Chinese Journal of Organic Chemistry >
Research Progress of Cyanide Sensors in Different Medium
Received date: 2018-10-16
Revised date: 2018-12-27
Online published: 2019-01-31
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21661028, 21662031, 21574104).
Cyanide ion has strong toxicity for mammals, because it can affect many normal function of body, such as blood vessels, visual, as well as central nervous system, heart, endocrine and metabolic system. In addition, the cyanide salts are widely used in the production of human life, especially in electroplating and plastic manufacturing, mining, gold and silver leather industry, metallurgy, etc., which resulting in the pollution of environment. Therefore, the artificial cyanide selective receptor or fluorescent sensor has attracted widely attention in the field of anionic recognition. Due to the advantages of simple synthesis method, low cost, fast response, colorimetry and/or fluorescence change before and after reaction with cyanide, chemical sensors have been deeply studied by many researchers in the past decades. Based on the reaction of cyanide ions in different media, the research progress of cyanide sensors is summarized since 2010 from four aspects:(1) identification of cyanide in pure organic phase, (2) identification of cyanide ions in aqueous media, (3) identification of cyanide ions in pure water phase, and (4) identification of cyanide ions in solid phase. These sensors for cyanide in solution and solid material test and detect cyanide by naked eyes, which realizes the convenient, fast and real-time detection of cyanide in environmental and food samples.
Qu Wenjuan , Fang Hu , Huang Qing , Zhang Youming , Lin Qi , Yao Hong , Wei Taibao . Research Progress of Cyanide Sensors in Different Medium[J]. Chinese Journal of Organic Chemistry, 2019 , 39(5) : 1226 -1243 . DOI: 10.6023/cjoc201810018
[1] Anzenbacher, J. P.; Lubal, P.; Bucek, P.; Palacios, M. A.; Kozelkova, M. E. Chem. Soc. Rev. 2010, 39, 3954.
[2] Gale, P. A.; Garcia-Garrido, S. E.; Garric, J. Chem. Soc. Rev. 2008, 37, 151.
[3] Lemos, S. G.; Nogueira, A. R. A.; Torre-Neto, A. Parra A.; Alonso, J. J. Agric. Food. Chem. 2007, 55, 4658.
[4] Wang, Q.; Xie, Y.; Ding, Y. Li, X.; Zhu, W. Chem. Commun. 2010, 46, 3669.
[5] 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.)
[6] Qu, W. J.; Li, W. T.; Zhang, H. L.; Zhang, Y. M.; Lin, Q.; Yao, H.; Wei, T. B. Chin. J. Org. Chem. 2018, 38, 1792(in Chinese). (曲文娟, 李文婷, 张海丽, 张有明, 林奇, 姚虹, 魏太保, 有机化学, 2018, 38, 1792.)
[7] Li, W. T.; Qu, W. J.; Zhang, H. L.; Li, X.; Lin, Q.; Yao, H.; Zhang, Y. M.; Wei, T. B. Chin. J. Org. Chem. 2017, 37, 2619(in Chinese). (李文婷, 曲文娟, 张海丽, 李翔, 林奇, 姚虹, 张有明, 魏太保, 有机化学, 2017, 37, 2619.)
[8] Xu, Z.; Chen, X.; Kim, H. N.; Yoon, J. Chem. Soc. Rev. 2010, 39, 127.
[9] Sen, B.; Mukherjee, M.; Pal, S.; Mandal, S. K.; Hundal, M. S.; Khuda-Bukhshb, A. R.; Chattopadhyay, P. RSC Adv. 2014, 4, 15356.
[10] Li, Q.; Guo, Y.; Shao, S. Analyst 2012, 137, 4497.
[11] Li, Q.; Yue, Y.; Guo, Y.; Shao, S. Sens. Actuators, B 2012, 173, 797.
[12] Vennesland, B.; Conn, E. E.; Knowles, C. J.; Westley, J.; Wissing, F. Cyanide in Biology, Academic Press, London, 1981.
[13] Way, J. L. Annu. Rev. Pharmacol. Toxicol. 1984, 24, 451.
[14] Anderson, R.; Harland, W. Med., Sci. Law 1982, 22, 35.
[15] Becker, C. Vet. Hum. Toxicol. 1985, 27, 487.
[16] Zamecnik, J.; Tam, J. J. Anal. Toxicol. 1987, 11, 47.
[17] Levin, B. C.; Cabrera, F. M.; Landron, F.; Clark, H. M.; Rodriguez, J. R.; Gurman, J. L.; Droz, L.; Yoklavich, M. F.; Rechani, P. R; Kaye, S. J. Forensic Sci. 1990, 35, 151.
