Supramolecular gels formed by amphiphilic low-molecular-weight gelators of Nα,Nε-diacyl-L-lysine derivatives

被引：82

作者：

Suzuki, M. ^{[1
]}

Yumoto, M. ^{[1
]}

Shirai, H. ^{[1
]}

Hanabusa, K. ^{[1
]}

机构：

[1] Shinshu Univ, Grad Sch Sci & Technol, Nagano 3868567, Japan

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2008年 / 14卷 / 07期

关键词：

gels; lysine; nanostructures; sol-gel processes; supramolecular chemistry;

D O I：

10.1002/chem.200701111

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Simple L-lysine derivatives, N-alpha-hexanoyl-N-epsilon-Iauroyl-L-lysine (1), its alkali metal salts (2-A), and two-component compounds that consist of 1 with 2 to 4, were synthesized and their hydrogelation and organogelation properties were studied. Addition of hydrochloric acid to an aqueous solution of the alkali metal salt at room temperature produced a translucent hydrogel. This hydrogelation occurred as a result of a change in nanostructure from micelle-like aggregates to nanofibers, which was induced by partial protonation of the carboxylate to form a carboxylic acid. On the other hand, two-component low-molecular-weight gelators exhibited amphiphilic gelation behavior and functioned as not only hydrogelators, but also as organogelators. FTIR studies revealed that lateral ionic interactions between the carbdxylate, alkali metal cation, carboxylic acid, and protons, in addition to hydrogen-bonding and van der Waals interactions play a very important role in hydrogelation. Furthermore, it was found that the water-insoluble carboxylic acid compound underwent a precipitation-dissolution transition with a thermally reversible sol-gel transition in the two-component gelator systems.

引用

页码：2133 / 2144

页数：12

共 109 条

[21] Controlled synthesis of double- and multiwall silver nanotubes with template organogel from a bolaamphiphile [J].

Gao, P ;

Zhan, CL ;

Liu, MH .

LANGMUIR, 2006, 22 (02) :775-779

[22] Gelation of perfluorinated liquids by N-alkyl perfluoroalkanamides [J].

George, M ;

Snyder, SL ;

Terech, P ;

Weiss, RG .

LANGMUIR, 2005, 21 (22) :9970-9977

[23] Primary alkyl amines as latent gelators and their organogel adducts with neutral triatomic molecules [J].

George, M ;

Weiss, RG .

LANGMUIR, 2003, 19 (04) :1017-1025

[24] Molecular organogels. Soft matter comprised of low-molecular-mass organic gelators and organic liquids [J].

George, Mathew ;

Weiss, Richard G. .

ACCOUNTS OF CHEMICAL RESEARCH, 2006, 39 (08) :489-497

[25] Preparation of metal oxide nanotubes using gelators as structure-directing agents [J].

Hanabusa, K ;

Numazawa, T ;

Kobayashi, S ;

Suzuki, M ;

Shirai, H .

MACROMOLECULAR SYMPOSIA, 2006, 235 :52-56

[26] 2-COMPONENT, SMALL-MOLECULE GELLING AGENTS [J].

HANABUSA, K ;

MIKI, T ;

TAGUCHI, Y ;

KOYAMA, T ;

SHIRAI, H .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (18) :1382-1384

[27] Easy preparation and useful character of organogel electrolytes based on low molecular weight gelator [J].

Hanabusa, K ;

Hiratsuka, K ;

Kimura, M ;

Shirai, H .

CHEMISTRY OF MATERIALS, 1999, 11 (03) :649-655

[28] Self-assembly and mineralization of peptide-amphiphile nanofibers [J].

Hartgerink, JD ;

Beniash, E ;

Stupp, SI .

SCIENCE, 2001, 294 (5547) :1684-1688

[29] Orthogonal self-assembly of low molecular weight hydrogelators and surfactants [J].

Heeres, A ;

van der Pol, C ;

Stuart, MCA ;

Friggeri, A ;

Feringa, BL ;

van Esch, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (47) :14252-14253

[30] Two-component gel-phase materials - Highly tunable self-assembling systems [J].

Hirst, AR ;

Smith, DK .

CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (19) :5496-5508

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