Chinese Journal of Organic Chemistry >
Progress in Fluorescent Chemosensors for Chiral Enantiomer Recognition Based on 2,2’-Naphthol Derivatives
Received date: 2013-06-09
Revised date: 2013-07-24
Online published: 2013-08-16
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 20872027, 90913001) and the Technological Project of Henan Province (Nos. 132102210388, 132300410055).
Being an axial chiral compound with optical activity, 2,2'-naphthol (BINOL) has become one of the basic units for constructing various chiral fluorescent chemosensors in recent years. According to the literatures, chiral BINOL derivatives chemosensors carry out highly enantioselective, sensitive recognition of amino acid and its derivatives, chiral amino alcohols, and α-hydroxycarboxylic acids. In this progress, BINOL derivatives as enantioselective chemosensors for chiral enantiomers are summarized.
Key words： chiral enantiomer; 2,2’-naphthol; chemosensor; fluorescence
Yang Li , Xu Kuoxi , Wang Chenjuan , Wang Chaojie . Progress in Fluorescent Chemosensors for Chiral Enantiomer Recognition Based on 2,2’-Naphthol Derivatives[J]. Chinese Journal of Organic Chemistry, 2013 , 33(12) : 2496 -2503 . DOI: 10.6023/cjoc201306015
[1] Lucey, J. F.; Behrman, R. B. Science 1963, 139, 1295.
[2] Cheng, P.-F.; Jiao, S.-Y.; Xu, K.-X.; Wang, C.-J. Chin. J. Org. Chem. 2013, 33, 280 (in Chinese). (程鹏飞, 焦书燕, 徐括喜, 王超杰, 有机化学, 2013, 33, 280.)
[3] Huang H.; Zheng, L.-F.; Zou, X.-W.; Cheng, Y.-X. Prog. Chem. 2008, 20, 508 (in Chinese). (黄辉, 郑立飞, 邹小伟, 成义祥, 化学进展, 2008, 20, 508.)
[4] Xu, K.-X.; He, Y.-B.; Qin, H.-J.; Qing, G.-Y.; Liu, S.-Y. Tetrahedron: Asymmetry 2005, 16, 3042.
[5] Johnson, K. S,; Needoba, J. A.; Riser, S. C.; Showers, W. J. Chem. Rev. 2007, 107, 623.
[6] McDonagh, C.; Burke, C.-S.; MacCraith, B. D. Chem. Rev. 2008, 108, 400.
[7] Borisov, S.-M.; Wolfbeis, O. S. Chem. Rev. 2008, 108, 423.
[8] Lee, D. H.; Lee, H. Y.; Lee, K. H. Chem. Commun. 2001, 1188.
[9] Hennrich, G.; Sonnenschein, H.; Resch-Genger, U. Tetrahedron Lett. 2001, 42, 2805.
[10] Xu, K.-X.; Qiu, Z.; Zhao, J.-J.; Zhao, J.; Wang, C.-J. Tetrahedron: Asymmetry 2009, 20, 1690.
[11] Xu, K.-X.; Yang, L.-R.; Wang, Y.-X.; Zhao, J.; Wang, C.-J. Supramol. Chem. 2010, 22, 563.
[12] Lu, Q.-S.; Dong, L.; Qin, S.; Hu, C.-W.; Yu, X.-Q. Org. Lett. 2009, 669.
[13] Hu, C.-G.; Huang, X.-H.; Chen, Z.-H.; He, Y.-B. Chin. J. Chem. 2009, 27, 157.
[14] He, X.; Cui, X.; Li, M.; Lin, L.; Feng, X.-M. Tetrahedron Lett. 2009, 50, 5853
[15] Xu, K.-X.; Bu, Z.-W.; Huang, K.-J.; Zhao, J.; Wang, C.-J. Chin. J. Chem. 2010, 28, 803.
[16] Xu, K.-X.; Wang, Y.-X.; Jiao, S.-Y.; Zhao, J.; Wang, C.-J. Can. J. Chem. 2010, 88, 367.
[17] Xu, K.-X.; Cheng, P.-F.; Zhao, J.; Wang, C.-J. J. Fluoresc. 2011, 21, 991.
[18] Tang, L.; Wei, G.; Nandhakumar, R. Bull. Korean Chem. Soc. 2011, 9, 3367.
[19] Boiocchi, M.; Bonizzoni, M.; Fabbrizzi, L. Angew. Chem., Int. Ed., 2004, 43, 3847.
[20] Bonizzoni, M.; Fabbrizzi, L.; Piovani, G. Tetrahedron 2004, 60, 11159.
[21] Raker, J.; Glasss, T. E. J. Org. Chem. 2002, 67, 6113.
