Chinese Journal of Organic Chemistry >
Structural Properties of Ethyl 5-Phenyl-2-(3-(trifluoromethyl)phenyl)-2H-1,2,3-triazole-4-carboxylate and Chromo Genic Responses of Its Rhodamine B Derivatives to Hg2+ Ions
Received date: 2017-09-01
Revised date: 2017-11-11
Online published: 2017-12-08
Supported by
Project supported by the National Natural Science Foundation of China (No. 21562019), the Natural Science Foundation of Hainan Province (No. 20162027), the Hainan Province Natural Science Foundation of Innovative Research Team Project (No. 2016CXTD007) and the Program of Hainan Association for Science and Technology Plans to Youth R & D Innovation (No. HAST201621).
Ethyl 5-phenyl-2-(3-(trifluoromethyl)phenyl)-2H-1,2,3-triazole-4-carboxylate (EPFC), a newly synthesized compound, is used to study its structural properties and explore as a fluorescent probe for metal ions. EPFC was investigated in terms of structural, fluorescence spectroscopic, UV-Vis spectroscopic and theoretical analysis by using HF/6-31G(d), CIS/6-31G(d) and B3LYP/6-31G(d) methods, respectively. The corresponding product was characterized by NMR and HRESIMS methods. The interactions of the compound with 15 kinds of metal ions (Pb2+, Mn2+, K+, Na+, Ag+, Ca2+, Cd2+, Co2+, Cu2+, Fe3+, Zn2+, Ni2+, Hg2+, Li+ and Mg2+) were investigated by UV absorption spectroscopy and fluorescence spectroscopy. The quantum chemical values suggested that it is easy for EPFC to lose electron with weak electron accepting ability by frontier molecular orbital analysis. The calculated spectra were complimented with experimental measurements in great degree. In addition, a novel rhodamine B derivative containing 1,2,3-triazole unit, and REPFC was successfully designed and synthesized by the reaction between rhodamine B and EPFC. REPFC displayed more selectivity response to Hg2+ ion than other metal ions in N,N-dimethylformamide (DMF)-H2O (V/V=1/1, pH 7.4) within a REPFC concentration range of 2.67×10-5~4.67×10-5 mol·L-1 with an fluorescent enhancement and a rapid chemical reaction. The triazole appended colorless chemosensor turns to pink upon complex formation only with Hg2+ions even in the presence of other common metal ions and enables naked-eye detection. The coordination mechanism and turn on/off fluorescence for Hg2+ ions were well proposed by explaining Hg2+ inducing the ring-opened rhodamine B moiety. This study was an advancement for the application of 1,2,3-triazole compound and provides guidance for using simple and high-selectivity Hg2+ probes in aqueous solutions under physiological conditions.
Li Jianling , Ding Guohua , Niu Yanyan , Wu Luyong , Duan Hongye , Feng Huajie , He Wenying . Structural Properties of Ethyl 5-Phenyl-2-(3-(trifluoromethyl)phenyl)-2H-1,2,3-triazole-4-carboxylate and Chromo Genic Responses of Its Rhodamine B Derivatives to Hg2+ Ions[J]. Chinese Journal of Organic Chemistry, 2018 , 38(4) : 931 -939 . DOI: 10.6023/cjoc201709001
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