Issue 6, 2001
From the journal:

Journal of Materials Chemistry

Frank Osterod,a   Lars Peters,a   Arno Kraft,*ab   Takeshi Sano,c   John J. Morrison,c   Neil Feederc  and  Andrew B. Holmes*c  

* Corresponding authors

a Institut für Organische Chemie und Makromolekulare Chemie II, Heinrich-Heine-Universität Düsseldorf, Universitätsstr. 1, Düsseldorf, Germany

b Department of Chemistry, Heriot-Watt University, Edinburgh, UK
E-mail: a.kraft@hw.ac.uk

c Melville Laboratory for Polymer Synthesis, Department of Chemistry, University of Cambridge, Pembroke Road, Cambridge, UK
E-mail: abh1@cam.ac.uk

Abstract

The synthesis of a number of stilbenecarboxylic acids, tetrazolylstilbenes and dithieno[3,2-b:2′,3′-d]thiophene-2-carboxylic acids is reported. These organic acids form non-covalent complexes with an imidazoline base, 1,3,5-tris(4,5-dihydroimidazol-2-yl)benzene 13. Two X-ray crystal structures confirm hydrogen bonds between carboxylate ligands and meta-positioned protonated imidazoline groups. The complexes possess a surprisingly flat disk-like shape with various close contacts between adjacent molecules. Most stilbene and dithieno[3,2-b:2′,3′-d]thiophene derivatives show strong blue or blue–green photoluminescence in solution, whereas fluorescence in the solid state is almost completely quenched.

Graphical abstract: Luminescent supramolecular assemblies based on hydrogen-bonded complexes of stilbenecarboxylic acids and dithieno[3,2-b:2′,3′-d]thiophene-2-carboxylic acids with a tris(imidazoline) base

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Article information

DOI
https://doi.org/10.1039/B009406O
Article type
Paper
Submitted
23 Nov 2000
Accepted
13 Mar 2001
First published
12 Apr 2001

J. Mater. Chem., 2001,11, 1625-1633

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Luminescent supramolecular assemblies based on hydrogen-bonded complexes of stilbenecarboxylic acids and dithieno[3,2-b:2′,3′-d]thiophene-2-carboxylic acids with a tris(imidazoline) base

F. Osterod, L. Peters, A. Kraft, T. Sano, J. J. Morrison, N. Feeder and A. B. Holmes, J. Mater. Chem., 2001, 11, 1625 DOI: 10.1039/B009406O

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