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Issue 5, 2017
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A new fluorophore displaying remarkable solvatofluorochromism and solid-state light emission, and serving as a turn-on fluorescent sensor for cyanide ions

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Abstract

A new tetrabenzofluorene fluorophore, containing 2,2-dicyanoethenylphenyl groups, was synthesized and subjected to photophysical studies. This substance was found to exhibit a relatively intense fluorescence in various organic solvents associated with remarkable solvatofluorochromism [ΔλEM = 170 nm (5060 cm−1) from cyclohexane to CH2Cl2]. In addition, the tetrabenzofluorene derivative displays crystallization-induced enhanced emission (CIEE) in aqueous THF solutions. The results of theoretical calculations show that this substance has a low energy LUMO and that a high level of spatial separation exists between its HOMO and LUMO. This finding suggests that the ground-to-excited state electronic transition of this substance should have intramolecular charge-transfer character. In addition, the tetrabenzofluorene derivative serves as a turn-on fluorescent sensor for cyanide by displaying an intense blue-green fluorescence in the presence of cyanide ions.

Graphical abstract: A new fluorophore displaying remarkable solvatofluorochromism and solid-state light emission, and serving as a turn-on fluorescent sensor for cyanide ions

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Publication details

The article was received on 12 Jan 2017, accepted on 09 Feb 2017 and first published on 21 Feb 2017


Article type: Research Article
DOI: 10.1039/C7QO00029D
Citation: Org. Chem. Front., 2017,4, 743-749
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    A new fluorophore displaying remarkable solvatofluorochromism and solid-state light emission, and serving as a turn-on fluorescent sensor for cyanide ions

    Y. Kimura, I. Kawajiri, M. Ueki, T. Morimoto, J. Nishida, H. Ikeda, M. Tanaka and T. Kawase, Org. Chem. Front., 2017, 4, 743
    DOI: 10.1039/C7QO00029D

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