Coumarin modified rhodamine derivative: Fluorescent chemosensor selectively recognizing Al³⁺ and Ca²⁺

Abstract

A fluorescent probe with a coumarin moiety bound to rhodamine 6G hydrazide(1) was synthesized. Its sensing behavior toward various metal ions was investigated with fluorescence methods. Compound 1 displays different fluorescence emission responses to Al³⁺ and Ca²⁺ at the same excitation wavelength in the visible light region, while no changes occur after the addition of other metal ions. The binding ratios of the complexs of 1-Al³⁺ and 1-Ca²⁺ are both 2:1 according to the Job plot and high resolution mass spectrometer(HRMS) experiments. Moreover, emission spectrum of 1-Ca²⁺ complex and absorption spectrum of the rhodamine dyes overlap largely. When Al³⁺ was added to the 1-Ca²⁺ system, calcium in complex 1-Ca²⁺ can be displaced by Al³⁺, resulting in the output of another ratiometric sensing signal, which demonstrates that the 1-Ca²⁺ complex can be served as a new and effective fluorescence resonance energy transfer(FRET) donor for rhodamine derivatives.

Keywords

Chemosensor / Aluminium ion / Calcium ion / Fluorescence resonance energy transfer(FRET)

References

[1] Zhang J F, Zhou Y, Yoon J Y, Kim S J, Kim J S. Org. Lett., 2010, 12: 3852.

[2] Lei Z J, Zhang C Z, Hu Q H, Liu Y, Zhang Q, Liu X J. Chin. J. Anal. Chem., 2012, 40: 1827.

[3] Robinson G H. Chem. Eng. News, 2003, 81: 54.

[4] Altschuler E. Med. Hypotheses, 1999, 53: 22.

[5] Wang B, Xing W, Zhao Y, Deng X. Environ. Toxicol. Phar., 2010, 29: 308.

[6] Walton J R. Neurotoxicology, 2006, 27: 385.

[7] Polizzi S. Neurotoxicology, 2002, 23: 761.

[8] Hahn S H, Tanner M S, Danke D M, Gahl W A. Biochem. Mol. Med., 1995, 54: 142.

[9] Berridge M J. Nature, 1993, 361: 315.

[10] Strieker S A, Centonze V E, Paddock S W, Schattenet G. Dev. Biol., 1992, 149: 370.

[11] Whitaker M, Patel R. Development, 1990, 108: 525.

[12] Clapham D E. Cell, 1995, 80: 259.

[13] Carafoli E. Proc. Natl. Acad. Sci., 2002, 99: 1115.

[14] Kim S H, Choi H S, Kim J, Lee S J, Quang D T, Kim J S. Org. Lett., 2010, 12: 560.

[15] DeSilva 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] Wang L N, Qin W W, Tang X L, Dou W, Liu W S, Teng Q F, Yao X J. Org. Biomol. Chem., 2010, 8: 3751.

[17] Gou C, Qin S H, Wu H Q, Wang Y, Luo J, Liu X Y. Inorg. Chem. Commun., 2011, 14: 1622.

[18] Kim J, Morozumi T, Nakamura H. Org. Lett., 2007, 9: 4419.

[19] Emrullahoglu M, Karakus E, Ucuncu M. Chem. Commun., 2013, 49: 7836.

[20] Zhou X, Yan W, Zhao T, Tian Z X, Wu X. Tetrahedron, 2013, 69: 9535.

[21] Neupane L N, Park J Y, Park J H, Lee K H. Org. Lett., 2013, 15: 254.

[22] Liu S K, Zhou C Y, Du J H, Gao J G, Zhou J. Chin. J. Anal. Chem., 2013, 41: 732.

[23] Kim H N, Lee M H, Kim H J, Kim J S, Yoon J. Chem. Soc. Rev., 2008, 37: 1465.

[24] Mao J, Wang L N, Dou W, Tang X L, Yan Y, Liu W S. Org. Lett., 2007, 9: 4567.

[25] Suzuki Y, Komatsu H, Iked T, Saito N, Araki S, Citterio D, Hisamoto H, Kitamura Y, Kubota T, Nakagawa J, Oka K, Suzuki K. Anal. Chem., 2002, 74: 1423.

[26] Lin W Y, Yuan L, Feng J B. Eur. J. Org. Chem., 2008, 16: 3821.

[27] Yuan L, Lin W Y, Chen B, Xie Y N. Org. Lett., 2012, 14: 432.

[28] An J M, Yang Z J, Yan M H, Li T R. J. Lumin., 2013, 139: 79.

[29] Ma Q J, Zhang X B, Zhao X H, Jin Z, Mao G J, Shen G L, Yu R Q. Anal. Chim. Acta, 2010, 663: 85.

[30] Liu W Y, Li H Y, Lü H S, Zhao B X, Miao J Y. Spectrochim. Acta Part A, 2012, 95: 658.

[31] Goswamia S, Sena D, Dasa A K, Dasa N K. Sens. Actuators B, 2013, 183: 518.

[32] Lee K S, Kim H J, Kim G H, Shin I, Hong J I. Org. Lett., 2008, 10: 49.

[33] Cao B N, Hu Q, Huang Y, Jia C M, Zhang Q. Chem. Res. Chinese Universities, 2013, 29(3): 419.

[34] Yuan L, Lin W Y, Yang Y T, Song J Z. Chem. Commun., 2011, 47: 4703.

[35] Martin R B. Acc. Chem. Res., 1994, 27: 204.

[36] Yang X F, Zhao M L, Wang G. Sens. Actuators B, 2011, 152: 8.