Application in Molecular Recognition of 1,2,3-Trizole Derivatives

doi:10.6023/cjoc201705043

Abstract

Molecular recognition is an important part of supramolecular chemistry, including cation recognition, anion recognition and neutral molecular recognition. Because of its unique structure and chemical properties, 1,2,3-trizoles is widely used in various fields of supramolecular chemistry. According to the classification of cation recognition, anion recognition, neutral molecular and biomacromolecule recognition, the applications of 1,2,3-trizole derivatives in molecular recognition are reviewed.

Key words: 1,2,3-trizoles, molecular recognition, fluorescence sensor, supramolecular chemistry

Cite this article

Xiao Liwei, Ren Ping, Jing Xuemin, Ren Lilei, Li Zheng, Dai Fucai. Application in Molecular Recognition of 1,2,3-Trizole Derivatives[J]. Chin. J. Org. Chem., 2017, 37(12): 3085-3095.

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References

[1] Fan, C.; Wu, W.; Chruma, J. J.; Zhao, J.; Yang, C. J. Am. Chem. Soc. 2016, 138, 15405
[2] Li, B.; Meng, Z.; Li, Q.; Huang, X.; Kang, Z.; Dong, H.; Chen, J.; Sun, J.; Dong, Y.; Li, J.; Jia, X.; Sessler, J. L.; Meng, Q.; Li, C. Chem. Sci. 2017, 8, 4458.
[3] Ma, J.; Meng, Q.; Hu, X.; Li, B.; Ma, S.; Hu, B.; Li, J.; Jia, X.; Li, C. Org. Lett. 2016, 18, 5740
[4] Wang, Y.; Ping, G.; Li, C. Chem. Commun. 2016, 52, 9858
[5] Wu S. Prog. Chem. 2004, 16, 175(in Chinese). (吴世康, 化学进展, 2004, 16, 175.)
[6] Martínez-Máňez, R.; Sancenón, F. Chem. Rev. 2003, 103, 4419.
[7] Lau, Y. H.; Rutledge, P. J.; Watkinson, M.; Todd, M. H. Chem. Soc. Rev. 2011, 40, 2848.
[8] Jiang, Y.; Han, C.; Liang, X.; Yang, P.; Wang, H. Chin. J. Org. Chem. 2013, 33, 1884(in Chinese). (江玉波, 韩春美, 梁雪秋, 杨朋, 王红, 有机化学, 2013, 33, 1884.)
[9] Chen, Y.; Zheng, C.; Peng, X.; Fu, Q.; Wu, L.; Lin, Q. Chin. J. Org. Chem. 2016, 36, 1779(in Chinese). (陈昱学, 郑超彭, 潇楚符, 青坛, 吴禄勇, 林强, 有机化学, 2016, 36, 1779.)
[10] Nie, J.; Li, J.-P.; Deng H.; Pan H.-C. Chin. J. Anal. Chem. 2015, 43, 609(in Chinese). (聂骥, 李建平, 邓欢, 潘宏程, 分析化学, 2015, 43, 609.)
[11] Chang, J.-J.; Wang, Y.; Zhang, H.-Z.; Zhou C.-H. Geng, R.-X.; Ji, Q.-G. Chem. J. Chin. Univ. 2011, 32, 1970(in Chinese). (常娟娟, 王艳, 张慧珍, 周成合, 耿蓉霞, 吉庆刚, 高等学校化学学报, 2011, 32,1970.)
[12] Xiao, L.; Li, L.; Gao, H.; Ren, P.; Kou, W.; Shi, Y. Chin. J. Org. Chem. 2014, 34, 2224(in Chinese). (肖立伟, 李玲玲, 高红杰, 任萍, 寇伟, 时亚如, 有机化学, 2014, 34, 2224.)
[13] Xiao, L.; Zhang, G.; Jing, X.; Zhou, Q.; Feng, R. Chin. J. Org. Chem. 2016, 36, 1000(in Chinese). (肖立伟, 张光霞, 景学敏, 周秋香, 冯茹, 有机化学, 2016, 36, 1000.)
[14] Dai, B.-N.; Cao, Q.-Y.; Wang, L.; Wang, Z. -C.; Yang, Z. Inorg. Chim. Acta 2014, 423, 163.
[15] Cao, Q.-Y.; Han, Y.-M.; Wang, H.-M.; Xie, Y. Dyes Pigm. 2013, 99, 798.
[16] Neupane, L. N.; Kim, J. M.; Lohani, C. R.; Lee, K.-H. J. Mater. Chem. 2012, 22, 4003.
