“Janus” Calixarenes: Double-Sided Molecular Linkers for Facile, Multianchor Point, Multifunctional, Surface Modification

Buttress, James, Day, David, Courtney, James, Lawrence, Elliot, Hughes, David, Blagg, Robin, Crossley, Alison, Matthews, Susan, Redshaw, Carl, Bulman Page, Philip and Wildgoose, Gregory (2016) “Janus” Calixarenes: Double-Sided Molecular Linkers for Facile, Multianchor Point, Multifunctional, Surface Modification. Langmuir, 32 (31). 7806–7813. ISSN 0743-7463

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Abstract

We herein report the synthesis of novel “Janus” calix[4]arenes bearing four “molecular tethering” functional groups on either the upper or lower rims of the calixarene. These enable facile multipoint covalent attachment to electrode surfaces with monolayer coverage. The other rim of the calixarenes bear either four azide or four ethynyl functional groups, which are easily modified by the copper(I)-catalyzed azide–alkyne cycloaddition reaction (CuAAC), either pre- or postsurface modification, enabling these conical, nanocavity reactor sites to be decorated with a wide range of substrates to impart desired chemical properties. Redox active species decorating the peripheral rim are shown to be electrically connected by the calixarene to the electrode surface in either “up” or “down” orientations of the calixarene.

Item Type: Article
Additional Information: ACS AuthorChoice - This is an open access article published under a Creative Commons Attribution (CC-BY) License, which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
Faculty \ School: Faculty of Science > School of Chemistry
Faculty of Science
Faculty of Science > School of Pharmacy
Depositing User: Pure Connector
Date Deposited: 24 Sep 2016 00:14
Last Modified: 31 Oct 2019 14:56
URI: https://ueaeprints.uea.ac.uk/id/eprint/59929
DOI: 10.1021/acs.langmuir.6b02222

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