Title

Electrochemical and infrared analysis of alkoxyaniline derivative monolayers on gold

Document Type

Article

Publication Date

12-1-2001

Abstract

Monolayers of 2-(6-mercaptohexan-1-oxy)aniline (AnC6SH) and 2-(7-mercaptoheptan-1-oxy)aniline (AnC7SH) on Au were characterized by reflection-absorption infrared (RAIR) spectroscopy and electrochemistry. Electrochemical oxidation of AnC6SH/Au and AnC7SH/Au in aqueous acidic solution leads to complex voltammetry indicative of oligomerization and degradation reactions of the aniline functionality. Scanning of the potential between 0.0 and +0.9 V vs. SSCE leads to four surface-confined redox waves occurring at +0.2, +0.4, +0.5, and +0.6 V vs. SSCE. The oxidized monolayers were found to display voltammetry equivalent in nature to that observed for poly(o-phenetidine), which exhibits redox waves for the leucoemeraldine/emeraldine (+0.2 V) and emeraldine/pernigraniline (+0.6 V) transformations and the formation of some quinonemonoimine degradation products (+0.4 V) in the polymer. A redox wave attributed to a quinonediimine dimer (+0.5 V) was also found for the oxidized monolayers. Further oxidation of this species leads to increased polymer production and degradation product formation. To reduce degradation product formation, AnC6SH/Au and AnC7SH/Au were oxidized in non-aqueous solution. This method led to production of only surface confined dimers as indicated by electrochemical analysis.

Publication Source (Journal or Book title)

ACS Symposium Series

First Page

306

Last Page

320

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