[18] Matsubara, K.; Akane, A.; Maseda, C.; Shiono, H. Forensic Sci. Int. 1990, 46, 203.
[19] Mayes, R. W. J. Forensic Sci. 1991, 36, 179.
[20] Baird, C.; Cann, M. Macmillan 2005.
[21] Selkoe, D. J.; Schenk, D. Annu. Rev. Pharmacol. Toxicol. 2003, 43, 545.
[22] Young, C.; Tidwel, L. Cyanide:Social, Industrial and Economic Aspects: Minerals, Metals, and Materials Society, Anderson, C., Warrendale, PA, 2001.
[23] Keshava, K.; Torawaneb, P.; Kumawatd, M. K.; Tayadeb, K.; Sahooc, S. K.; Srivastavad, R.; Kuwarb, A. Biosens. Bioelectron. 2017, 92, 95.
[24] Noh, J. Y.; Hwang, I. H.; Kim, H.; Song, E. J.; Kim, K. B.; Kim, C. Bull. Korean Chem. Soc. 2013, 34, 1985.
[25] Park, G. J.; Hwang, I. H.; Song, E. J.; Kim, H.; Kim, C. Tetrahedron 2014, 70, 2822.
[26] Tang, L.; Zhou, P.; Zhong, K.; Hou, S. Sens. Actuators, B. 2013, 182, 439.
[27] Chen, X.; Nam, S. W.; Kim, G. H.; Song, N.; Jeong, Y.; Shin, I.; Kim, S. K.; Kim, J.; Park, S.; Yoon, J. Chem. Commun. 2010, 46, 8953.
[28] Qu, Y.; Jin, B.; Liu, Y.; Wu, Y.; Yang, L.; Wu, J.; Hua, J. Tetrahedron Lett. 2013, 54, 4942.
[29] Goswami, S.; Manna, A.; Paul, S.; Das, A. K.; Aich, K.; Nandi, P. K. Chem. Commun. 2013, 49, 2912.
[30] Lee, S. A.; You, G. R.; Choi, Y. W.; Jo, H. Y.; Kim, A. R.; Noh, I.; Kim, S. J.; Kim, Y.; Kim, C. Dalton Trans. 2014, 43, 6650.
[31] Lee, S. A.; You, G. R.; Choi, Y. W.; Jo, H. Y.; Kim, A. R.; Noh, I.; Kim, S. J.; Kim, Y.; Kim, C. Dalton Trans. 2014, 43, 6650.
[32] Jones, D. A. Phytochemistry 1998, 47, 15.
[33] Greenfield, R. A.; Brown, B. R.; Hutchins, J. B.; Iandolo, J. J.; Jackson, R.; Slater, L. N.; Bronze, M. S. Am. J. Med. Sci. 2002, 323, 326.
[34] Guidelines for Drinking-Water Quality. World Health Organization, Geneva, 1996.
[35] Sun, S. S.; Lees, A. J. Chem. Commun. 2000, 17, 1687.
[36] Miyaji, H.; Sessler, J. L. Angew. Chem. 2001, 113, 158.
[37] Kim, Y.; Zhao, Y.; Gabbaï, F. P. Angew. Chem., Int. Ed. 2009, 48, 4957.
[38] Anzenbacher, P.; Tyson, D. S.; Jursíkova, K.; Castellano, F. N. J. Am. Chem. Soc. 2002, 124, 6232.
[39] Shang, L.; Jin, L.; Dong, S. Chem. Commun. 2009, 21, 3077.
[40] Senapati, D.; Dasary, S. S.; Singh, A. K.; Senapati, T.; Yu, H.; Ray, P. C. Chem.-Eur. J. 2011, 17, 8445.
[41] Gimeno, N.; Li, X.; Durrant, J. R.; Vilar, R. Chem.-Eur. J. 2008, 14, 3006.
[42] Xu, Z.; Pan, J.; Spring, D. R.; Cui, J.; Yoon, J. Tetrahedron 2010, 66, 1678.
[43] Cheng, X.; Tang, R.; Jia, H.; Feng, J.; Qin, J.; Li, Z. ACS Appl. Mater. Interfaces 2012, 4, 4387.
[44] Cho, D. G.; Sessler, J. L. Chem. Soc. Rev. 2009, 38, 1647.
[45] Afkhami, A.; Sarlak, N. Sens. Actuators, B 2007, 122, 437.
