title: Electrochemical release of amine molecules from carbamate-based, electroactive self-assembled monolayers.
abstract: In this paper, carbamate-based self-assembled monolayers (SAMs) of alkanethiolates on gold were suggested as a versatile platform for release of amine-bearing molecules in response to the electrical signal. The designed SAMs underwent the electrochemical oxidation on the gold surface with simultaneous release of the amine molecules. The synthesis of the thiol compounds was achieved by coupling isocyanate-containing compounds with hydroquinone. The electroactive thiol was mixed with 11-mercaptoundecanol [HS(CH(2))(11)OH] to form a mixed monolayer, and cyclic votammetry was used for the characterization of the release behaviors. The mixed SAMs showed a first oxidation peak at +540 mV (versus Ag/AgCl reference electrode), indicating the irreversible conversion from carbamate to hydroquinone groups with simultaneous release of the amine molecules. The analysis of ToF-SIMS further indicated that the electrochemical reaction on the gold surface successfully released amine molecules.
authors: Molecular-Level Interface Research Center, Department of Chemistry, KAIST, Daejeon 305-701, Korea.
authors: Daewha
authors: D
authors: Hong
authors: Kyungtae
authors: K
authors: Kang
authors: Seok-Pyo
authors: SP
authors: Hong
authors: Hyun Kyong
authors: HK
authors: Shon
authors: Jin Gyeong
authors: JG
authors: Son
authors: Tae Geol
authors: TG
authors: Lee
authors: Insung S
authors: IS
authors: Choi
mesh_terms: D000588:Amines / Q000737:chemistry*; D002219:Carbamates / Q000737:chemistry*; D004563:Electrochemistry / Q000379:methods*; D006046:Gold; D010084:Oxidation-Reduction; D018629:Spectrometry, Mass, Secondary Ion
chemical_list: D000588:Amines; D002219:Carbamates; D006046:Gold