A new fluorophore displaying remarkable solvatofluorochromism and solid-state light emission, and serving as a turn-on fluorescent sensor for cyanide ions. Issue 5 (21st February 2017)

• Record Type: Journal Article
• Authors: Kimura, Yosuke; Kawajiri, Ikumi; Ueki, Masanori; Morimoto, Takayuki; Nishida, Jun-ichi; Ikeda, Hiroshi; Tanaka, Mirai; Kawase, Takeshi
• Is Part Of: Organic chemistry frontiers. Volume 4:Issue 5(2017)
• Page Start: 743
• Page End: 749
• Publication Date: 2017-02-21
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/c7qo00029d
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : A new fluorophore displays remarkable solvatofluorochromism, a CIEE effect, and an intense blue-green fluorescence in the presence of 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 [Δ λ EM = 170 nm (5060 cm −1 ) from cyclohexane to CH2 Cl2 ]. 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.