Chinese Journal of Organic Chemistry >
Synthesis, Recognition and Sensing Properties for Anions Based on a Carbazole Derivative Containing Phenylaminothiourea Units
Received date: 2014-10-22
Revised date: 2014-12-10
Online published: 2015-01-06
Supported by
Project supported by the National Natural Science Foundation of China (No.21161005).
A carbazole-based anion receptor (L) containing phenylaminothiourea recognition units was designed and synthesized using carbazole as starting compound, and its structure was characterized by 1H NMR, 13C NMR, MS, IR and elemental analysis. UV-Vis and fluorescence titration experiments indicated that L selectively recognized F-, AcO- and H2PO4- in DMSO, showing strong interactions (Ka>104 L/mol) with these three anions. During the anion recognition process, a naked-eye de-tectable color change and a distinct fluorescence quenching of L were simultaneously observed, indicative of its potential as colorimetric and fluorescent sensors for anions. Interestingly, only F- and AcO- could be recognized by L in DMSO containing 10% (V/V) H2O; a specific recognition of L towards AcO- was realized in DMSO containing 20% (V/V) H2O.
Key words： phenylaminothiourea; carbazole; hydrogen bond; anion recognition; sensing
Jian Junyou, Yan Boren, Pan Dingwu, Tan Zan, Lü Xinyang, Du Huan, Bao Xiaoping . Synthesis, Recognition and Sensing Properties for Anions Based on a Carbazole Derivative Containing Phenylaminothiourea Units[J]. Chinese Journal of Organic Chemistry, 2015 , 35(5) : 1069 -1074 . DOI: 10.6023/cjoc201410030
[1] Gale, P. A. Chem. Soc. Rev. 2010, 39, 3746.
[2] Bondy, C. R.; Loeb, S. J. Coord. Chem. Rev. 2003, 240, 77.
[3] Beer, P. D.; Gale, P. A. Angew. Chem., Int. Ed. 2001, 40, 486.
[4] Zhou, Y.; Zhang, J. F.; Yoon, J. Chem. Rev. 2014, 114, 5511
[5] Pandurangan, K.; Kitchen, J. A.; Gunnlaugsson, T. Tetrahedron Lett. 2013, 54, 2770.
[6] Liu, B.; Tian, H. Chem. Lett. 2005, 34, 686.
[7] Gunnlaugsson, T.; Kruger, P. E.; Jensen, P.; Tierney, J.; Ali, H. D. P.; Hussey, G. M. J. Org. Chem. 2005, 70, 10875.
[8] Zhang, Y.; Xu, W.; Yao, H.; Wei, T. Chin. J. Chem. 2006, 24, 1406.
[9] Wei, W.; Zhang, Y.; Wei, T. Chin. J. Chem. 2008, 26, 1935.
[10] Cao, C.; Wei, T.; Wang, A.; Lin, Q.; Yao, H.; Zhang, Y. Prog. Chem. 2011, 23, 1069 (in Chinese). (曹成, 魏太保, 王爱霞, 林奇, 姚虹, 张有明, 化学进展, 2011, 23, 1069.)
[11] Liu, Y.; Zhang, F.; Zou, L.; Jian, J.; Bao, X. Chin. J. Org. Chem. 2013, 33, 2485 (in Chinese). (刘勇, 张峰, 邹林波, 蹇军友, 鲍小平, 有机化学, 2013, 33, 2485.)
[12] Zhang, F.; Tan, Z.; Yan, B.; Pan, D.; Bao, X. Chin. J. Org. Chem. 2014, 34, 2499 (in Chinese). (张峰, 谭赞, 闫柏任, 潘顶伍, 鲍小平, 有机化学, 2014, 34, 2499.)
[13] Chen, J.; Liu, C.; Zhang, J.; Ding, W.; Zhou, M.; Wu, F. Chem. Commun. 2013, 49, 10814.
[14] De Silva, A. P.; Gunaratne, H. Q. N.; Gunnlaugsson, T.; Huxley, A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515.
[15] Valeur, B.; Pouget, J.; Bourson, J.; Kaschke, M.; Ernsting, N. P. J. Phys. Chem. 1992, 96, 6545.
[16] Bourson, J.; Pouget, J.; Valeur, B. J. Phys. Chem. 1993, 97, 4552.
[17] Schneider, H. J.; Kramer, R.; Simova, S.; Schneider, U. J. Am. Chem. Soc. 1988, 110, 6442.
[18] Wu, F.-Y.; Li, Z.; Wen, Z.-C.; Zhou, N.; Zhao, Y.-F.; Jiang, Y.-B. Org. Lett. 2002, 4, 3203.
[19] Liu, S.-Y.; Fang, L.; He, Y.-B.; Chan, W.-H.; Yung, K.-T.; Cheng, Y.-K.; Yang, R.-H. Org. Lett. 2005, 7, 5825.
[20] Bao, X.; Yu, J.; Zhou, Y. Sens. Actuators B 2009, 140, 467.
[21] Bao, X.; Zhou, Y. Sens. Actuators B 2010, 147, 434.
[22] Zhou, Y.-H.; Zheng, P.-C.; Bao, X.-P. Supramol. Chem. 2014, 26, 761.
[23] Chmielewski, M. J.; Charon, M.; Jurczak, J. Org. Lett. 2004, 6, 3501.
/
| 〈 |
|
〉 |
