Immobilization of Monolayers Incorporating Cu Funnel Complexes onto Gold Electrodes. Application to the Selective Electrochemical Recognition of Primary Alkylamines in Water

Gael De Leener; Ferdinand Evoung-Evoung; Angelique Lascaux; Jérémy Mertens; Ana Gabriela Porras-Gutierrez; Nicolas Le Poul; Corinne Lagrost; Diana Over; Yann R. Leroux; François Reniers; Philippe Hapiot; Yves Le Mest; Ivan Jabin; Olivia Reinaud

doi:10.1021/jacs.6b05317

Immobilization of Monolayers Incorporating Cu Funnel Complexes onto Gold Electrodes. Application to the Selective Electrochemical Recognition of Primary Alkylamines in Water

Gael De Leener ^{1, 2} Ferdinand Evoung-Evoung ³ Angelique Lascaux ¹ Jérémy Mertens ⁴ Ana Gabriela Porras-Gutierrez ³ Nicolas Le Poul ^{3, *} Corinne Lagrost ⁵ Diana Over ² Yann R. Leroux ⁵ François Reniers ⁴ Philippe Hapiot ⁵ Yves Le Mest ³ Ivan Jabin ^{1, *} Olivia Reinaud ^{2, *}

* Auteur correspondant

1 Laboratoire de Chimie Organique

2 LCBPT - UMR 8601 - Laboratoire de Chimie et de Biochimie Pharmacologiques et Toxicologiques

3 CEMCA - Chimie, Electrochimie Moléculaires et Chimie Analytique

4 Université libre de bruxelles, Service de chimie analytique et chimie des interfaces (CHANI)

5 ISCR - Institut des Sciences Chimiques de Rennes

Abstract : The immobilization of a copper calix[6]azacryptand funnel complex on gold-modified electrodes is reported. Two different methodologies are described. One is based on alkyne-terminated thiol self assembled monolayers. The other relies on the electrografting of a calix[4]arene platform bearing diazonium functionalities at its large rim and carboxylic functions at its small rim, which is post-functionalized with alkyne moieties. In both cases, the CuAAC electroclick methodology proved to be the method of choice for grafting the calix[6]azacryptand onto the monolayers. The surface-immobilized complex was fully characterized by surface spectroscopies and electrochemistry in organic and aqueous solvents. The Cu complex display a well-defined quasi-reversible system in cyclic voltammetry associated with the Cu(II)/Cu(I) redox process. Remarkably, this-redox process triggers a powerful selective detection of primary alkylamines in water at a micromolar level, based on a cavitary recognition process.

Keywords : self-assembled monolayers aliphatic-amines induced electroclick beta-cyclodextrin neutral molecules aqueous-solution metal-surfaces copper complex alkyl amines active-sites

Type de document :

Article dans une revue

Journal of the American Chemical Society, American Chemical Society, 2016, 138 (39), pp.12841--12853. 〈10.1021/jacs.6b05317〉

Domaine :

Chimie

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https://hal-univ-rennes1.archives-ouvertes.fr/hal-01395479
Contributeur : Laurent Jonchère <>
Soumis le : vendredi 9 décembre 2016 - 14:52:03
Dernière modification le : vendredi 4 janvier 2019 - 17:33:38
Document(s) archivé(s) le : jeudi 23 mars 2017 - 10:14:17

De Leener et al. - 2016 - Immo...

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Immobilization of Monolayers Incorporating Cu Funnel Complexes onto Gold Electrodes. Application to the Selective Electrochemical Recognition of Primary Alkylamines in Water

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Immobilization of Monolayers Incorporating Cu Funnel Complexes onto Gold Electrodes. Application to the Selective Electrochemical Recognition of Primary Alkylamines in Water

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