Hg2+-Selective Fluorescent Chemosensor Based on Cation-π Interaction

doi:10.1007/s40242-014-4094-y

Chemical Research in Chinese Universities ›› 2014, Vol. 30 ›› Issue (6): 910-914.doi: 10.1007/s40242-014-4094-y

• Articles • Previous Articles Next Articles

Hg²⁺-Selective Fluorescent Chemosensor Based on Cation-π Interaction

YANG Huixiao^1,2, HU Qinzhi^1,2, MA Guochun^1,2, CHEN Guofeng^1,2, TAO Minli^1,2, ZHANG Wenqin^1,2

1. Department of Chemistry, School of Science, Tianjin 300072, P. R. China;
2. Collaborative Innovation Center of Chemical Science and Engineering(Tianjin), Tianjin University, Tianjin 300072, P. R. China

Received:2014-03-19 Revised:2014-05-13 Online:2014-12-01 Published:2014-05-26
Contact: TAO Minli E-mail:mltao@tju.edu.cn
Supported by:
Supported by the National Natural Science Foundation of China(No.21306133) and the Tianjin Research Program of Application Foundation and Advanced Technology, China(No.14JCYBJC22600).

Abstract

Abstract:

Two sulphur-containing 4-aminonaphthalimide derivatives were investigated as Hg²⁺ fluorescent chemosensors. In CH₃CN, both sensors present a remarkable fluorescence enhancement to Cu²⁺ and Fe³⁺, but a selective fluorescence quenching to Hg²⁺ among the other metal ions. A cation-π interaction between Hg²⁺ and the naphthalimide moiety was proposed and confirmed by the density functional theory(DFT).

Key words: 4-Aminonaphthalimide, Fluorescent chemosensor, Cation-π interaction, Hg²⁺, Density functional theory (DFT)

YANG Huixiao, HU Qinzhi, MA Guochun, CHEN Guofeng, TAO Minli, ZHANG Wenqin. Hg²⁺-Selective Fluorescent Chemosensor Based on Cation-π Interaction[J]. Chemical Research in Chinese Universities, 2014, 30(6): 910-914.

References

[1] De Silva A. P., Gunaratne. H. N., Gunnlaugsson T., Huxley A. J., McCoy C. P., Rademacher J. T., Rice T. E., Chem. Rev., 1997, 97(5), 1515
[2] Boening D. W., Chemosphere, 2000, 40(12), 1335
[3] Benoit J. M., Fitzgerald W. F., Damman A. W. H., Environ. Res., 1998,78(2), 118
[4] He S., Liu Q., Li Y., Wei F., Cai S., Lu Y., Zeng X., Chem. Res. Chinese Universities, 2014, 30(1), 32
[5] Su W. Q., Yang B. Q., Chem. Res. Chinese Universities, 2013,29(4)，657
[6] Caballero A., Martínez R., Lloveras V., Ratera I., Vidal-Gancedo J., Wurst K., Tárraga A., Molina P., Veciana J., J. Am. Chem. Soc., 2005, 127(45), 15666
[7] Coskun A., Akkaya E. U., J. Am. Chem. Soc., 2006, 128(45), 14474
[8] Avirah R. R., Jyothish K., Ramaiah D., Org. Lett., 2007, 9(1), 121
[9] Kim S. H., Kim J. S., Park S. M., Chang S. K., Org. Lett., 2006, 8(3), 371
[10] Choi M. J., Kim M. Y., Chang S. K., Chem. Commun., 2001, 17, 1664
[11] Youn N. J., Chang S. K., Tetrahedron Lett., 2005, 46(1), 125
[12] Moon S. Y., Youn N. J., Park S. M., Chang S. K., J. Org. Chem., 2005, 70(6), 2394
[13] Cheng Y. F., Zhao D. T., Zhang M., Liu Z. Q., Zhou Y. F., Shu T. M., Li F. Y., Yi T., Huang C. H., Tetrahedron Lett., 2006, 47(36), 6413
[14] Park S. M., Kim M. H., Choe J. I., No K. T., Chang S. K., J. Org. Chem., 2007, 72(9), 3550
[15] Lee M. H., Wu J. S., Lee J. W., Jung J. H., Kim J. S., Org. Lett., 2007, 9(13), 2501
[16] Wu J. S., Hwang I. C., Kim K. S., Kim J. S., Org. Lett., 2007, 9(5), 907
[17] Suelter C., Science, 1970, 168(3933), 789
[18] McRee D. E., Nat. Struct. Biol., 1998, 5, 8
[19] Agranoff D. D., Krishna S., Mol. Microbiol., 1998, 28(3), 403
[20] Pyle A., J. Biol. Inorg. Chem., 2002, 7(7/8), 679
[21] Masson E., Schlosser M., Org. Lett., 2005, 7(10), 1923
[22] Murayama K., Aoki K., Inorg. Chim. Acta, 1998, 281(1), 36
[23] De Wall S. L., Meadows E. S., Barbour L. J., Gokel G. W., J. Am. Chem. Soc., 1999, 121(23), 5613
[24] Reddy A. S., Zipse H., Sastry G. N., J. Phys. Chem. B, 2007, 111(39), 11546
[25] Zari? S. D., Chem. Phys. Lett., 1999, 311(1), 77
[26] Lau W., Huffman J. C., Kochi J. K., J. Am. Chem. Soc., 1982, 104(20), 5515
[27] Lau W., Kochi J., J. Org. Chem., 1986, 51(10), 1801
[28] Fages F., Desvergne J. P., Bouas-Laurent H., Marsau P., Lehn J. M., Kotzyba-Hibert F., Albrecht-Gary A. M., Al-Joubbeh M., J. Am. Chem. Soc., 1989, 111(23), 8672
[29] Ishikawa J., Sakamoto H., Nakao S., Wada H., J. Org. Chem., 1999, 64(6), 1913
[30] Yi H. B., Lee H. M., Kim K. S., J. Chem. Theory Comput., 2009, 5(6), 1709
[31] Lee S., Lee J. H., Pradhan T., Lim C. S., Cho B. R., Bhuniya S., Kim S., Kim J. S., Sens. Actuator B, 2011, 160(1), 1489
[32] Xu S., Li W., Chen K. C., Chin. J. Chem., 2007, 25(6), 778
[33] Guo X. F., Zhu B. C., Liu Y. Y., Zhang Y., Jia L. H., Qian X. H., Chin. J. Org. Chem., 2006, 26(4), 504
[34] Springer C. J., Dowell R., Burke P. J., Hadley E., Davies D. H., Blakey D. C., Melton R. G., Niculescu-Duvaz I., J. Med. Chem., 1995, 38(26), 5051
[35] Tanaka M., Nakamura M., Ikeda T., Ikeda K., Ando H., Shibutani Y., Yajima S., Kimura K., J. Org. Chem., 2001, 66(21), 7008
[36] Zhang Z. Y., Chen Y. H., Xu D. M., Yang L., Liu A. F., Spectroc. Acta Pt. A, Molec. Biomolec. Spectr., 2013, 105, 8
[37] Miehlich B., Savin A., Stoll H., Preuss H., Chem. Phys. Lett., 1989, 157(3), 200
[38] Lee C., Yang W., Parr R. G., Phys. Rev. B, 1988, 37(2), 785
[39] Hay P. J., Wadt W. R., J. Chem. Phys., 1985, 82(1), 270
[40] Hay P. J., Wadt W. R., J. Chem. Phys., 1985, 82(1), 299
[41] Hay P. J., Wadt W. R., J. Chem. Phys., 1985, 82(1), 284
[42] Frisch M. J., Trucks G. W., Schlegel H. B., et al, Gaussian 03, Walligford, CT, 2004
[43] Kuzmi? P., Anal. Biochem., 1996, 237(2), 260

