A selective and sensitive “naked-eye” rhodamine-based “turn-on” sensor for recognition of Hg2+ ion in aqueous solution

Yuanyuan Yan; Guodong Ding; Hui Xu

Journal of Industrial and Engineering Chemistry, Vol.25, 73-77, May, 2015

DOI10.1016/j.jiec.2014.10.015 Export Citation

A selective and sensitive “naked-eye” rhodamine-based “turn-on” sensor for recognition of Hg2+ ion in aqueous solution

Yuanyuan Yan¹, Guodong Ding¹, and Hui Xu^{1, 2, †}

¹Research Institute of Pesticidal Design & Synthesis, College of Sciences/Plant Protection, Northwest A&F University, Yangling 712100, Shaanxi Province, People’s Republic of China
²State Key Laboratory of Crop Stress Biology for Arid Areas, Northwest A&F University, Yangling 712100, Shaanxi Province, People’s Republic of China

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A selective and sensitive “naked-eye” rhodamine-based “turn-on” chemosensor for detection of Hg2+ ion over other metal ions such as Ni2+, Ca2+, Ba2+, Cs+, Fe3+, Mn2+, Cd2+, Zn2+, Mg2+, K+, Ag+, Hg2+, Co2+, and Pb2+ in aqueous solution was prepared. Meanwhile, a new method for the synthesis of rhodamine amide directly from rhodamine hydrazide in the presence of NaH was reported for the first time. It was observed that once Hg2+ ion was added to the sensor 4, a 91.4-fold enhancement of the absorption at 570 nm was observed. Its selectivity toward Hg2+ ion was very high, and little interference was detected for other commonly coexistent metal ions. The fluorescent intensity was almost a constant minimal value when pH = 5?8 in aqueous solution. It demonstrated that Hg2+ could be detected at least down to 3 × 10?8 M. Moreover, the Hg2+-promoted selective desulfurization reaction was further confirmed by MS spectra. The present probe could be used to determine Hg2+ ion concentrations in aqueous environments.

Keywords:Fluorescence;Probe;Naked-eye;Mercury ion;Turn-on;Desulfurization

[References]

Kim HN, Ren WX, Kim JS, Yoon J, Chem. Soc. Rev., 41, 3210 (2012)
Descalzo AB, Martinez-Manez R, Radeglia R, Rurack K, Soto J, J. Am. Chem. Soc., 125(12), 3418 (2003)
Li D, Campbell LD, Austin BA, Koide K, ChemPlusChem, 77, 281 (2012)
Souto RM, Gonzalez-Garcia Y, Battistel D, Daniele S, Chem. Eur. J., 18, 230 (2012)
Won JH, Lee JY, Chung D, Shin SK, Lee TG, J. Ind. Eng. Chem., 19(5), 1560 (2013)
Sangsefidi FS, Salavati-Niasari M, Esmaeili-Zare M, J. Ind. Eng. Chem., 20(5), 3415 (2014)
Cho JH, Eom Y, Jeon SH, Lee TG, J. Ind. Eng. Chem., 19(1), 144 (2013)
Lee MH, Lee SW, Kim SH, Kang C, Kim JS, Org. Lett., 11, 2101 (2009)
Lee MH, Cho BK, Yoon J, Kim JS, Org. Lett., 9, 4515 (2007)
Wu JS, Hwang IC, Kim KS, Kim JS, Org. Lett., 9, 907 (2007)
Choi MG, Kim YH, Namgoong JE, Chang SK, Chem. Commun., 24, 3560 (2009)
Jiang W, Wang W, Chem. Commun., 26, 3913 (2009)
Dujols V, Ford F, Czarnik AW, J. Am. Chem. Soc., 119(31), 7386 (1997)
Yang YK, Yook KJ, Tae J, J. Am. Chem. Soc., 127(48), 16760 (2005)
Kwon JY, Jang YJ, Lee YJ, Kim KM, Seo MS, Nam W, Yoon J, J. Am. Chem. Soc., 127(28), 10107 (2005)
Weerasinghe AJ, Schmiesing C, Sinn E, Tetrahedron Lett., 50, 6407 (2009)
Hu Z, Huang W, Li M, Xu MZH, Zhang LK, Guo R, Xiang TC, Wu CZ, Zheng Z, Yang FL, Sens. Actuators B-Chem., 156, 546 (2011)
Dong M, Ma TH, Zhang AJ, Dong YM, Wang YW, Peng Y, Dyes Pigment., 87, 164 (2010)
Yan Y, Che Z, Yu X, Zhi X, Wang J, Xu H, Bioorg. Med. Chem., 21, 508 (2013)
Guo Y, Yan Y, Zhi X, Yang C, Xu H, Bioorg. Med. Chem. Lett., 23, 3382 (2013)
Yan Y, Zhang Y, Xu H, ChemPlusChem, 78, 628 (2013)
Dai HL, Yan YY, Guo Y, Fan LL, Che ZP, Xu H, Chem. Eur. J., 18, 11188 (2012)
Huang W, Song CX, He C, Lv GJ, Hu XY, Zhu X, Duan CY, Inorg. Chem., 48(12), 5061 (2009)

