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

James Buttress, David Day, James Courtney, Elliot Lawrence, David Hughes, Robin Blagg, Alison Crossley, Susan Matthews, Carl Redshaw, Philip Bulman Page, Gregory Wildgoose

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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.
Original languageEnglish
Pages (from-to)7806–7813
JournalLangmuir
Volume32
Issue number31
Early online date15 Jul 2016
DOIs
Publication statusPublished - 9 Aug 2016

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