Issue 5, 2013
From the journal:

New Journal of Chemistry

Organogels from unsymmetrical π-conjugated 1,3,4-oxadiazole derivatives†

Chengxiao Zhao,a   Haitao Wang,a   Binglian Bai,b   Songnan Qu,c   Jianxi Song,a   Xia Ran,a   Yan Zhanga  and  Min Li*a  

* Corresponding authors

a Key Laboratory of Automobile Materials (Jilin University), Ministry of Education, Institute of Materials Science and Engineering, Jilin University, Changchun 130012, PR China
E-mail: minli@jlu.edu.cn

b College of Physics, Jilin University, Changchun 130012, PR China

c Key Laboratory of Excited State Processes, Changchun Institute of Optics, Fine Mechanics and Physics, Chinese Academy of Sciences, Changchun 130033, PR China

Abstract

In this study, the unsymmetrical π-conjugated gelators, 2-(3,4-bis(alkoxy)phenyl)-5-(pyridine-4-yl)-1,3,4-oxadiazole [4-POXD-Bn (n = 4, 8, 12)], were synthesized and screened for gelation in various solvents. The tendencies of the critical gelation concentration (CGC) and the gel–sol phase transition temperatures (Tgel) of the 4-POXD-B8 gels, as well as the relationship between the end-chain length of gelator and gelation ability, indicated that the solvophobic effect has a critical role in gelation. For the specific gelator that we studied, we observed that the strength of the solvophobic force was related to the solvent properties. The solvent effect on gelation was studied quantitatively using the solvent polarity parameters: polar solubility parameter (δa), dielectric constant (ε), and polarity parameter (ET(30)). The results revealed that the favorable δa domain and ET(30) domain for the gelation of 4-POXD-B8 was in the range of 8.1–12.6 (cal cm−3)1/2 and 43.3–55.7 kcal mol−1, respectively. Meanwhile, a decrease of δa and ET(30) in the solvents is unfavorable for gelation. Furthermore, the solvent effect on the microstructure of the gels was studied via scanning electron microscopy (SEM). The SEM images revealed that the gels from 4-POXD-B8 in DMSO and DMF were composed of helical ribbons, whereas those formed in other solvents consisted of flat ribbons.

Graphical abstract: Organogels from unsymmetrical π-conjugated 1,3,4-oxadiazole derivatives

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Article information

DOI
https://doi.org/10.1039/C3NJ40648B
Article type
Paper
Submitted
25 Jul 2012
Accepted
13 Feb 2013
First published
18 Feb 2013

New J. Chem., 2013,37, 1454-1460

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Organogels from unsymmetrical π-conjugated 1,3,4-oxadiazole derivatives

C. Zhao, H. Wang, B. Bai, S. Qu, J. Song, X. Ran, Y. Zhang and M. Li, New J. Chem., 2013, 37, 1454 DOI: 10.1039/C3NJ40648B

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