Release Time:2019-03-09  Hits:

Indexed by: Journal Article

Date of Publication: 2014-09-02

Journal: TETRAHEDRON

Included Journals: Scopus、SCIE

Volume: 70

Issue: 35

Page Number: 5872-5877

ISSN: 0040-4020

Key Words: ICT fluorophore; Skeletal characterization; Oxidative SNArH; 2D NMR; X-ray diffraction

Abstract: We have revisited the synthesis of a series of ICT fluorophores, which were reported to have a core structure of 8-oxo-8H-acenaphtho[1,2-b]pyrrol-9-carbonitrile. However, based on the 2D NMR and X-ray diffraction analysis, their core structure was corrected as 1-oxo-1H-phenalene-2,3-dicarbonitrile (1). Compound 1 shows a highly electron-deficient nature and can easily undergo oxidative SNArH reaction on the naphthyl ring to produce a series of novel ICT fluorophores. The regioselectivity of this substitution reaction was studied by introduction of representative nucleophiles. Moreover, due to the strong rigidity and efficient ICT nature, the obtained fluorescent dyes display very good spectroscopic properties even in an aqueous environment. (C) 2014 Elsevier Ltd. All rights reserved.