Issue 4, 2013
From the journal:

New Journal of Chemistry

Synthesis of luminescent BPh2-coordinated 2-(2′-hydroxyphenyl)benzoxazole (HBO)†

Julien Massue,*a   Pascal Retailleau,b   Gilles Ulrich*a  and  Raymond Ziessel*a  

* Corresponding authors

a Laboratoire de Chimie Moléculaire et Spectroscopies Avancées (LCOSA), ICEES-LCOSA, UMR CNRS 7515, École Européenne de Chimie, Polymères et Matériaux (ECPM), 25 rue Becquerel, 67087 Strasbourg Cedex 02, France
E-mail: massue@unistra.fr, gulrich@unistra.fr, ziessel@unistra.fr

b Laboratoire de Cristallochimie, ICSN – CNRS Bât 27 – 1 avenue de la Terrasse, 91198 Gif-sur-Yvette Cedex, France

Abstract

Triphenylborane (BPh3) has been successfully coordinated to five π-conjugated aromatic systems containing a N∧O bidentate 2-(2′-hydroxyphenyl)benzoxazole (HBO) ligand. Complexes 6–8 are directly substituted on the phenolic side of the HBO core while the structure of derivatives 9–10 includes a 4-dibutylaminophenyl module linked through an ethynyl fragment, at position 4 or 5. The crystal structure of complexes 8 and 10 reveals different solid-state molecular packing depending on the substitution, a herringbone molecular packing being observed for complex 8 while the dibutylamino fragment present in complex 10 is in favour of a lamellar structure. The optical properties are highly dependent on the nature and the position of substituents. Solvatochromic charge-transfer emissions are observed for substitution at position 3 or 5 while singlet emission is favoured when position 4 is functionalized. Solid-state fluorescence reveals that complex 8 possesses red-shifted emission when dispersed in a KBr matrix.

Graphical abstract: Synthesis of luminescent BPh2-coordinated 2-(2′-hydroxyphenyl)benzoxazole (HBO)

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Article information

DOI
https://doi.org/10.1039/C3NJ41052H
Article type
Paper
Submitted
19 Nov 2012
Accepted
29 Jan 2013
First published
30 Jan 2013

New J. Chem., 2013,37, 1224-1230

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Synthesis of luminescent BPh2-coordinated 2-(2′-hydroxyphenyl)benzoxazole (HBO)

J. Massue, P. Retailleau, G. Ulrich and R. Ziessel, New J. Chem., 2013, 37, 1224 DOI: 10.1039/C3NJ41052H

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