Issue 19, 2003
From the journal:

Organic & Biomolecular Chemistry

A new urea gelator: incorporation of intra- and intermolecular hydrogen bonding for stable 1D self-assembly

Kazuhiro Yabuuchi,a   Emmanuel Marfo-Owusua  and  Takashi Kato*a  

* Corresponding authors

a Department of Chemistry and Biotechnology, School of Engineering, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-8656, Japan
E-mail: kato@chiral.t.u-tokyo.ac.jp
Fax: +81 3 5841 8661
Tel: +81 3 5841 7440

Abstract

A new bisurea gelator derived from 2,6-diaminopyridine has been developed. It efficiently gelates common organic and liquid crystalline (LC) solvents by forming elongated self-assembled fibres in solvents. X-Ray crystallography and 1H NMR measurements reveal that two urea groups in pyridine-based bisurea compounds form different hydrogen bonding patterns. One of two urea units is involved in intramolecular hydrogen bonding with the pyridyl nitrogen, while the other urea unit forms bifurcated intermolecular hydrogen bonding. This hydrogen-bonded structure is key for the fibrous self-assembly along with the efficient gelation. In addition, LC gels based on the pyridine-based gelator exhibit good electrooptic properties. These results indicate that the pyridine-based bisurea compound is a good gelator not only effective in gelation but also useful as a component of functional soft materials.

Graphical abstract: A new urea gelator: incorporation of intra- and intermolecular hydrogen bonding for stable 1D self-assembly

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Article information

DOI
https://doi.org/10.1039/B307149A
Article type
Paper
Submitted
26 Jun 2003
Accepted
14 Aug 2003
First published
27 Aug 2003

Org. Biomol. Chem., 2003,1, 3464-3469

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A new urea gelator: incorporation of intra- and intermolecular hydrogen bonding for stable 1D self-assembly

K. Yabuuchi, E. Marfo-Owusu and T. Kato, Org. Biomol. Chem., 2003, 1, 3464 DOI: 10.1039/B307149A

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