Derivatives of Aminobenzoic Acid Hydrazide-Based Fluorescence Probe for Selective Recognition of Cr3+
WU Hong-mei1, GUO Yu1*, CAO Jian-fang1, WU Zhong-li2
1. School of Chemical and Environmental Engineering, Liaoning University of Technology, Jinzhou 121001, China
2. College of Mechanical Engineering and Automation, Liaoning University of Technology, Jinzhou 121001, China
Abstract：A novel and simple fluorescence probe L ((E)-4-(1-(dimethylamino)naphthalene-5-sulfonamido)-N′-((2-hydroxynaphthalen-1-yl)methylene)benzohydrazide) for detection of Cr3+ was prepared by the Introduction of dansyl sulfonamide fluorescent group and 2-hydroxy-1-naphthalaldehyde coordination group to p-aminobenzoic acid with chemical derivatization method. The structure of the probe L was investigated by 1H NMR, ESI-MS and FT-IR. The effect of probe L for recognition of Cr3+ was studied by fluorescence spectroscopy. The results show that the probe L shows a double peak at 473 nm (2-hydroxy-1-naphthaldehyde) and 514 nm (dansyl sulfonamide) when the excitation wavelength is 350 nm. After the addition of Cr3+ to the probe L, 2-hydroxy-1-naphthaldehyde was bonded to Cr3+, and the emission peak of dansylamine was red shifted to 540 nm (dansylamine characteristic peak). The intensity of fluorescence was increased by five times and the fluorescence quantum yield Φ was up to 0.28. The background fluorescence of the probe L has no effect on the recognition of Cr3+. The recognition process is presumed to be caused by the CHEF effect combined with PET (photoinduced electron transfer) mechanism. When the other metal ions were added, such as Na+, K+, Li+, Ca2+, Zn2+, Mn2+, Co2+, Cu2+, Cd2+, Hg2+, Pb2+, Ag+, the fluorescence intensity was not enhanced at 540 nm, indicating that the probe L had a high specific selectivity for Cr3+. A 1∶1 complexation stoichiometry for the binding mode of Cr3+ with L was confirmed by the model of the Job’s plot and ESI-MS result. The detection limit of L for Cr3+ was up to 4.0×10-6 mol·L-1.
Key words：Chromium ion; Fluorescence; Derivatives of aminobenzoic acid hydrazide; Probe
[1] Lohar S, Banerjee A, Sahana A, et al. Anal. Methods, 2013, 5： 442.
[2] Saeed A A, Sandhu M A, Khilji M S, et al. J. Trace Elem. Med. Bio., 2017, 42： 25.
[3] Huang S, Xia W, Li Y Y, et al. Environ. Pollut., 2017, 230： 53.
[4] Beyki M H, Alijani H, Fazli Y. Process Saf. Environ., 2016, 102： 687.
[5] Martino A D, Iorio M, Capasso R. Chemosphere, 2013, 92： 1436.
[6] Mao Y, Hong M M, Liu A F, et al. J. Fluoresc., 2015, 25： 755.
[7] Chen X Q, Pradhan T, Wang F, et al. Chem. Rev., 2012, 112： 1910.
[8] Du J, Hu M, Fan J, et al. Chem. Soc. Rev., 2012, 41： 4511.
[9] Geng T M, Wu D Y, Huang W, et al. J. Polym. Res., 2014, 21： 354.
[10] Su J, Huang S S, He S, et al. Chem. Res. Chin. Univ., 2016, 32： 20.
[11] CHEN Jia-yi, SU Wei, WANG En-jun(陈家逸, 苏 伟, 王恩举). Chem. J. Chin. Univ.(高等学校化学学报), 2016, 37： 232.
[12] Zhou Y, Zhang J, Zhang L, et al. Dyes Pigm., 2013, 97： 148.
[13] Dhara A, Guchhait N, Kar S K. J. Fluoresc., 2015, 25： 1921.
[14] Wu S, Zhang K, Wang Y, et al. Tetrahedron Lett., 2014, 55： 351.
[15] Renaud R, Alexandre N, Abdelkarim A. Anal. Chem., 2016, 88： 666.
[16] Mahajan P G, Bhopate D P, Kolekar G B, et al. Sensor Actuators B. Chem., 2015, 220： 864.
[17] Arturo J S, Norberto F, Rosa S. Tetrahedron Lett., 2013, 54： 5279.
[18] ZHANG Peng, ZHANG You-ming, LI Qi, et al(张 鹏, 张有明, 林 奇, 等). Chin. J. Org. Chem.(有机化学), 2014, 34： 1300.
