Covalently Anchored Carboxyphenyl Monolayer via Aryldiazonium Ion Grafting: A Well-Defined Reactive Tether Layer for On-Surface Chemistry
journal contributionposted on 24.06.2014, 00:00 by Lita Lee, Haifeng Ma, Paula A. Brooksby, Simon A. Brown, Yann R. Leroux, Philippe Hapiot, Alison J. Downard
Electrografting of aryl films to electrode surfaces from diazonium ion solutions is a widely used method for preparation of modified electrodes. In the absence of deliberate measures to limit film growth, the usual film structure is a loosely packed multilayer. For some applications, monolayer films are advantageous; our interest is in preparing well-defined monolayers of reactive tethers for further on-surface chemistry. Here, we describe the synthesis of an aryl diazonium salt with a protected carboxylic acid substituent. After electrografting to glassy carbon electrodes and subsequent deprotection, the layer is reacted with amine derivatives. Electrochemistry and atomic force microscopy are used to monitor the grafting, deprotection, and subsequent coupling steps. Attempts to follow the same procedures on gold surfaces suggest that the grafted layer is not stable in these reaction conditions.
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limit film growthelectrode surfacesmonolayer filmsreaction conditionsCovalently Anchored Carboxyphenyl Monolayergold surfacesaryl filmscarbon electrodesreactive tetherscarboxylic acid substituentfilm structurearyl diazonium saltforce microscopydeprotectionAryldiazonium Ion Graftingamine derivativesdiazonium ion solutions