[17] Singh, R. S.; Gupta, R. K.; Paitandi, R. P.; Misra, A.; Pandey, D. S. New J. Chem. 2015, 39, 2233.
[18] Vedamalai, M.; Kedaria, D.; Vasita, R.; Moric, S.; Gupta, I. Dalton Trans. 2016, 45, 2700.
[19] Ruan, Y.-B.; Maisonneuve, S.; Xie, J. Dyes Pigm. 2011, 90, 239.
[20] Lau, Y. H.; Price, J. R.; Todd, M. H.; Rutledge, P. J. Chem.-Eur. J. 2011, 17, 2850.
[21] Zhu, J.; Fan, X.; Jiang, P.; Cao, Q. Chin. J. Org. Chem. 2017, 37, 185(in Chinese). (朱江华, 范香田, 蒋平, 曹迁永, 有机化学, 2017, 37, 185.)
[22] Li, L.; Ke, C.-F.; Zhang, H.-Yi.; Liu, Y. J. Org. Chem. 2010, 75, 6673.
[23] Hung, H.-C.; Cheng, C.-W.; Wang, Y.-Y.; Chen, Y.-J.; Chung, W.-S. Eur. J. Org. Chem. 2009, 6360.
[24] Huang, X.; Meng, J.; Dong, Y.; Cheng, Y.; Zhu, C. Polymer 2010, 51, 3064.
[25] Varazo, K.; Xie, F.; Gulledge, D.; Wang, Q. Tetrahedron Lett. 2008, 49, 5293.
[26] Zhang, Y.-J.; He, X.-P.; Hu, M.; Li, Z.; Shi, X.-X.; Chen, G.-R. Dyes Pigm. 2011, 88, 391.
[27] Xu, J.; Wang, S.; Li, Y.; Zhao, H.; Li, B.; Bian, Z. Chin. J. Org. Chem. 2015, 35, 1526(in Chinese). (徐建伟, 王绍辉, 李旸, 赵海英, 李保国, 边占喜, 有机化学, 2015, 35,1526.)
[28] Qiu, S.; Xie, L.; Gao, S.; Liu, Q.; Lin, Z.; Qiu, B.; Chen, G. Anal. Chim. Acta 2011, 707, 57.
[29] Qiu, S.; Gao, S.; Zhu, X.; Lin, Z.; Qiu, B.; Chen, G. Analyst 2011, 136, 1580.
[30] Zhang, Z.; Li, W.; Zhao, Q.; Cheng, M; Xu, L.; Fang, X. Biosens. Bioelectron. 2014, 59, 40.
[31] Maity, D.; Govindaraju, T. Chem. Commun. 2010, 46, 4499.
[32] Maity, D.; Govindaraju, T. Inorg. Chem. 2010, 49, 7229.
[33] Kim, S. H.; Choi, H. S.; Kim, J.; Lee, S. J.; Quang, D. T.; Kim, J. S. Org. Lett. 2010, 12, 560.
[34] Liu, X.; Yang, X.; Peng, H.; Zhu, C.; Cheng, Y. Tetrahedron Lett. 2011, 52, 2295.
[35] Liu, X.; Yang, X.; Fu, Y.; Zhu, C.; Cheng, Y. Tetrahedron 2011, 67, 3181.
[36] Ni, X.-L.; Zeng, X.; Redshaw, C.; Yamato, T. Tetrahedron 2011, 67, 3248.
[37] Pathak, R. K.; Ibrahim, S. M.; Rao, C. P. Tetrahedron Lett. 2009, 50, 2730.
[38] Colasson, B.; Save, M.; Milko, P.; Roithova, J.; 1der, D. S.; Reinaud, O. Org. Lett. 2007, 9, 4987.
[39] Tamanini, E.; Katewa, A.; Sedger, L. M.; Todd, M. H.; Watkinson, M. Inorg. Chem. 2009, 48, 319.
[40] Tamanini, E.; Flavin, K.; Motevalli, M.; Piperno, S.; Gheber, L. A.; Todd, M. H.; Watkinson, M. Inorg. Chem. 2010, 49, 3789.
[41] Wang, Z.; Dai, B.; Qiu, J.; Cao, Q.; Ge, J. Chin. J. Org. Chem. 2015, 35, 2383(in Chinese). (王智成, 戴博娜, 丘继芳, 曹迁永, 葛金柱, 有机化学, 2015, 35, 2383.)
[42] Huang, S.; Clark, R. J.; Zhu, L. Org. Lett. 2007, 9, 4999.
[43] Kim, H.; Lee, S.; Lee, J.; Tae, J. Org. Lett. 2010, 12, 5342.
[44] Li, H.; Zheng, Q.; Han, C. Analyst 2010, 135, 1360.
[45] Zhan, J.; Wen, L.; Miao, F.; Tian, D.; Zhu, X.; Li, H. New J. Chem. 2012, 36, 656.
[46] Zhang, Y.-M.; Chen, Y.; Li, Z.-Q.; Li, N.; Liu, Y. Bioorg. Med. Chem. 2010, 18, 1415.
[47] Ast, S.; Müller, H.; Flehr, R.; Klamroth, T.; Walzb, B.; Holdt, H.-J. Chem. Commun. 2011, 47, 4685.
