Issue 22, 2003
From the journal:

Organic & Biomolecular Chemistry

l-Lysine based gemini organogelators: their organogelation properties and thermally stable organogels

Masahiro Suzuki,*a   Tomomi Nigawara,b   Mariko Yumoto,b   Mutsumi Kimura,b   Hirofusa Shiraib  and  Kenji Hanabusaa  

* Corresponding authors

a Graduate School of Science and Technology, Shinshu University, Ueda, Nagano 386-8567, Japan
E-mail: msuzuki@giptc.shinshu-u.ac.jp

b Department of Functional Polymer Science, Faculty of Textile Science and Technology, Shinshu University, Ueda, Nagano 386-8567, Japan

Abstract

Novel gemini organogelators based on L-lysine, in which two L-lysine derivatives are linked by different alkylene chain lengths through the amide bond, have been simply and effectively synthesized, and their organogelation abilities and thermal stabilities have been investigated. In a series of L-lysine ethyl ester derivatives, the organogelation abilities decreased with increasing alkylene spacer length. In particular, bis(Nε-lauroyl-L-lysine ethyl ester) oxalyl amide is a good organogelator that gels most organic solvents such as alcohols, cyclic ethers, aromatic solvents and acetonitrile. Various oxalyl amide derivatives with different alkyl ester groups such as hexyl, decyl, dodecyl, 2-ethyl-1-hexyl and 3,5,5-trimethylhexyl also showed good organogelation abilities. Furthermore, it was found that the cyclohexane gels formed by some oxalyl amide derivatives have a high thermal stability.

Graphical abstract: l-Lysine based gemini organogelators: their organogelation properties and thermally stable organogels

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Article information

DOI
https://doi.org/10.1039/B308371C
Article type
Paper
Submitted
22 Jul 2003
Accepted
12 Sep 2003
First published
09 Oct 2003

Org. Biomol. Chem., 2003,1, 4124-4131

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L-Lysine based gemini organogelators: their organogelation properties and thermally stable organogels

M. Suzuki, T. Nigawara, M. Yumoto, M. Kimura, H. Shirai and K. Hanabusa, Org. Biomol. Chem., 2003, 1, 4124 DOI: 10.1039/B308371C

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