G.; Song, F. L.; Peng, X. J. Org. Lett. 2013, 15, 492.

[65] Lin, Q.; Liu, X.; Wei, T. B.; Zhang, Y. M. Chem. Asian J. 2013, 8, 3015.

[66] Zhang, P.; Shi, B. B.; Wei, T. B.; Zhang, Y. M.; Lin, Q.; Yao, H.; You, X. M. Dyes Pigm. 2013, 99, 857.

[67] Lin, Q.; Fu, Y. P.; Chen, P.; Wei, T. B.; Zhang, Y. M. Tetrahedron Lett. 2013, 54, 5031.

[68] Zhang, P.; Shi, B. B.; You, X. M.; Zhang, Y. M.; Lin, Q.; Yao, H.; Wei, T. B. Tetrahedron 2014, 70, 1889.

[69] Lin, Q.; Zhu, X.; Chen, P.; Fu, Y. P.; Zhang, Y. M.; Wei, T. B. Acta Chim. Sinica 2013, 71, 1516 (in Chinese).

(林奇, 朱鑫, 陈佩, 符永鹏, 张有明, 魏太保, 化学学报, 2013, 71, 1516.)

[70] Shi, B. B.; Zhang, P.; Wei, T. B.; Yao, H.; Lin, Q.; Zhang, Y. M. Chem. Commun. 2013, 49, 7812.

[71] Luo, F.; Chen, D. M.; Shi, Y. M.; Chen, X. Sci. China Chem. 2013, 43, 592 (in Chinese).

(罗峰, 陈冬梅, 施雅梅, 陈曦, 中国科学: 化学, 2013, 43, 592.)

[72] Zhang, P.; Shi, B. B.; Zhang, Y. M.; Lin, Q.; Yao, H.; You, X. M.; Wei, T. B. Tetrahedron 2013, 69, 10292.

[73] Jo, J.; Lee, H. Y.; Liu, W. J.; Olasz, A.; Chen, C. H.; Lee, D. J. Am. Chem. Soc. 2012, 134, 16000.

[74] Guo, Z. Q.; Zhu, W. H.; Zhu, M. M.; Wu, X. M.; Tian, H. Chem. Eur. J. 2010, 16, 14424.

[75] Liu, J.; Xie, Y. Q.; Lin, Q.; Shi, B. B.; Zhang, P.; Zhang, Y. M.; Wei, T. B. Sen. Actuators, B 2013, 186, 657.

[76] Shi, B. B.; Zhang, Y. M.; Wei, T. B.; Lin, Q.; Yao, H.; Zhang, P.; You, X. M. Sen. Actuators, B 2014, 190, 555.

[77] Shi, B. B.; Zhang, P.; Wei, T. B.; Yao, H.; Lin, Q.; Liu, J.; Zhang, Y. M. Tetrahedron 2013, 69, 7981.

[78] Shi, B. B.; Zhang, Y. M.; Wei, T. B.; Zhang, P.; Lin, Q.; Yao, H. New J. Chem. 2013, 37, 3737.

[79] Liu, J.; Lin, Q.; Zhang, Y. M.; Wei, T. B. Sen. Actuators, B 2014, 196, 619.

[80] Wei, T. B.; Liu, J.; Yao, H.; Xie, Y. Q.; Shi, B. B.; Zhang, P.; You, X. M.; Zhang, Y. M. Chin. J. Chem. 2013, 31, 515.

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