An attempt to predict the gelation ability of hydrogen-bond-based gelators utilizing a glycoside library

被引:165
作者
Luboradzki, R
Gronwald, O
Ikeda, M
Shinkai, S
Reinhoudt, DN
机构
[1] Kyushu Univ, Grad Sch Engn, Dept Biochem & Chem, Fukuoka 8128581, Japan
[2] Japan Sci & Technol Corp, Chemotransfigurat Project, Kurume, Fukuoka 8390861, Japan
[3] Univ Twente, Fac Chem Technol, Chemotransfigurat Project, NL-7500 AE Enschede, Netherlands
[4] Polish Acad Sci, Inst Phys Chem, Warsaw, Poland
关键词
saccharides; organogels; X-ray crystal structure;
D O I
10.1016/S0040-4020(00)00915-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The correlation between the saccharide crystal structure and its gelating ability seems to be a useful tool for finding promising gelators. By analogy to the other types of the hydrogen-bond-based gelators the tendency to form one-dimensional hydrogen-bonded networks may he essential as a prerequisite for good gelators. The gelation abilities were tested for four configurational isomers (methyl-4,6 -O-benzylidyne-alpha -D-glucopyranoside, methyl-4,6-O-benzylidyne-alpha -D-allopyranoside, methyl-4,6-O-benzylidyne-alpha -D-altropyranoside, and methyl-4,6-O-benzylidyne-alpha -D-idopyranoside) which exhibit quite different hydrogen-bonded networks in their crystal structures. Only in the case of one-dimensional hydrogen-bonded architecture the good gel systems were found. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:9595 / 9599
页数:5
相关论文
共 56 条
[41]  
2-Z
[42]  
OTSUNI E, 1996, ANGEW CHEM INT EDIT, V35, P1324
[43]  
Richtmyer N.K., 1962, METHODS CARBOHYDR CH, V1, P107
[44]   CRYSTAL-STRUCTURES OF ALPHA-ANOMERS AND BETA-ANOMERS OF D-GALACTOSE [J].
SHELDRICK, B .
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1976, 32 (APR15) :1016-1020
[45]  
SOBNA JES, 1997, CHEM COMMUN, P327
[46]   FUNCTIONAL ORGANIC GELS - CHIRALITY INDUCTION THROUGH FORMATION OF HIGHLY-ORIENTED STRUCTURE [J].
TAKAFUJI, M ;
IHARA, H ;
HIRAYAMA, C ;
HACHISAKO, H ;
YAMADA, K .
LIQUID CRYSTALS, 1995, 18 (01) :97-99
[47]   STRUCTURES OF ORGANOGELS BASED UPON CHOLESTERYL 4-(2-ANTHRYLOXY)BUTANOATE, A HIGHLY EFFICIENT LUMINESCING GELATOR - NEUTRON AND X-RAY SMALL-ANGLE SCATTERING INVESTIGATIONS [J].
TERECH, P ;
FURMAN, I ;
WEISS, RG .
JOURNAL OF PHYSICAL CHEMISTRY, 1995, 99 (23) :9558-9566
[48]   Low molecular mass gelators of organic liquids and the properties of their gels [J].
Terech, P ;
Weiss, RG .
CHEMICAL REVIEWS, 1997, 97 (08) :3133-3159
[49]   Thermoreversible gelation of organic liquids by arylcyclohexanol derivatives: a structural study [J].
Terech, P ;
Allegraud, JJ ;
Garner, CM .
LANGMUIR, 1998, 14 (15) :3991-3998
[50]   Self-assembly of bisurea compounds in organic solvents and on solid substrates [J].
vanEsch, J ;
DeFeyter, S ;
Kellogg, RM ;
DeSchryver, F ;
Feringa, BL .
CHEMISTRY-A EUROPEAN JOURNAL, 1997, 3 (08) :1238-1243