[Referenced By]

[1] Kim HN, Ren WX, Kim JS, Yoon J, Chem. Soc. Rev., 41, 3210 (2012)

[2] Descalzo AB, Martinez-Manez R, Radeglia R, Rurack K, Soto J, J. Am. Chem. Soc., 125(12), 3418 (2003)

[3] Li D, Campbell LD, Austin BA, Koide K, ChemPlusChem, 77, 281 (2012)

[4] Souto RM, Gonzalez-Garcia Y, Battistel D, Daniele S, Chem. Eur. J., 18, 230 (2012)

[5] Won JH, Lee JY, Chung D, Shin SK, Lee TG, J. Ind. Eng. Chem., 19(5), 1560 (2013)

[6] Sangsefidi FS, Salavati-Niasari M, Esmaeili-Zare M, J. Ind. Eng. Chem., 20(5), 3415 (2014)

[7] Cho JH, Eom Y, Jeon SH, Lee TG, J. Ind. Eng. Chem., 19(1), 144 (2013)

[8] Lee MH, Lee SW, Kim SH, Kang C, Kim JS, Org. Lett., 11, 2101 (2009)

[9] Lee MH, Cho BK, Yoon J, Kim JS, Org. Lett., 9, 4515 (2007)

[10] Wu JS, Hwang IC, Kim KS, Kim JS, Org. Lett., 9, 907 (2007)

[11] Choi MG, Kim YH, Namgoong JE, Chang SK, Chem. Commun., 24, 3560 (2009)

[12] Jiang W, Wang W, Chem. Commun., 26, 3913 (2009)

[13] Dujols V, Ford F, Czarnik AW, J. Am. Chem. Soc., 119(31), 7386 (1997)

[14] Yang YK, Yook KJ, Tae J, J. Am. Chem. Soc., 127(48), 16760 (2005)

[15] Kwon JY, Jang YJ, Lee YJ, Kim KM, Seo MS, Nam W, Yoon J, J. Am. Chem. Soc., 127(28), 10107 (2005)

[16] Weerasinghe AJ, Schmiesing C, Sinn E, Tetrahedron Lett., 50, 6407 (2009)

[17] Hu Z, Huang W, Li M, Xu MZH, Zhang LK, Guo R, Xiang TC, Wu CZ, Zheng Z, Yang FL, Sens. Actuators B-Chem., 156, 546 (2011)

[18] Dong M, Ma TH, Zhang AJ, Dong YM, Wang YW, Peng Y, Dyes Pigment., 87, 164 (2010)

[19] Yan Y, Che Z, Yu X, Zhi X, Wang J, Xu H, Bioorg. Med. Chem., 21, 508 (2013)

[20] Guo Y, Yan Y, Zhi X, Yang C, Xu H, Bioorg. Med. Chem. Lett., 23, 3382 (2013)

[21] Yan Y, Zhang Y, Xu H, ChemPlusChem, 78, 628 (2013)

[22] Dai HL, Yan YY, Guo Y, Fan LL, Che ZP, Xu H, Chem. Eur. J., 18, 11188 (2012)

[23] Huang W, Song CX, He C, Lv GJ, Hu XY, Zhu X, Duan CY, Inorg. Chem., 48(12), 5061 (2009)