Two benzothiadiazole-based compounds as multifunctional fluorescent sensors for detection of organic amines and anions

• Published in: Polyhedron Vol. 199; pp. 115100 - 115109
• Main Authors: Qiu, Cheng-Qiang, Li, Le-Qian, Yao, Shu-Li, Liu, Sui-Jun, Xu, Hui, Zheng, Teng-Fei
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 01.05.2021; Elsevier
• Subjects: Benzothiadiazole-based compounds; Chemistry; Chemistry, Inorganic & Nuclear; Crystallography; Fluorescence sensors; Hypochlorite; N,N,N’,N’-tetramethylethylenediamine; Physical Sciences; Science & Technology; Triethylamine; Benzothiadiazole-based compounds; N,N,N’,N’-tetramethylethylenediamine; Hypochlorite; Fluorescence sensors; Triethylamine; CHEMOSENSOR; COMPLEX; N,N,N ',N '-tetramethylethylenediamine; ACID; FRAMEWORKS; PROBES
• ISSN: 0277-5387; 1873-3719
• DOI: 10.1016/j.poly.2021.115100

Two benzothiadiazole-based compounds have been prepared as multifunctional fluorescence sensors to detect TEA and TMEDA, and compound 1 can also recognize EDA, MnO4− and ClO−. Compounds 1 and 2 are the first fluorescent sensors that selectively recognize TMEDA. [Display omitted] Two benzothiadiazole-based compounds, namely 4,7-di(1H-1,2,4-triazol-1-yl)benzo-[2,1,3]thiadiazole (1) and 4,7-di(1H-pyrazol-1-yl)benzo-[2,1,3]thiadiazole (2), have been constructed with Cu-catalyzed cross-coupling reactions. The fluorescence studies show that compound 1 has high selectivity and sensitivity toward TEA (triethylamine), EDA (ethylenediamine), TMEDA (N,N,N’,N’-tetramethylethylenediamine), MnO4− and ClO− by fluorescence quenching, and compound 2 also has high selectivity and sensitivity toward TEA and TMEDA via fluorescence quenching. The calculated detection limits of 1 for TEA, EDA, TMEDA, MnO4− and ClO− are 0.129, 0.635, 0.320, 9.820 and 12.740 μM, respectively. Meanwhile, the detection limits of compound 2 for TEA and TMEDA are 0.400 and 0.278 μM, respectively. Interestingly, compounds 1 and 2 are the first fluorescent sensors for the selective recognition of TMEDA.