Rational Design and Facile Synthesis of Dual-State Emission Fluorophores: Expanding Functionality for the Sensitive Detection of Nitroaromatic Compounds |
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| Authors: | Dr. Si-Hong Chen Dr. Shi-He Luo Dr. Long-Jiang Xing Dr. Kai Jiang Yan-Ping Huo Qi Chen Prof. Zhao-Yang Wang |
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| Affiliation: | 1. School of Chemistry, South China Normal University, Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, Guangzhou Key Laboratory of Analytical Chemistry for Biomedicine, Guangzhou, 510006 P. R. China;2. School of Chemical Engineering & Light Industry, Guangdong University of Technology, Guangzhou, 510006 P. R. China;3. Key Laboratory of Functional Molecular Engineering of Guangdong Province, South China University of Technology, Guangzhou, 510640 P. R. China |
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| Abstract: | Six novel benzimidazole-based D-π-A compounds 4 a – 4 f were concisely synthesized by attaching different donor/acceptor units to the skeleton of 1,3-bis(1H-benzimidazol-2-yl)benzene on its 5-position through an ethynyl link. Due to the twisted conformation and effective conjugation structure, these dual-state emission (DSE) molecules show intense and multifarious photoluminescence, and their fluorescence quantum yields in solution and solid state can be up to 96.16 and 69.82 %, respectively. Especially, for excellent photostability, obvious solvatofluorochromic and extraordinary wide range of solvent compatibility, DSE molecule 4 a is a multifunctional fluorescent probe for the visual detection of nitroaromatic compounds (NACs) with the limit of detection as low as 10−7 M. The quenching mechanism has been proved as the results of photoinduced electron transfer and fluorescence resonance energy transfer processes. Importantly, probe 4 a can sensitively detect NACs not only in real water samples, but also on 4 a -coated strips and 4 a @PBAT thin films. |
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| Keywords: | benzimidazole fluorophores dual-state emission D-π-A systems ICT effects NACs detection |
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