[22] Sancenón, F.; Martínez-Máñez, R.; Miranda, M. A. Angew. Chem., Int. Ed. 2003, 42, 647.
[23] Kim, S. K.; Kang, B. G.; Koh, H. S. Org. Lett. 2004, 6, 4655.
[24] Fabbrizzi, L.; Foti, F.; Tagletti, A. Org. Lett. 2005, 7, 2603.
[25] Kruppa M.; König, B. Chem. Rev. 2006, 106, 3520.
[26] Yang, X.; Liu, X.; Shen, K.; Zhu, C.; Cheng, Y. Org. Lett. 2011, 13, 3510.
[27] Huang, H.; Nandhakumar, R.; Cho, M.; Su, Z.; Kim, K. M. J. Am. Chem. Soc. 2013, 135, 2653.
[28] Song, F.; Fei, N.; Li, F.; Zhang, S.; Cheng, Y.; Zhu, C. Chem. Commun. 2013, 49, 2891.
[29] Xu, K.-X.; Jiao, S.-Y.; Yao, W.-Y.; Xie, E.; Tang, B.-W.; Wang, C.-J. Chirality 2012, 24, 646.
[30] Wang. Q.; Chen, X.; Tao, L.; Wang, L.; Xiao, D.; Yu, X.-Q.; Pu, L. J. Org. Chem. 2007, 72, 97.
[31] Nandhakumar, R.; Ryu, J.; Park, H.; Tang, L.; Choi, S.; Kim, K. M. Tetrahedron 2008, 64, 7704.
[32] Nandhakumar, R.; Soo, A. Y.; Hong, J.; Hamb, S.; Kima, K. M. Tetrahedron 2009, 65, 666.
[33] Chen, X.; Huang, Z.; Chen, S.-Y.; Li, K.; Yu, X.-Q.; Pu, L. J. Am. Chem. Soc. 2010, 132, 7297.
[34] Jiao, J.; Liu, X.; Mao, X.; Li, J.; Cheng, Y.; Zhu, C. New J. Chem. 2013, 37, 317.
[35] Yu, S.; Pu, L. J. Am. Chem. Soc. 2010, 132, 17698.
[36] Yu, S.; Plunkett, W.; Kim, M.; Pu, L. J. Am. Chem. Soc. 2012, 134, 20282.
[37] Shi, J.-H.; Cheng, X.-W.; Yan, W. Chin. J. Pharm. Anal. 2009, 29, 1681 (in Chinese). (施介华, 程向炜, 严巍, 药物分析杂志, 2009, 29, 1681.)
[38] Xu, K.-X.; Wu, X.-J.; He, Y.-B.; Liu, S.-Y.; Qing, G.-Y.; Meng, L.-Z. Tetrahedron: Asymmetry 2005, 16, 833.
[39] Xu, G.-Y.; Li, M.-H.; Liu, L.-L. Pharmaceutical Intermediate Manual, Chemical Industry Press, Beijing, 2000, p. 164 (in Chinese). (许关煜, 李敏华, 刘玲玲, 医药中间体手册, 化学工业出版社, 北京, 2000, p. 164.)
[40] Liu, H.-L.; Hou, X.-L.; Pu, L. Angew. Chem., Int. Ed. 2009, 48, 382.
[41] Shirakawa, S.; Moriyama, A.; Shimizu, S. Eur. J. Org. Chem. 2008, 5957.
[42] Heo, J.; Mirkin, C. A. Angew. Chem., Int. Ed. 2006, 45, 941.
[43] Li. Z.-B.; Lin, J.; Sabat, M.; Hyacinth, M.; Pu, L. J. Org. Chem. 2007, 72, 4905.
[44] Xu, K.-X.; Chen, P.-F.; Wang, Y.-X.; Zhao, J.; Wang, C.-J. Supramol. Chem. 2009, 21, 618.
[45] Liu, H.-L.; Hou, X.-L.; Pu, L. Angew. Chem., Int. Ed. 2009, 48, 382.
[46] Liu, H.-L.; Peng, Q.; Wu, Y.-D.; Chen, D.; Wu, Y.-D.; Hou, X.-L.; Sabat, M.; Pu, L. Angew. Chem., Int. Ed. 2010, 49, 602.
[47] Yang, X.; Liu, X.; Shen, K.; Fu, Y.; Zhang, M.; Zhu, C.-J.; Cheng, Y.-X. Org. Biomol. Chem. 2011, 9, 6011.
[48] Xu, K.-X.; Jiao, S.-Y.; Yao, W.-Y.; Kong, H.-J.; Zhang, J.-L.; Wang, C.-J. Sens. Actuators, B 2013, 177, 384.
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