Issue 7, 2016

2,4 and 2,5-bis(benzooxazol-2′-yl)hydroquinone (DHBO) and their borate complexes: synthesis and optical properties

Abstract

This article describes the multistep synthesis and the solution/solid-state optical properties of a series of highly fluorescent dyes based on either a 2,4 or a 2,5-bis(benzooxazol-2′-yl)hydroquinone (DHBO) scaffold. Their fluorescence emission stems from an intrinsic excited-state intramolecular proton transfer (ESIPT) photophysical process, which is highly dependent on the environment of the probe (solvent/matrix). Besides their ESIPT emission, these dyes are also excellent chelates towards boron(III) fragments such as BF2 or B(Ar)2 leading to singlet emitters with a quantum yield in solution reaching up to 51%. The solid-state emission of all these fluorophores was investigated by dispersing them as pellets in a KBr matrix revealing an intense emission in condensed matter.

Graphical abstract: 2,4 and 2,5-bis(benzooxazol-2′-yl)hydroquinone (DHBO) and their borate complexes: synthesis and optical properties

Supplementary files

Article information

Article type
Paper
Submitted
12 Jan 2016
Accepted
20 Apr 2016
First published
21 Apr 2016

New J. Chem., 2016,40, 5877-5884

2,4 and 2,5-bis(benzooxazol-2′-yl)hydroquinone (DHBO) and their borate complexes: synthesis and optical properties

K. Benelhadj, J. Massue and G. Ulrich, New J. Chem., 2016, 40, 5877 DOI: 10.1039/C6NJ00113K

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