A Novel 2-Phenyl-1,2,3-Triazole Derived Fluorescent Probe for Recyclable Detection of Al 3+ in Aqueous Medium and Its Ap
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Novel 2-Phenyl-1,2,3-Triazole Derived Fluorescent Probe for Recyclable Detection of Al3+ in Aqueous Medium and Its Application Zhengfeng Xiea, 1, Yunpeng Haoa, Zhen Lib, Fanghua Suna, Junchi Maa, Xin Chena, Wei Shia, and Shun Fengb, 2 aOil
and Gas Field Applied Chemistry Key Laboratory of Sichuan Province, College of Chemistry and Chemical Engineering, Southwest Petroleum University, Chengdu, 610500 China b School of Life Science and Engineering, Southwest Jiaotong University, Chengdu, 610031 China Received July 25, 2019; revised August 9, 2019; accepted September 16, 2019
Abstrast—A novel 2-phenyl-1,2,3-triazole derived fluorescent probe HPTC ((2-hydroxybenzylidene)-2phenyl-2H-1,2,3-triazole-4-carbohydrazide) has been designed and synthesized for recyclable detection of Al3+ in DMSO/Tris-HCl (pH 7.4) 1 : 100 v/v with high sensitivity and selectivity. A fluorescence enhancement of 97 folds at 457 nm can be realized upon addition of 10.0 equiv. Al3+ with excitation at 375 nm. The binding constant of HPTC with Al3+ and the detection limit of HPTC toward Al3+ were 1.67 × 105 M–1 and 8.875 × 10–8 M, respectively. In addition, the probe HPTC can detect Al3+ repeatedly in DMSO/Tris-HCl (pH 7.4) 1 : 100 v/v and the detection effect is not changed. The probe HPTC showed an excellent detection ability in a wide pH range from 3 to 10 and also in living cells. Furthermore, the Al3+ sensing mechanism was confirmed based on Job’s plot, 1H NMR titration, HR-MS, and DFT studies. Finally, HPTC-doped agarose hydrogel experiment suggests that the HPTC can recognize the Al3+ in solid state. Keywords: fluorescent probe, 2-phenyl-1,2,3-triazole, aluminum ion, bioimaging DOI: 10.1134/S1068162020040214
INTRODUCTION As the third most abundant metal in the crust, aluminum is extensively used in industries and modern daily life, such as alloy materials, conductive materials, packaging materials, pharmaceuticals, food additives, water purifying agent, etc. [1–8]. Because of the wide application of aluminum, the research has found that when the concentration of Al3+ is present in overload quantities, it can cause serious risks to the health of animals and plants and even put away with many species in the ecosystem [9–11]. The excessive Al3+ in the human body may also lead to the emergence of diseases, such as Alzheimer’s disease, neurasthenia, breast cancer, osteomalacia, and Parkinson’s disease. Hence, it is urgently desirable to synthesize a high sensitivity, good selectivity, simplicity, wide range of pH, and short-time Al3+ fluorescent probe in environmental and biological systems [12, 13]. In recent years, a series of probes for Al3+ have been reported, including imine [14–19], acylhydrazone 1 Corresponding
author: phone: +86 28 83037306; fax: +86 28 83037305; e-mail: [email protected]. 2 Corresponding author: e-mail: [email protected].
[20], carbon dots [21], metal-organic framework [22], and photochromic diarylethene [23] probes. Among them, acylhydrazone compounds have gained interest due to the CONHN=CH moiety with strong c
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