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In Situ Synthesis of a Novel Quinone Imine Self‐Assembled Monolayer and Consideration of Its Reactivity with L ‐Arginine
Author(s) -
Hamzehloei Ali,
Mousavi Mir Fazlollah,
Bathaie S. Zahra
Publication year - 2012
Publication title -
electroanalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.574
H-Index - 128
eISSN - 1521-4109
pISSN - 1040-0397
DOI - 10.1002/elan.201200064
Subject(s) - imine , self assembled monolayer , chemistry , cyclic voltammetry , monolayer , quinone , fourier transform infrared spectroscopy , reactivity (psychology) , reaction rate constant , dielectric spectroscopy , covalent bond , electrochemistry , nucleophile , photochemistry , binding constant , polymer chemistry , electrode , stereochemistry , organic chemistry , kinetics , chemical engineering , catalysis , binding site , medicine , biochemistry , physics , alternative medicine , pathology , quantum mechanics , engineering
In situ functionalization of a 4‐aminothiophenol (4ATP) self‐assembled monolayer (SAM) on a Au electrode (4ATP/Au SAM) by the Michael addition reaction is considered. Under optimized conditions, the nucleophilic attack of the amino group of 4ATP/Au SAM to give an electrogenerated ortho ‐quinone produced a novel electroactive SAM (ESAM). The ESAM could be oxidized to quinone‐imine SAM (QI SAM) for the covalent immobilization of L ‐arginine monolayers. Cyclic voltammetry (CV), electrochemical impedance spectroscopy (EIS) and Fourier transform infrared (FTIR) spectroscopy are employed to characterize these systems.. The apparent heterogeneous rate constant ( k s app ) for ESAM/Au and the rate constant ( k ′) of the pseudo‐first order Michael addition reaction of L ‐arginine and ESAM/Au are calculated.