Abstract

A new benzothiazole-based chemosensor BTN (1-((Z)-(((E)-3-methylbenzo[d]thiazol-2(3H)-ylidene)hydrazono)methyl)naphthalen-2-ol) was synthesized for the detection of Cu2+. BTN could detect Cu2+ with "off-on" fluorescent response from colorless to yellow irrespective of presence of other cations. Limit of detection for Cu2+ was determined to be 3.3μM. Binding ratio of BTN and Cu2+ turned out to be a 1:1 with the analysis of Job plot and ESI-MS. Sensing feature of Cu2+ by BTN was explained with theoretical calculations, which might be owing to internal charge transfer and chelation-enhanced fluorescence processes.

Highlights

  • Copper is one of the pivotal transition metals in human body [1,2,3]

  • Sensing feature of Cu2+ by BTN was explained with theoretical calculations, which might be owing to internal charge transfer and chelation-enhanced fluorescence processes

  • Compound BTN was produced by the coupling reaction between 2-hydroxy-1 naphthaldehyde and (E)-2hydrazono-3-methyl-2,3-dihydrobenzo[d]thiazole (Scheme 1)

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Summary

Introduction

Copper is one of the pivotal transition metals in human body [1,2,3]. It exists diverse enzymes like cytochrome oxidase and tyrosine, and plays an essential key role in vital metabolisms, such as redox system and physiological response [4]. A number of fluorescence chemosensors detecting Cu2+ have been developed because of the features such as great selectivity, versatility, sensitivity and relatively simple handling [9,10,11,12,13]. Fluorescence sensors which have “turn-on” system shows better sensing properties at their sensitivity, selectivity and easy observation than “turn-off” system [16,17,18]. The development of “turn-on” chemosensors for Cu2+ has been receiving substantial attention

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