Self-assembled monolayers of heptapodant ß-cyclodextrins on gold


Beulen, Marcel W.J. and Bugler, Jürgen and Lammerink, Ben and Geurts, Frank A.J. and Biemond, Ed M.E.F. and Leerdam, Kees G.C. and Veggel, Frank C.J.M. van and Engbersen, Johan F.J. and Reinhoudt, David N. (1998) Self-assembled monolayers of heptapodant ß-cyclodextrins on gold. Langmuir, 14 (22). pp. 6424-6429. ISSN 0743-7463

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Abstract:A route was developed for the synthesis of three different cyclodextrin adsorbates: heptakis{6-O-[3-(thiomethyl)propionyl)]-2,3-di-O-methyl}
-cyclodextrin, heptakis{6-O-[12-(thiododecyl)dodecanoyl)]-2,3-di-O-methyl}
-cyclodextrin (a short and long alkyl chain sulfide cyclodextrin adsorbate, respectively), and heptakis[6-deoxy-6-(3-mercaptopropionamidyl)-2,3-di-O-methyl]-ß-cyclodextrin (a short alkyl chain thiol adsorbate). Self-assembled monolayers on gold of these three cyclodextrin adsorbates with seven sulfur moieties were fully characterized by electrochemistry, wettability studies, X-ray photoelectron spectroscopy (XPS), and time-of-flight secondary ion mass spectrometry (TOF-SIMS). The electrochemical capacitance measurements show the differences between the thicknesses of the ß-cyclodextrin monolayers, and the XPS-(S2p) measurements show the different effectivenesses of the sulfur moieties of the three monolayers in their binding to the gold surface. Sulfide-based -cyclodextrin monolayers use on average 4.5 of the 7 attachment points whereas the thiol-based cyclodextrin monolayer only uses 3.2 of the 7 sulfurs. These experiments show that, for adsorbates with multiple attachment points, sulfides may be more effective than thiols. TOF-SIMS measurements confirm the robust attachment of these adsorbates on gold obtained by XPS.
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Copyright:© 1998 American Chemical Society
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Metis ID: 105983