[48] Chang, K.-C.; Su, I.-H.; Senthilvelan, A.; Chung, W.-S. Org. Lett. 2007, 9, 3363.
[49] Maisonneuve, S.; Fang, Q.; Xie, J. Tetrahedron 2008, 64, 8716.
[50] Zhu, W.; Lü, X.; Zhu, J.; Cao, Q. Chin. J. Org. Chem. 2017, 37, 624(in Chinese). (祝文斌, 吕小兰, 朱江华, 曹迁永, 有机化学, 2017, 37, 624.)
[51] Sui, B.; Kim, B.; Zhang, Y.; Frazer, A.; Belfield, K. D. ACS Appl. Mater. Interfaces 2013, 5, 2920.
[52] Li, Y.; Flood, A. H. Angew. Chem., Int. Ed. 2008, 47, 2649.
[53] Hua, Y.; Ramabhadran, R. O.; Karty, J. A.; Raghavachari, K.; Flood, A. H. Chem. Commun. 2011, 47, 5979.
[54] Li, Y.; Pink, M.; Karty, J. A.; Flood, A. H. J. Am. Chem. Soc. 2008, 130, 17293.
[55] Zahran, E. M.; Hua, Y.; Lee, S.; Flood, A. H.; Bachas, L. G. Anal. Chem.2011, 83, 3455.
[56] Lee, S.; Hua, Y.; Park, H.; Flood, A. H. Org. Lett. 2010, 12, 2100.
[57] Mullen, K. M.; Mercurio, J.; Serpell, C. J.; Beer, P. D. Angew. Chem., Int. Ed. 2009, 48, 4781.
[58] Kilah, N. L.; Wise, M. D.; Serpell, C. J.; Thompson, A. L.; White, N. G.; Christensen, K. E.; Beer, P. D. J. Am. Chem. Soc. 2010, 132, 11893.
[59] Zheng, H.; Zhou, W.; Lv, J.; Yin, X.; Li, Y.; Liu, H.; Li, Y. Chem.-Eur. J. 2009, 15, 13253.
[60] Schulze, B.; Friebe, C.; Hager, M. D.; Günther, W.; Köhn, U.; Jahn, B. O.; Görls, H.; Schubert, U. S. Org. Lett. 2010, 12, 2710.
[61] Kumar, A.; Pandey, P. S. Org. Lett. 2008, 10, 165.
[62] Romero, T.; Caballero, A.; Tárraga, A.; Molina, P. Org. Lett. 2009, 11, 3466.
[63] Szunerits, S.; Niedziǒlka-Jönsson, J.; Boukherroub, R.; Woisel, P.; Baumann, J.-S.; Siriwardena, A. Anal. Chem. 2010, 82, 8203.
[64] Xie, D.; Li, C.; Li, S.; Qi, H.; Xue, D.; Gao, Q.; Zhang, C. Sens. Actuators B 2014,192,558.
[65] Odaci, D.; Gacal, B. N.; Gacal, B.; Timur, S.; Yagci, Y. Biomacromolecules 2009, 10, 2928.
[66] Qiu, S.; Gao, S.; Liu, Q.; Lin, Z.; Qiu, B.; Chen, G. Biosens. Bioelectron. 2011,26, 4326.
[67] Wang, T.; Shannon, C. Anal. Chim. Acta 2011, 708, 37.
[68] Bhalla, V.; Gupta, A.; Kumar, M.; Rao, D. S. S.; Prasad, S. K. ACS Appl. Mater. Interfaces 2013, 5, 672.
[69] Scavetta, E.; Mazzoni, R.; Mariani, F.; Margutta, R. G.; Bonfiglio, A.; Demelas, M.; Fiorilli, S.; Marzocchid, M.; Frabonid, B. J. Mater. Chem. B 2014, 2, 2861.
[70] Zhang, G.; Zhu, X.; Miao, F.; Tian, D.; Li, H. Org. Biomol. Chem. 2012, 10, 3185.
[71] Lu, L.; Yang, L.; Cai, H.; Zhang, L.; Lin, Z.; Guo, L.; Qiu, B.; Chen, G. Food Chem. 2014, 162, 242.
[72] Fujimoto, K.; Yamada, S.; Inouye, M. Chem. Commun. 2009, 7164.
[73] Yan, Z.; Huang, Q.; Liang, W.; Yu, X.; Zhou, D.; Wu, W.; Chruma, J. J.; Yang, C. Org. Lett. 2017, 19, 898
[74] Wang, K.-R.; An, H.-W.; Rong, R.-X.; Cao, Z.-R.; Li, X.-L. Biosens. Bioelectron. 2014, 58, 27.
[75] Dangsopon, A.; Poomsuk, N.; Siriwong, K.; Vilaivanc, T.; Suparpprom, C. RSC Adv. 2016, 6, 74314.
[76] Flaender, M.; Costa, G.; Nonglaton, G.; Saint-Pierrea, C.; Gasparutto, D. Analyst 2016, 141, 6208.

1,2,3-三唑类化合物在分子识别中的应用