Novel fluorescent chemosensors based on tryptophan unit for Cu²⁺ and Fe³⁺ in aqueous solution

Abstract

We reported four fluorescent chemosensors containing tryptophan units. The fluorescence spectrum titration experiments suggest that chemosensors 1, 2, 3 and 4 are highly selective for Cu²⁺ and Fe³⁺ over Li⁺, Na⁺, K⁺, Co²⁺, Zn²⁺, Ni²⁺, Hg²⁺ and Cr³⁺ via forming complexes with Cu²⁺ or Fe³⁺, which is confirmed by dramatical quench of fluoreseence in aqueous solution at pH 7.4, thus making all the chemosensors suitable for Cu²⁺ and Fe³⁺ fluorescent sensors.

Keywords

Fluorescent / Chemosensor / Cu²⁺ / Fe³⁺

References

[1] Zhang L, Wang J, Fan J, Guo K, Peng X. Bioorg. Med. Chem. Lett., 2011, 21: 5413.

[2] Hu G Q, Wang G Q, Duan N N, Wen X Y, Cao T Y, Xie S Q, Huang W L. Chem. Res. Chinese Universities, 2012, 28(6): 980.

[3] Batista R M F, Liveira E, Costa S P G, Lodeiro C, Raposo M M M. Tetrahedron, 2011, 67: 7106.

[4] Praveen L, Reddy M L P, Varma R L. Tetrahedron Lett., 2010, 51: 6626.

[5] Liu X, Yang X, Peng H, Zhu C, Cheng Y. Tetrahedron Lett., 2011, 52: 2295.

[6] Gong Z L, Fei G, Zhao B X. Sens. Actuators B, 2011, 159: 148.

[7] Tang L, Li F, Liu M, Nandhakumar R. Spectrochim. Acta, Part A, 2011, 78: 1168.

[8] Li G K, Xu Z X, Chen C F, Huang Z T. Chem. Commun., 2008, 1774.

[9] Xiao X Z, Chen P, Chen H R. Chem. Res. Chinese Universities, 2012, 28(4): 609.

[10] Gaggelli E, Kozlowski H, Valensin D, Valensin G. Chem. Rev., 2006, 106: 1995.

[11] Chen X, Jou M J, Lee H, Kou S, Lim J, Nam S W, Park S, Kim K M, Yoon J. Sens. Actuator B, 2009, 137: 597.

[12] Lohani C R, Lee K H. Sens. Actuator B, 2010, 143: 649.

[13] Queirós C, Silva A M G, Lopes S C, Ivanova G, Gameiro P, Rangel M. Dyes Pigm., 2012, 93: 1447.

[14] Peng R, Wang F, Sha Y. Molecules, 2007, 12: 1191.

[15] Singh N, Kaur N, Dunn J, MacKay M, Callan J F. Tetrahedron Lett., 2009, 50: 953.

[16] Yao W Y, Xu K X, Kong H J, Kou L, Zhang Q H, Wang C J. Supramol. Chem., 2013, 25: 146.

[17] Li Z, Zhang L, Wang L, Guo Y, Cai L, Yu M, Wei L. Chem. Commun., 2011, 47: 5798.

[18] Wu J S, Wang P F, Zhang X H, Wu S K. Spectrochim. Acta, Part A, 2006, 65: 749.

[19] Wang M X, Yang H B. J. Am. Chem. Soc., 2004, 126: 15412.

[20] Du C P, You J S, Yu X Q, Liu C L, Lan J B, Xie R G. Tetrahedron: Asymmetry, 2003, 14: 3651.

[21] Xu K X, Cheng P F, Zhao J, Wang C J. J. Fluoresc., 2011, 21: 991.

[22] Kragh-Hansen U. Pharmacol. Rev., 1981, 33: 17.

[23] Li W, Liu T, Li Z, Wang Y. J. Solution Chem., 2012, 41: 2009.

[24] Sun Y, Wei S, Yin C, Liu L, Hu C, Zhao Y, Ye Y, Hu X, Fan J. Bioorg. Med. Chem. Lett., 2011, 21: 3798.

[25] Gelamo E L, Silva C H T P, Imasato H, Tabak M. Biochim. Biophys. Acta, 2002, 1594: 84.

[26] Sharma S N, Sharma H, Singh G, Shivaprasad S M. Mater. Chem. Phys., 2008, 110: 471.

[27] Valeur B, Pouget J, Bourson J. J. Phys. Chem., 1992, 96: 6545.