Hg²⁺-Selective Fluorescent Chemosensor Based on Cation-π Interaction

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 6

Recommended Articles

Metrics

Comments

[1]	WANG Shuxin, CAO Jian, CHENG Yuxiao, LU Chenhong. A Sensitive Fluorescent Turn-on Probe NapP-deap Based on Naphthalimide Derivative to Detect Hg(II) Ions in HEPES Buffer Solution and Living Cells [J]. Chemical Research in Chinese Universities, 2019, 35(6): 967-971.
[2]	WU Shuo, YANG Xinlan, ZHAO Yanqiu. Ru(II) Bipyridyl Complex and TiO₂ Nanocomposite Based Biomolecule-free Photoelectrochemical Sensor for Highly Selective Determination of Ultra-trace Hg²⁺ in Aqueous Systems [J]. Chemical Research in Chinese Universities, 2019, 35(3): 370-376.
[3]	FENG Jia, SHAO Xiuqing, SHANG Zhuobin, CHAO Jianbin, WANG Yu, JIN Weijun. A New Biphenylcarbonitrile Based Fluorescent Sensor for Zn²⁺ Ions and Application in Living Cells [J]. Chemical Research in Chinese Universities, 2017, 33(5): 695-701.
[4]	FENG Huiyun, GAO Lei, YE Xinhui, WANG Lei, XUE Zechun, KONG Jinming, LI Lianzhi. Synthesis of a Heptapeptide and Its Application in the Detection of Mercury(II) Ion [J]. Chemical Research in Chinese Universities, 2017, 33(2): 155-159.
[5]	HE Song, LIU Qiuchen, LI Yuanyuan, WEI Fangfang, CAI Songtao, LU Yan, ZENG Xianshun. Rhodamine 6G-based Chemosensor for the Visual Detection of Cu²⁺ and Fluorescent Detection of Hg²⁺ in Water [J]. Chemical Research in Chinese Universities, 2014, 30(1): 32-36.
[6]	SU Wen-qi, YANG Bing-qin. Novel Highly Selective Fluorescent Chemosensors for Hg(II) [J]. Chemical Research in Chinese Universities, 2013, 29(4): 657-662.