[46] Badugu, R.; Lakowicz, J. R.; Geddes, C. D. J. Am. Chem. Soc. 2005, 127, 3635.
[47] Wu, Y.; Wang, J.; Zeng, F.; Huang, S.; Huang, J.; Xie, H.; Yu, C.; Wu, S. ACS Appl. Mater. Interfaces 2016, 8, 1511.
[48] Kumari, N.; Jha, S.; Bhattacharya, S. J. Org. Chem. 2011, 76, 8215.
[49] Zhou, X.; Lv, X.; Hao, J.; Liu, D.; Guo, W. Dyes Pigm. 2012, 95, 168.
[50] Dong, M.; Peng, Y.; Dong, Y. M.; Tang, N.; Wang, Y. W. Org. Lett. 2012, 14, 130.
[51] Khatua, S.; Samanta, D.; Bats, J. W.; Schmittel, M. Inorg. Chem. 2012, 51, 7075.
[52] Fillaut, J. L.; Akdas-Kilig, H.; Dean, E.; Latouche, C.; Boucekkine, A. Inorg. Chem. 2013, 52, 4890.
[53] Kang, J.; Song, E. J.; Kim, H.; Kim, Y. H.; Kim, Y.; Kim, S. J.; C. Kim, Tetrahedron Lett. 2013, 54, 1015.
[54] Yang, L.; Li, X.; Yang, J.; Qu, Y.; Hua, J. ACS Appl. Mater. Interfaces 2013, 5, 1317.
[55] Yang, Y.; Yin, C.; Huo, F.; Chao, J.; Zhang, Y.; Cheng, F. Sens. Actuators, B 2014, 193, 220.
[56] Liu, Y. W.; Kao, M. X.; Wu, A. T. Sens. Actuators, B 2015, 208, 429.
[57] Xing, P.; Xu, Y.; Li, H.; Liu, S.; Lu, A.; Sun, S. Sci Rep. 2015, 5, 16528.
[58] Bejoymohandas, K. S.; Kumar, A.; Sreenadh, S.; Varathan, E.; Varughese, S.; Subramanian, V.; Reddy, M. L. P. Inorg. Chem. 2016, 55, 3448.
[59] Volpi, G. J. Chem. Educ. 2016, 93, 891.
[60] Wu, H.; Chen, Y.; Rao, C.; Fan, D.; Wei, H.; Liu, C. Tetrahedron Lett. 2016, 57, 4969.
[61] Wang, L.; Zhu, L.; Li, L.; Cao, D. RSC Adv. 2016, 6, 55182.
[62] Huo, F.; Zhang, Y.; Yue, Y.; Chao, J.; Zhang, Y.; Yin, C. Dyes Pigm. 2017, 143, 270.
[63] Liu, J.; Liu, Y.; Liu, Q.; Li, C.; Sun, L.; Li, F. J. Am. Chem. Soc. 2011, 133, 15276.
[64] Lee, H.; Kim, H. J. Tetrahedron Lett. 2012, 53, 5455.
[65] Jo, J.; Olasz, A.; Chen, C. H.; Lee, D. J. Am. Chem. Soc. 2013, 135, 3620.
[66] Robbins, T. F.; Qian, H.; Su, X.; Hughes, R. P.; Aprahamian, I. Org. Lett. 2013, 15, 2386.
[67] Lin, W. C.; Fang, S. K.; Hu, J. W.; Tsai, H. Y.; Chen, K. Y. Anal. Chem. 2014, 86, 4648.
[68] Pramanik, S.; Bhalla, V.; Kumar, M. ACS Appl. Mater. Interfaces 2014, 6, 5930.
[69] Qu, W.; Gao, G.; Shi, B.; Zhang, P.; Wei, T.; Lin, Q.; Yao, H.; Zhang, Y. Supramol. Chem. 2014, 26, 403.
[70] Qu, W.; Gao, G.; Shi, B.; Zhang, P.; Wei, T.; Lin, Q.; Yao, H.; Zhang, Y. Supramol. Chem. 2014, 26, 403.
[71] Chen, K. Y.; Lin, W. C. Dyes Pigm. 2015, 123, 1.
[72] Qiao, L.; Cai, Y.; Yao, H.; Lin, Q.; Zhu, Y. R.; Li, H.; Zhang, Y. M.; Wei, T. B. Spectrochim. Acta., Part A 2015, 136, 1047.
[73] Chow, C. F.; Ho, P. Y.; Wong, W. L.; Gong, C. B. Chem.-Eur. J. 2015, 21, 12984.
