Issue 31, 2009
From the journal:

Journal of Materials Chemistry

Glycine-glutamic-acid-based organogelators and their fluoride anion responsive properties††

Mingjun Teng,a   Guichao Kuang,a   Xinru Jia,*a   Min Gao,a   Yan Lia  and  Yen Wei*b  

* Corresponding authors

a Beijing National Laboratory for Molecular Sciences, Key Laboratory of Polymer Chemistry and Physics of the Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing, China
E-mail: xrjia@pku.edu.cn
Fax: +86 10-62751708
Tel: +86 10-62752102

b Department of Chemistry, Drexel University, Philadelphia, USA
E-mail: weiyen@drexel.edu
Fax: +1 215 8952 650
Tel: +1 215 8951 265

Abstract

Novel low-molecular-weight organogelators (LMOGs) 1 and 2 derived from glycine-glutamic-acids (GGA) based dipeptide were synthesized. The difference on the chemical structures between 1 and 2 resulted in some interesting variations on their gelling behavior and fluoride anion (F−) responsive properties. Gelator 1 could gel aromatic solvents effectively, while gelator 2 possessed excellent gelation ability in protic solvents. Upon the addition of 0.5 equiv. F−, the toluene gel of 1 transformed into solution due to the disruption of the intermolecular hydrogen-bonding, whereas the alcohol gel of 2 was stable and preserved even by introducing 20 equiv. F−. Interestingly, 2 could be regarded as an efficient receptor for F− in acetonitrile (MeCN) solution. After the addition of F−, the fluorescent emission band of 2 red-shifted from 360 to 420 nm with the emission intensity enhanced drastically; the intensity of the CD signal decreased and almost disappeared after addition of 2 equiv. F−. These changes were due to the conformational change and hydrogen-bonding interaction between urea groups and F−. The results indicated that GGA-based 1 and 2 might represent potential sensor materials for the naked-eye detection of F−.

Graphical abstract: Glycine-glutamic-acid-based organogelators and their fluoride anion responsive properties

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Article information

DOI
https://doi.org/10.1039/B904263F
Article type
Paper
Submitted
03 Mar 2009
Accepted
15 May 2009
First published
23 Jun 2009

J. Mater. Chem., 2009,19, 5648-5654

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Glycine-glutamic-acid-based organogelators and their fluoride anion responsive properties

M. Teng, G. Kuang, X. Jia, M. Gao, Y. Li and Y. Wei, J. Mater. Chem., 2009, 19, 5648 DOI: 10.1039/B904263F

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