Chinese Journal of Organic Chemistry >
Synthesis and Recognition Properties of Carbazole Sulfonamide-Based Anion Receptor Containing the Aminoanthraquinone Signalling Units
Received date: 2015-12-11
Revised date: 2016-01-21
Online published: 2016-02-02
Supported by
Project supported by the National Natural Science Foundation of China (No. 21161005).
A novel carbazole sulfonamide-based anion receptor (L) containing the aminoanthraquinone signalling units was designed and synthesized, which was characterized by 1H NMR, 13C NMR, MS, IR and elemental analysis. The obtained results from UV-Vis and fluorescence titrations indicated that receptor L realized a highly selective recognition of F- via the formation of a 1:1 H-bonding complex. Moreover, the presence of F- induced a significant fluorescent quenching and a color change (from red to purple-red) of dimethyl sulfoxide (DMSO) solution of L, suggesting its potential as fluorescent and colorimetric sensors for the detection of F-.
Tan Zan, Du Huan, Lü Xinyang, Bao Xiaoping . Synthesis and Recognition Properties of Carbazole Sulfonamide-Based Anion Receptor Containing the Aminoanthraquinone Signalling Units[J]. Chinese Journal of Organic Chemistry, 2016 , 36(6) : 1389 -1394 . DOI: 10.6023/cjoc201512016
[1] Schmidtchen, F. P.; Berger, M. Chem. Rev. 1997, 97, 1609.
[2] Wenzel, M.; Hiscock, J. R.; Gale, P. A. Chem. Soc. Rev. 2012, 41, 480.
[3] Miao, R.; Zheng, Q.-Y.; Chen, C.-F.; Huang, Z.-T. Tetrahedron Lett. 2005, 46, 2155.
[4] Chen, Q.-Y.; Chen, C.-F. Tetrahedron Lett. 2004, 45, 6493.
[5] Ayoob, S.; Gupta, A. K. Crit. Rev. Environ. Sci. Technol. 2006, 36, 433.
[6] Zhou, Y.; Zhang, J. F.; Yoon, J. Chem. Rev. 2014, 114, 5511.
[7] Zhang, F.; Tan, Z.; Yan, B.-R.; Pan, D.-W.; Bao, X.-P. 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.)
[8] Sakai, R.; Barasa, E. B.; Sakai, N.; Sato, S.-I.; Satoh, T.; Kakuchi, T. Macromolecules 2012, 45, 8221.
[9] Chen, C.-F.; Chen, Q.-Y. Tetrahedron Lett. 2004, 45, 3957.
[10] Lu, H.; Xu, W.; Zhang, D.; Chen, C.; Zhu, D. Org. Lett. 2005, 7, 4629.
[11] Jung, H. S.; Kim, H. J.; Vicens, J.; Kim, J. S. Tetrahedron Lett. 2009, 50, 983.
[12] 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.)
[13] Jian, J.-Y.; Yan, B.-R.; Pan, D.-W.; Tan, Z.; Lv, X.-Y.; Du, H.; Bao, X.-P. Chin. J. Org. Chem. 2015, 35, 1069 (in Chinese). (蹇军友, 闫柏任, 潘顶伍, 谭赞, 吕新阳, 杜欢, 鲍小平, 有机化学, 2015, 35, 1069.)
[14] Chen, J.-J.; Liu, C.-X.; Zhang, J.-L.; Ding, W.; Zhou, M.; Wu, F.-H. Chem. Commun. 2013, 49, 10814.
[15] 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.
[16] Valeur, B.; Pouget, J.; Bourson, J.; Kaschke, M.; Ernsting, N. P. J. Phys. Chem. 1992, 96, 6545.
[17] Bourson, J.; Pouget, J.; Valeur, B. J. Phys. Chem. 1993, 97, 4552.
[18] Liu, S.-Y.; Fang, L.; He, Y.-B.; Chan, W.-H.; Yeung, K.-T.; Cheng, Y.-K.; Yang, R.-H. Org. Lett. 2005, 7, 5825.
[19] Zhou, Y.-H.; Zheng, P.-C.; Bao, X.-P. Supramol. Chem. 2014, 26, 761. Kowalczyk, A.; Nowicka, A. M.; Jurczakowski, R.; Niedzial- kowski, P.; Ossowski, T.; Stojek, Z. Electroanalysis 2010, 22, 49.
/
〈 |
|
〉 |