[74] Cheng, X.; Li, H.; Zheng, F.; Lin, Q.; Zhang, Y.; Yao, H.; Wei, T. Dyes Pigm. 2016, 127, 59.
[75] Jeong, J. W.; Angupillai, S.; Kim, I. J.; Jeonga, J.; Kim, H. S.; So, H. S.; Son, Y. A. Sens. Actuators, B 2016, 237, 341.
[76] Singh, Y.; Ghosh, T. Talanta 2016, 148, 257.
[77] Wei, T. B.; Li, W. T.; Li, Q.; Qu, W. J.; Li, H.; Yan, G. T.; Lin, Q.; Yao, H.; Zhang, Y. M. RSC Adv. 2016, 6, 43832.
[78] El-Shishtawy, R. M.; Al-Zahrani, F. A. M.; Al-amshany, Z. M.; Asiri, A. M. Sens. Actuators, B 2017, 240, 288.
[79] Wang, L.; Li, L.; Cao, D. Sens. Actuators, B 2017, 241, 1224.
[80] Liu, T.; Huo, F.; Li, J.; Cheng, F.; Yin, C. Sens. Actuators, B 2017, 239, 526.
[81] Chen, J.; Li, W.; Li, Q.; Lin, Q.; Yao, H.; Zhang, Y.; Wei, T. Chin. J. Chem. 2017, 35, 1165.
[82] Shiraishi, Y.; Sumiya, S.; Manabe, K.; Hirai, T. ACS Appl. Mater. Interfaces 2011, 3, 4649.
[83] Lin, Q.; Liu, X.; Wei, T. B.; Zhang, Y. M. Chem. Asian J. 2013, 8, 3015.
[84] Wang, P.; Yao, Y.; Xue, M. Chem. Commun. 2014, 50, 5064.
[85] Rhaman, M. M.; Alamgir, A.; Wong, B. M.; Powell, D. R.; Hossain, M. A. RSC Adv. 2014, 4, 54263.
[86] Jung, K.; Lee, H. Anal. Chem. 2015, 87, 9308.
[87] Qing, Z.; Hou, L.; Yang, L.; Zhu, L.; Yang, S.; Zheng, J.; Yang, R. Anal. Chem. 2016, 88, 9759.
[88] Bhowmick, I.; Boston, D. J.; Higgins, R. F.; Klug, C. M.; Shores, M. P.; Gupta, T. Sens. Actuators, B 2016, 235, 325.
[89] Wei, T. B.; Li, W. T.; Li, Q.; Su, J. X.; Qu, W. J.; Lin, Q.; Yao, H.; Zhang, Y. M. Tetrahedron Lett. 2016, 57, 2767.
[90] Li, Y.; Wang, Q.; Zhou, X.; Wen, C.; Yu, J.; Han, X.; Li, X.; Yan, Z.; Zeng, J. Sens. Actuators, B 2016, 228, 366.
[91] Uppa, S. H.; Tripathy, S.; Chawla, S.; Sharma, B.; Dalai, M. K.; Singh, S. P.; Singh, S.; Singh, N. J. Environ. Sci. 2017, 55, 76.
[92] Lin, Q.; Liu, L.; Zheng, F.; Mao, P. P.; Liu, J.; Zhang, Y. M.; Yao, H.; Wei, T. B. Tetrahedron 2017, 73, 5307.
[93] Momeni, S.; Ahmadi, R.; Safavi, A.; Nabipour, I. Talanta 2017, 175, 514.
[94] Männel-Croisé, C.; Zelder, F. ACS Appl. Mater. Interfaces 2012, 4, 725.
[95] Zong, C.; Zheng, L. R.; He, W.; Ren, X.; Jiang, C.; Lu, L. Anal. Chem. 2014, 86, 1687.
[96] Lin, Q.; Lu, T. T.; Zhu, X.; Sun, B.; Yang, Q. P.; Wei, T. B.; Zhang, Y. M. Chem. Commun. 2015, 51, 1635.
[97] Barare, B.; Babahan, I.; Hijji, Y. M.; Bonyi, E.; Tadesse, S.; Aslan, K. Sensors 2016, 16, 271.
[98] Incel, A.; Akin, O.; Cagir, A.; Yildiz, Ü. H.; Demir, M. M. Sens. Actuators, B 2017, 252, 886.
[99] Kim, M. J.; Manivannan, R.; Kim, I. J.; Son, Y. A. Sens. Actuators, B 2017, 253, 942.
[100] Maurya, N.; Singh, A. K. Sens. Actuators, B 2017, 245, 74.
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