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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

par De Leener, Gaël ;Evoung, Ferdinand FE;Lascaux, Angélique ;Mertens, Jeremy ;Porras-Gutierrez, Ana Gabriela;Le Poul, Nicolas;Lagrost, Corinne;Over, Diana;Leroux, Yann;Reniers, François ;Hapiot, Philippe;Le Mest, Yves;Jabin, Ivan ;Reinaud, Olivia
Référence Journal of the American Chemical Society, 138, 39, page (12841-12853)
Publication Publié, 2016

Article révisé par les pairs

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Résumé :

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 postfunctionalized with alkyne moieties. In both cases, the CuAAC electroclick methodology revealed 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 displays a well-defined quasi-reversible system in cyclic voltammetry associated to the Cu(II)/Cu(I) redox process. Remarkably, this redox process triggers a powerful selective detection of primary alkylamines in water at micromolar level, based on a cavitary recognition process.