Synthesis of a Novel Benzothiazole-Rhodamine Derivative and Its Selective Detection of Fe3+, Al3+ and Cr3+

doi:10.6023/cjoc201512041

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (4): 768-773.DOI: 10.6023/cjoc201512041 Previous Articles Next Articles

ARTICLE

一种苯并噻唑-罗丹明衍生物的合成及其对Fe³⁺、Al³⁺、Cr³⁺的识别

侯淑华, 曲忠国, 钟克利, 边延江, 汤立军

渤海大学化学化工学院锦州 121013

收稿日期:2015-12-26 修回日期:2016-02-02 发布日期:2016-02-24
通讯作者: 汤立军 E-mail:bhutang@126.com
基金资助:
辽宁省高等学校优秀人才支持计划(No.LR2015001)资助项目.

Synthesis of a Novel Benzothiazole-Rhodamine Derivative and Its Selective Detection of Fe³⁺, Al³⁺ and Cr³⁺

Hou Shuhua, Qu Zhongguo, Zhong Keli, Bian Yanjiang, Tang Lijun

Department of Chemistry, Bohai University, Jinzhou 121013

Received:2015-12-26 Revised:2016-02-02 Published:2016-02-24
Supported by:
Project supported by the Liaoning Excellent Talents in University (No. LR2015001).

1. Synthesis of a Novel Benzothiazole-Rhodamine Derivative and Its Selective Detection of Fe³⁺, Al³⁺ and Cr³⁺.PDF(978KB)

Abstract

A novel rhodamine-based probe L was synthesized from rhodamine B through "click chemistry". It showed that probe L acted as a naked-eye and "turn on" fluorescent probe for Fe³⁺, Al³⁺ and Cr³⁺ recognition.L is highly selective to trivalent ions (Fe³⁺, Al³⁺ and Cr³⁺) over other monovalent or divalent ions in CH₃OH. Detection limits of probe L for Fe³⁺, Cr³⁺and Al³⁺ are 9.7×10^-5, 6.9×10^-5 and 1.4×10^-4 mol/L, respectively, which could make it potentially applicable in Fe³⁺, Cr³⁺ and Al³⁺ detection.

Key words: rhodamine, benzothiazole, click chemistry

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Hou Shuhua, Qu Zhongguo, Zhong Keli, Bian Yanjiang, Tang Lijun. Synthesis of a Novel Benzothiazole-Rhodamine Derivative and Its Selective Detection of Fe³⁺, Al³⁺ and Cr³⁺[J]. Chin. J. Org. Chem., 2016, 36(4): 768-773.

