Versatile Supramolecular Gelators That Can Harden Water, Organic Solvents and Ionic Liquids

被引:86
作者
Minakuchi, Nami [1 ]
Hoe, Kazuki [1 ]
Yamaki, Daisuke [2 ]
Ten-no, Seiichiro [2 ]
Nakashima, Kazunori [1 ]
Goto, Masahiro [3 ]
Mizuhata, Minoru [1 ]
Maruyama, Tatsuo [1 ]
机构
[1] Kobe Univ, Dept Sci & Chem Engn, Nada Ku, Kobe, Hyogo 6578501, Japan
[2] Kobe Univ, Grad Sch Syst Informat, Nada Ku, Kobe, Hyogo 6578501, Japan
[3] Kyushu Univ, Ctr Future Chem, Grad Sch Engn, Dept Appl Chem, Fukuoka 8190395, Japan
关键词
MOLECULAR-WEIGHT GELATORS; PEPTIDE-AMPHIPHILE; L-VALINE; GELS; GELATION; MINERALIZATION; HYDROGELATORS; TRANSITION; SALTS;
D O I
10.1021/la301442f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
\We developed novel supramolecular gelators with simple molecular structures that could harden a broad range of solvents: aqueous solutions of a wide pH range, organic solvents, edible oil, biodiesel, and ionic liquids at gelation concentrations of 0.1-2 wt %. The supramolecular gelators were composed of a long hydrophobic tail, amino acids and gluconic acid, which were prepared by liquid-phase synthesis. Among seven types of the gelators synthesized, the gelators containing L-Val, L-Leu, and L-Ile exhibited high gelation ability to various solvents. These gelators were soluble in aqueous and organic solvents, and also in ionic liquids at high temperature. The gelation of these solvents was thermally reversible. The microscopic observations (TEM, SEM, and CLSM) and small-angle X-ray scattering (SAXS) measurements suggested that the gelator molecules self-assembled to form entangled nanofibers in a large variety of solvents, resulting in the gelation of these solvents. Molecular mechanics and density functional theory (DFT) calculations indicated the possible molecular packing of the gelator in the nanofibers. Interestingly, the gelation of an ionic liquid by our gelator did not affect the ionic conductivity of the ionic liquid, which would provide an advantage to electrochemical applications.
引用
收藏
页码:9259 / 9266
页数:8
相关论文
共 43 条
[31]   New L-valine-based hydrogelators: formation of supramolecular hydrogels [J].
Suzuki, M ;
Owa, S ;
Yumoto, M ;
Kimura, M ;
Shirai, H ;
Hanabusa, K .
TETRAHEDRON LETTERS, 2004, 45 (28) :5399-5402
[32]   Effects of hydrogen bonding and van der Waals interactions on organogelation using designed low-molecular-weight gelators and gel formation at room temperature [J].
Suzuki, M ;
Nakajima, Y ;
Yumoto, M ;
Kimura, M ;
Shirai, H ;
Hanabusa, K .
LANGMUIR, 2003, 19 (21) :8622-8624
[33]   Supramolecular organogel formation triggered by acid-base interaction in two-component system consisting of L-lysine derivative and aliphatic acids [J].
Suzuki, Masahiro ;
Saito, Hiroaki ;
Shirai, Hirofusa ;
Hanabusa, Kenji .
NEW JOURNAL OF CHEMISTRY, 2007, 31 (09) :1654-1660
[34]   Powerful low-molecular-weight gelators based on L-valine and L-isoleucine with various terminal groups [J].
Suzuki, Masahiro ;
Sato, Teruaki ;
Shirai, Hirofusa ;
Hanabusa, Kenji .
NEW JOURNAL OF CHEMISTRY, 2006, 30 (08) :1184-1191
[35]   Gels of ionic liquid [C4mim]PF6 formed by self-assembly of gelators and their electrochemical properties [J].
Tan, Lei ;
Dong, Xuelin ;
Wang, Hong ;
Yang, Yajiang .
ELECTROCHEMISTRY COMMUNICATIONS, 2009, 11 (05) :933-936
[36]   Responsive cyclohexane-based low-molecular-weight hydrogelators with modular architecture [J].
van Bommel, KJC ;
van der Pol, C ;
Muizebelt, I ;
Friggeri, A ;
Heeres, A ;
Meetsma, A ;
Feringa, BL ;
van Esch, J .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (13) :1663-1667
[37]   Smart amphiphiles:: hydro/organogelators for in situ reduction of gold [J].
Vemula, Praveen Kumar ;
John, George .
CHEMICAL COMMUNICATIONS, 2006, (21) :2218-2220
[38]   Synthesis and Characterization of Monosaccharide-Derived Carbamates as Low-Molecular-Weight Gelators [J].
Wang, Guijun ;
Cheuk, Sherwin ;
Yang, Hao ;
Goyal, Navneet ;
Reddy, P. V. Narasimha ;
Hopkinson, Branden .
LANGMUIR, 2009, 25 (15) :8696-8705
[39]   Glucose-Based Fluorescent Low-Molecular Mass Compounds: Creation of Simple and Versatile Supramolecular Gelators [J].
Yan, Ni ;
He, Gang ;
Zhang, Helan ;
Ding, Liping ;
Fang, Yu .
LANGMUIR, 2010, 26 (08) :5909-5917
[40]   Intracellular enzymatic formation of nanofibers results in hydrogelation and regulated cell death [J].
Yang, Zhimou ;
Xu, Keming ;
Guo, Zufeng ;
Guo, Zhihong ;
Xu, Bing .
ADVANCED MATERIALS, 2007, 19 (20) :3152-+