Controlled orientation of cyclodextrin derivatives immobilized on gold surfaces

被引:168
作者
Nelles, G [1 ]
Weisser, M [1 ]
Back, R [1 ]
Wohlfart, P [1 ]
Wenz, G [1 ]
MittlerNeher, S [1 ]
机构
[1] MAX PLANCK INST POLYMER RES,D-55128 MAINZ,GERMANY
关键词
D O I
10.1021/ja9539812
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Several different cyclodextrinthiol derivatives have been immobilized on gold surfaces through a chemisorption process to form films which exhibit significantly different features. Three monothiolated cyclodextrin derivatives with different spacers between the cyclodextrin cavity and the thiol group and a mixture of multithiolated cyclodextrins were synthesized and characterized. Chemisorption of these compounds onto gold surfaces gave films which were investigated by Fourier transform infrared (FTIR) spectroscopy, time-of-flight mass spectrometry, contact angle measurements, plasmon surface polariton (PSP) spectroscopy, and cyclic voltammetry. It was found that the chemical structure of each cyclodextrin derivative had a strong influence on the molecular architecture in the resulting films, and in particular on the orientation of the cyclodextrin torus. Models were developed to describe the molecular arrangement in the films.
引用
收藏
页码:5039 / 5046
页数:8
相关论文
共 51 条
[1]  
AKITO E, 1975, JPN KOKAI, V75, P520
[2]  
ARNDT T, 1988, THESIS U MAINZ GERMA
[3]  
ASHTON PR, 1991, ANGEW CHEM, V103, P96
[4]   FORMATION OF MONOLAYER FILMS BY THE SPONTANEOUS ASSEMBLY OF ORGANIC THIOLS FROM SOLUTION ONTO GOLD [J].
BAIN, CD ;
TROUGHTON, EB ;
TAO, YT ;
EVALL, J ;
WHITESIDES, GM ;
NUZZO, RG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (01) :321-335
[5]   CONFORMATION OF O-METHYLATED AMYLOSE AND CYCLODEXTRINS [J].
CASU, B ;
REGGIANI, M ;
GALLO, GG ;
VIGEVANI, A .
TETRAHEDRON, 1968, 24 (02) :803-&
[6]  
CHUNG C, 1990, THESIS IOWA STATE U
[7]   PROTECTION OF HYDROXYL GROUPS AS TERT-BUTYLDIMETHYLSILYL DERIVATIVES [J].
COREY, EJ ;
VENKATESWARLU, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (17) :6190-+
[9]   SYNTHESIS, STRUCTURE, AND PROPERTIES OF MODEL ORGANIC-SURFACES [J].
DUBOIS, LH ;
NUZZO, RG .
ANNUAL REVIEW OF PHYSICAL CHEMISTRY, 1992, 43 :437-463
[10]   BLOCKING ORIENTED MONOLAYERS OF ALKYL MERCAPTANS ON GOLD ELECTRODES [J].
FINKLEA, HO ;
AVERY, S ;
LYNCH, M ;
FURTSCH, T .
LANGMUIR, 1987, 3 (03) :409-413