Stereochemical effect of even-odd connecting links on supramolecular assemblies made of 1-glucosamide bolaamphiphiles

被引:231
作者
Shimizu, T
Masuda, M
机构
[1] Department of Organic Materials, Natl. Inst. of Mat. and Chem. Res., Tsukuba, Ibaraki 305
关键词
D O I
10.1021/ja961226y
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Bolaamphiphiles with a 1-glucosamide-head group at each end, N,N'-bis(beta-D-glucopyranosyl)alkane-1, n-dicarboxamide [Glc-NC(n)CN-Glc, n=6, 9, 10, 11, 12, 13, and 14], have been synthesized. Self-assembled supramolecular structures in water strongly depend on whether a is even or odd, which respectively give rise to fibrous assemblies or planar platelets as well as amorphous solids. In connection with this even-odd effect of the hydrocarbon links, internal molecular arrangements of the solid fibers were investigated using FT-IR spectroscopy, X-ray diffraction and crystal analyses, and transmission electron microscopy. The oligomethylene groups of the Glc-NC(12)CN-Glc pack in a monoclinic or an orthorhombic mode in the fiber. We propose a possible self-assembled model based on a monolayer sheet, which is stabilized by hydrogen-bond networks via sugar-head and amide groups.
引用
收藏
页码:2812 / 2818
页数:7
相关论文
共 42 条
[1]   MONOMOLECULAR LEAFLETS OF 2,8,12,18-TETRAETHYL-3,7,13,17-TETRAPYRIDIN-4-YLPORPHYRIN IN BULK AQUEOUS-MEDIA [J].
ENDISCH, C ;
BOTTCHER, C ;
FUHRHOP, JH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (31) :8273-8274
[2]   SUPRAMOLECULAR ASSEMBLIES OF DIACETYLENIC ALDONAMIDES [J].
FRANKEL, DA ;
OBRIEN, DF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (22) :10057-10069
[3]   LIPID BILAYER FIBERS FROM DIASTEREOMERIC AND ENANTIOMERIC N-OCTYLALDONAMIDES [J].
FUHRHOP, JH ;
SCHNIEDER, P ;
BOEKEMA, E ;
HELFRICH, W .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (09) :2861-2867
[4]   FLUID AND SOLID FIBERS MADE OF LIPID MOLECULAR BILAYERS [J].
FUHRHOP, JH ;
HELFRICH, W .
CHEMICAL REVIEWS, 1993, 93 (04) :1565-1582
[5]   THE CHIRAL BILAYER EFFECT STABILIZES MICELLAR FIBERS [J].
FUHRHOP, JH ;
SCHNIEDER, P ;
ROSENBERG, J ;
BOEKEMA, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (11) :3387-3390
[6]   CLOTH-LIKE AGGREGATES OF MICELLAR FIBERS MADE OF N-DODECYLTARTARIC ACID MONOAMIDES [J].
FUHRHOP, JH ;
DEMOULIN, C ;
ROSENBERG, J ;
BOETTCHER, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (07) :2827-2829
[7]   MOLECULAR MONOLAYER RODS AND TUBULES MADE OF ALPHA-(L-LYSINE),OMEGA-(AMINO) BOLAAMPHIPHILES [J].
FUHRHOP, JH ;
SPIROSKI, D ;
BOETTCHER, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (04) :1600-1601
[8]  
FUHRHOP JH, 1994, MEMBRANES MOL ASSEMB
[9]  
Goto M., 1970, Journal of Japan Oil Chemists' Society [Yukagaku], V19, P583
[10]   CRYSTAL-STRUCTURE OF B-FORM OF STEARIC-ACID [J].
GOTO, M ;
ASADA, E .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1978, 51 (09) :2456-2459