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[1] Aisen, P.; Wessling-Resnick, M.; Leibold, E. A. Curr. Opin. Chem. Biol. 1999, 3, 200.
[2] (a) Pithadia, A. S.; Lim, M. H. Curr. Opin. Chem. Biol. 2012, 16, 67.
(b) Weizman, H.; Ardon, O.; Mester, B.; Libman, J.; Dwir, O.; Hadar, Y.; Chen, Y.; Shanzer, A. J. Am. Chem. Soc. 1996, 118, 12368.
(c) Touati, D. Arch. Biochem. Biophys. 2000, 373, 1.
[3] Singh, A. K.; Gupta, V.; Gupta, B. Anal. Chim. Acta 2007, 585, 171.
[4] Vincent J B. Nutr. Rev. 2000, 58(3): 67.
[5] (a) Perl, D. P.; Gajdusek, D. C.; Garruto, R. M.; Yanagihara, R. T.; Gibbs, C. J. Science 1982, 217, 1053.
(b) Crapper, D.; Krishnan, S.; Dalton, A. Science 1973, 180, 511.
[6] (a) Zhu, L.; Younes, A. H.; Zhao Y.; Clark, R. J. J. Photochem. Photobiol. A Chem. 2015, 311, 1.
(b) Li, H.; Fan, J.; Peng, X. Chem. Soc. Rev. 2013, 42, 7943.
(c) Zhu, L.; Zhao, Y.; Simmons, J.; Sreenath, K. RSC Adv. 2014, 4, 20398.
(d) Yin, J.; Hu, Y.; Yoon, J. Chem. Soc. Rev. 2015, 44, 4619.
(e) Zhao, Y.; Younes, A.; Allen, J.; Davidson, M.; Zhu, L. J. Org. Chem. 2015, 80, 5600.
(f) Sreenath, K.; Zhao, Y.; Allen, J.; Davidson, M.; Zhu, L. Chem. Eur. J. 2015, 21, 867.
(g) Simmons, J.; Zhao, Y.; Daykin, K.; Nguyen, B.; Clark, R.; Shatruk, M.; Zhu, L. Supramol. Chem. 2014, 26, 214.
[7] (a) Ng, S. M.; Narayanaswamy, R. Anal. Bioanal. Chem. 2006, 386, 1235.
(b) Lv, Y.; Zhu, L.; Liu, H.; Wu, Y.; Chen, Z.; Fu, H.; Tian, Z. Anal. Chim. Acta 2014, 839, 74.
(c) Zhan, S.; Xu, H.; Zhang, D.; Xia, B.; Zhan, X.; Wang, L.; Lv, J.; Zhou, P. Biosens. Bioelectron. 2015, 72, 95.
(d) Maiti, S.; Aydin, Z.; Zhang, Y.; Guo, M. Dalton Trans. 2015, 44, 8942.
(e) Wang, M.; Wang, F.; Wang, Y.; Zhang, W.; Chen, X. Dyes Pigm. 2015, 120, 307.
(f) Prabhu, J.; Velmurugan, K.; Nandhakumar, R. J. Anal. Chem. 2015, 70, 943.
(g) Antony, E. J.; Raj, M.; Paulpandi, R. Q.; Paulraj, M. S.; Enoch, I. V. M. V. J. Fluoresc. 2015, 25, 1031.
(h) Geng, T.-M.; Wu, D.-Y.; Huang, W.; Huang, R.-Y.; Wu, G.-H. J. Polym. Res. 2014, 21, 354.
(i) Xu, Z.; Baek, K.-H.; Kim, H. N.; Cui, J.; Qian, X.; Spring, D. R.; Shin, I.; Yoon, J. J. Am. Chem. Soc. 2009, 132, 601.
(j) Azadbakht, R.; Vaisi, H.; Mohamadvand, H.; Khanabadi, J. Spectrochim. Acta A 2015, 145, 575.
[8] Mao, J.; Wang, L.; Dou, W.; Tang, X.; Yan, Y.; Liu, W. Org. lett. 2007, 9, 4567.
[9] Li, Z.; Hu, Q.; Li, C.; Dou, J.; Cao, J.; Chen, W.; Zhu, Q. Tetrahedron Lett. 2014, 55, 1258.
[10] (a) Ding, Y.; Tang, Y.; Zhu, W.; Xie, Y. Chem. Soc. Rev. 2015, 44(5), 1101.
(b) Xie, Y.; Wei, P.; Li, X.; Hong, T.; Zhang, K.; Furuta, H. J. Am. Chem. Soc. 2013, 135(51), 19119.
(c) Chen, B.; Ding, Y.; Li, X.; Zhu, W.; Hill, J.; Ariga, K.; Xie, Y. Chem. Commun. 2013, 49(86), 10136.
(d) Ding, Y.; Li, X.; Li, Tong.; Zhu, W.; Xie, Y. J. Org. Chem. 2013, 78(11), 5328.
(e) Xie, Y.; Ding, Y.; Li, X.; Wang, C.; Hill, J.; Ariga, K.; Wang, W.; Zhu, W. Chem. Comm. 2012, 48(94), 11513.
[11] Chereddy, N. R.; Nagaraju, P.; Raju, M. V.; Krishnaswamy, V. R.; Korrapati, P. S.; Bangal, P. R.; Rao, V. J. Biosens. Bioelectron. 2015, 68, 749.
[12] (a) Fang, F.-L.; Jing, J. Q.; Chen, X. M. Chin. J. Org. Chem. 2014, 34, 2178 (in Chinese). (范方禄, 靖金球, 陈雪梅, 有机化学, 2014, 34, 2178.)
[13] Tang, L.; Dai, X.; Wen, X.; Wu, D.; Zhang, Q. Spectrochim. Acta A 2015, 139, 329.
[14] Majumdar, P.; Zhao, J. J. Phys. Chem. B 2015, 119(6), 2384.
[15] (a) Ingale, S. A.; Seela, F. J. J. Org. Chem. 2013, 78, 3394.
(b)Yuan, Z.; Kuang, G. C.; Clark, R. J.; Zhu, L. Org. Lett. 2012, 14, 2590.
(c) Bevilacqua, V.; King, M.; Chaumontet, M.; Nothisen, M.; Gabillet, S.; Buisson, D.; Puente, C.; Wagner, A.; Taran, F. Angew. Chem. Int. Ed. 2014, 53, 5872.
(d) Yuan, Z.; Liang, F. Curr. Org. Chem. 2014, 18, 2016.
[16] Srinivas, A. S. US 20070088043, 2007 [Chem. Abstr. 2007, 146, 441825].
[17] Zhang, X.; He, Y.; Yu, Z.; Jiang, Z.; Yang, Z.; Dong, Y.; Nabinger, S.; Zhang, Z. J. Med. Chem. 2010, 53, 2482.
[18] Yapici, N.; Mandalapu, S.; Chew, T.; Khuon, S.; Bi, L. Bioorg. Med. Chem. Lett. 2012, 22, 2440.

一种苯并噻唑-罗丹明衍生物的合成及其对Fe³⁺、Al³⁺、Cr³⁺的识别

Synthesis of a Novel Benzothiazole-Rhodamine Derivative and Its Selective Detection of Fe³⁺, Al³⁺ and Cr³⁺

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一种苯并噻唑-罗丹明衍生物的合成及其对Fe3+、Al3+、Cr3+的识别