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Synthesis and optical sensing properties of novel 1,2,3-triazolyl-benzothiazoles

Benzothiazole unit is an attractive building block in the design of novel fluorescent dyes because of its π-bridging and electron-withdrawing characteristics as well as high chemical and photophysical stability compared to other heteroaromatics. Introduction of different electron donating and/or electron-withdrawing substituents in the benzothiazole core can significantly affect the optical characteristics of the resulting molecule [1]. Click-derived 1, 2, 3-triazoles play important roles in sensing mechanisms as they can act as a covalent linkage between benzothiazole and a corresponding functional group or can directly participate in binding of the target analyte [2]. In this work we present the synthesis of novel benzothiazole-1, 2, 3-triazole conjugates using click-chemistry approach (Fig. 1a). The compounds are examined as potential chemosensing molecules in solutions using UV-vis absorption and fluorescence spectroscopy (Fig. 1b). To further investigate the potential use of these novel fluorophores in the design of sensing materials, paper test strips were prepared by drop casting the solution in CH2Cl2 and are examined as pH probes (Fig. 1c) as continuation of our ongoing research [3].

benzothiazole ; 1, 2, 3-triazole ; fluorescence ; chemosensor

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