Synthesis and structural characterization of glucopyranosylamide films on gold.
Synthesis and structural characterization of glucopyranosylamide films on gold.
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DOI：
10.1021/la062678j
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发表时间：
2007-01
期刊：
影响因子：
--
通讯作者：
Mridula Kadalbajoo;Juhee Park;A. Opdahl;H. Suda;C. Kitchens;J. Garno;J. Batteas;M. Tarlov;P. DeShong
中科院分区：
文献类型：
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作者：
Mridula Kadalbajoo;Juhee Park;A. Opdahl;H. Suda;C. Kitchens;J. Garno;J. Batteas;M. Tarlov;P. DeShong
从α-和β-吡喃葡萄糖酰胺衍生物制备了葡萄糖衍生物在金表面的自组装单分子膜。通过原位生成葡糖基异恶唑啉，然后用硫代吡啶酯处理，立体选择性地合成葡糖基缀合物。用原子力显微镜、反射傅里叶变换红外光谱和X射线光电子能谱对薄膜结构进行了表征。实验数据表明，具有游离羟基的α-或β-连接的吡喃葡萄糖酰胺衍生物通过巯基连接体连接到金上。这两种衍生物形成具有高堆积密度的单层膜-与通常在金上观察到的烷醇单分子膜相当。这些共轭物的乙酸酯类似物不会在金上形成自组装膜;它们在相同的沉积条件下形成多层膜。
Self-assembled monolayers (SAMs) of glucose derivatives on gold have been prepared from alpha- and beta-glucopyranosylamide derivatives. The glucosyl conjugates were synthesized stereoselectively via the in situ generation of glucosyl isoxazolines followed by treatment with thiopyridyl esters. The resulting film structures were characterized by atomic force microscopy, reflection Fourier transform infrared spectroscopy, and X-ray photoelectron spectroscopy. The experimental data indicated that alpha- or beta-linked glucopyranosylamide derivatives with free hydroxyl groups attach to gold via the thiol linker. Both derivatives form monolayer films with high packing densities--comparable to those typically observed for alkanethiol monolayers on gold. Acetate analogues of these conjugates do not form SAMs on gold; they form multilayered films under identical deposition conditions.