Synthesis of β‑Cyclodextrin Diazonium Salts and Electrochemical Immobilization onto Glassy Carbon and Gold Surfaces

Synthesis of β‑Cyclodextrin Diazonium Salts and Electrochemical Immobilization onto Glassy Carbon and Gold Surfaces

This study shows that diazotized β-cyclodextrin (β-CD) can be produced, isolated, and immobilized onto glassy carbon and gold surfaces. 4-(1,2,3-Triazol-4-yl)benzenediazonium-β-CD tetrafluoroborate (pDz-β-CD) and 3-(1,2,3-triazol-4-yl)benzenediazonium-β-CD tetrafluoroborate (mDz-β-CD) were successfu...

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Bibliographic Details
Published in:Langmuir Vol. 28; no. 49; pp. 16828 - 16833
Main Authors: Diget, Jakob Stensgaard, Petersen, Helga Nørgaard, Schaarup-Jensen, Henrik, Sørensen, Anders Ulrik, Nielsen, Thorbjørn Terndrup, Pedersen, Steen Uttrup, Daasbjerg, Kim, Larsen, Kim Lambertsen, Hinge, Mogens
Format: Journal Article
Language:English
Published: Washington, DC American Chemical Society 11-12-2012
Subjects:
Catalysis
Chemistry
Electrochemistry
Exact sciences and technology
General and physical chemistry
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
Polarization
Infrared reflection
Acetylenic compound
Infrared absorption
Immobilization
Metallocene
Chemical reduction
Cyclic voltammetry
Synthesis
Cavity
Nuclear magnetic resonance
Complexation
Gold
Intermediate product
Catalytic reaction
Hydrocarbon
Blocking
Transition metal
Carbon
Infrared spectrometry
Azides
Cyclodextrin
Electrochemistry
Aryl
Alkyne
Reflectance
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Summary:This study shows that diazotized β-cyclodextrin (β-CD) can be produced, isolated, and immobilized onto glassy carbon and gold surfaces. 4-(1,2,3-Triazol-4-yl)benzenediazonium-β-CD tetrafluoroborate (pDz-β-CD) and 3-(1,2,3-triazol-4-yl)benzenediazonium-β-CD tetrafluoroborate (mDz-β-CD) were successfully prepared by Cu(I)-catalyzed azide alkyne coupling (CuAAC) of 6-monodeoxy-6-monoazido-β-cyclodextrin (N3-β-CD) and 4-ethynylaniline and 3-ethynylaniline, respectively, followed by diazotization. The products were isolated and stored successfully for several months at −18 °C. The intermediates and products were verified by Attenuated Total Reflectance Fourier Transform Infrared, Nuclear Magnetic Resonance, and Heteronuclear Single Quantum Coherence. pDz-β-CD and mDz-β-CD were immobilized onto glassy carbon and gold surfaces facilitated by electrochemical reduction of the diazonium group. The thus generated aryl radical reacted with the surface. The modified gold surfaces were investigated by Polarization Modulation Infrared Reflection Absorption Spectroscopy and cyclic voltammetry employing the redox probe K3Fe(CN)6 to analyze the extent of blocking of the surfaces. Finally, the availability of the cavity of surface-immobilized β-CD was shown by complexation of ferrocene followed by cyclic voltametric analysis.
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ISSN:0743-7463
1520-5827
DOI:10.1021/la302329x