Issue 5, 2017

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
12 Jan 2017
Accepted
09 Feb 2017
First published
21 Feb 2017

Org. Chem. Front., 2017,4, 743-749

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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