Electrochemical and Spectroelectrochemical Study of 7,7‘-Diapo-(7E,7‘Z)-diphenylcarotene

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Abstract

Self-assembled monolayers (SAMs) formed by adsorption of thiols onto gold provide a flexible method to study the electrochemical reactivity of 7,7‘-diapo-(7E,7‘Z)-diphenylcarotene (DDC) on such barrier monolayers. Barrier properties of three kinds of SAMs (long-chain n-alkanethiols, ω-substituted alkanethiols, and 4-mercaptopyridine) were investigated. The influence of the ω-functional group and the thickness (chain length in n-alkanethiols) of the monolayer on the electrochemical reaction of DDC was explored. Electron transfer between solution species and the modified-gold electrode can occur either by tunneling through the monolayer or by approaching the electrode at “pinholes” or defects in the monolayer. Compared to the behavior on bare gold electrodes, the thiol monolayers cause a barrier effect for the reaction of DDC and the adsorption of polymeric products on the Au electrode surface. With increasing chain length of alkanethiol molecules, a stronger barrier effect to the adsorption of polymeric products is observed. DDC and its electrochemical reaction products (including the radical cations and polymers) were also studied by simultaneous optical and electrochemical techniques.

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