Journal
LANGMUIR
Volume 33, Issue 13, Pages 3217-3222Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.langmuir.7b00300
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Funding
- Danish Council for Strategic Research [DA-GATE DSF 12-131827]
- Innovation Fund Denmark [Dreamwind 5152-00003B]
- Danish National Research Foundation [DNRF118]
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The reduction of an aryl iodide is generally believed to involve a clean-cut two-electron: reduction to produce an aryl anion and iodide. This is in contradiction to what is observed if a highly efficient grafting agent, such as an aryldiazonium salt, is employed. The difference in behavior is explained by the much more extreme potentials required for reducing an aryl iodide; which facilitates the further reduction of the aryl radical formed as an intermediate. However, in this study we disclose that electrografting of aryl iodides is indeed possible upon extended voltammetric cycling. This implies that even if the number of aryl radicals left unreduced at the electrode surface is exceedingly small, a functionalization of the surface may still be promoted. In fact,, the grafting efficiency is found to increase during the grafting process, which may be explained by the inhibiting effect the growing film exerts on the competing reduction of the aryl radical. The, slow buildup of the organic film results in a well-ordered structure as shown by the well-defined electrochemical response frond a grafted film containing ferrocenylmethyl groups. Hence, the reduction of aryl Iodides allows a precisely controlled, albeit slow, growth of thin organic films.
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