Synthesis and structural characterization of glucopyranosylamide films on gold. Academic Article

abstract

• 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.

authors

• Batteas, James

published proceedings

• Langmuir

author list (cited authors)

• Kadalbajoo, M., Park, J., Opdahl, A., Suda, H., Kitchens, C. A., Garno, J. C., ... DeShong, P.

citation count

• 13

complete list of authors

• Kadalbajoo, Mridula||Park, Juhee||Opdahl, Aric||Suda, Hiromi||Kitchens, Carolyn A||Garno, Jayne C||Batteas, James D||Tarlov, Michael J||DeShong, Philip

publication date

• January 2007

publisher

• American Chemical Society (ACS)  Publisher

published in

• Langmuir  Journal

keywords

• Adsorption
• Amides
• Chemistry, Physical
• Disulfides
• Glucosides
• Gold
• Microscopy, Atomic Force
• Microscopy, Scanning Probe
• Models, Chemical
• Molecular Conformation
• Solvents
• Spectrometry, X-ray Emission
• Spectroscopy, Fourier Transform Infrared
• Surface Properties

PubMed Central ID

• 17209623

Digital Object Identifier (DOI)

• 10.1021/la062678j

start page

• 700

end page

• 707

volume

• 23

issue

• 2

URL

• http://dx.doi.org/10.1021/la062678j