Benzothiazole applications as fluorescent probes for analyte detection

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Benzothiazole applications as fluorescent probes for analyte detection Fanyong Yan1 · Jingru Sun1 · Yueyan Zang1 · Zhonghui Sun1 · Hao Zhang1 · Xiang Wang1 Received: 3 May 2020 / Accepted: 6 July 2020 © Iranian Chemical Society 2020

Abstract  The introduction of certain structures or functional groups on benzothiazole and its derivatives containing a benzene ring and a thiazole ring can be used to construct benzothiazole fluorescent probes. Based on the mechanism of photoinduced electron transfer, excited-state intramolecular proton transfer (ESIPT), intramolecular charge transfer, aggregation-induced emission, the obtained fluorescent probes can specifically interact with the analyte, thereby changing their luminescence characteristics to achieve the detection of the analyte. Benzothiazole fluorescent probes can be applied to the detection of substances, the analysis of harmful substances and cell imaging. In this paper, the research situation of benzothiazole fluorescent probes in the past 5 years is reviewed, and it is mainly divided into metal ions, anions, small molecules and biological macromolecules according to the types of analytes. In the conclusion, the current challenges and further applications of benzothiazole fluorescent probes are analyzed. Graphic abstract Application of detection and analysis of benzothiazole fluorescent probes.

Keywords  Benzothiazole · Fluorescent probe · Limit of detection · Detection · Application

* Fanyong Yan [email protected] Extended author information available on the last page of the article

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Introduction Benzothiazole and its derivatives are important heterocyclic compounds and are used in various chemical fields due to their rigid conjugated structure, good optical properties and pharmacological activity, for example, for the construction of fluorescent probes, scale inhibitors and functional molecules, dyes, drugs, sensors, etc., which are widely used to construct fluorescent probes [1]. Fluorescent probes have been developed rapidly in the past decade. Compared with traditional analytical techniques, such as titration, chromatography, electrochemistry and chemiluminescence, fluorescent probes can achieve specific detection and rapid response to analytes [2]. The benzothiazole fluorescent probe has the advantages of high quantum yield and large Stokes shift. It is mainly composed of two parts: the benzothiazole moiety, namely the R1 moiety and the R ­ 2 moiety connected to the benzothiazole. The benzothiazole moiety is mainly prepared by the condensation reaction of 2-aminothiophenol such as the condensation reaction using N ­ H3(CH2)7NH3BiCl5 as the catalyst, the cyclization reaction of thioformanilides or thiourea, the catalytic addition reaction of o-haloaniline and a sulfur-containing compound, and the C–C coupling reaction at the 2-position of the benzothiazole [3]. ­R2 represents a small organic molecule connected to benzothiazole part through a carbon–carbon double bond, a carbon–nitrogen double bond, aniline, pheno