1. 'Janus' Calixarenes: double-sided molecular linkers for facile, multianchor point, multifunctional, surface modification
- Author
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David P. Day, Elliot J. Lawrence, Susan E. Matthews, Gregory G. Wildgoose, Philip C. Bulman Page, Alison Crossley, James M. Courtney, Robin J. Blagg, David L. Hughes, Carl Redshaw, and James P. Buttress
- Subjects
Chemistry ,02 engineering and technology ,Surfaces and Interfaces ,010402 general chemistry ,021001 nanoscience & nanotechnology ,Condensed Matter Physics ,01 natural sciences ,Combinatorial chemistry ,Cycloaddition ,0104 chemical sciences ,chemistry.chemical_compound ,Covalent bond ,Electrode ,Calixarene ,Monolayer ,Electrochemistry ,Organic chemistry ,Surface modification ,General Materials Science ,Janus ,Azide ,Interfaces: Adsorption, Reactions, Films, Forces, Measurement Techniques, Charge Transfer, Electrochemistry, Electrocatalysis, Energy Production and Storage ,0210 nano-technology ,Spectroscopy - 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.
- Published
- 2016