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“Janus” calixarenes: double–sided molecular linkers for facile, multi-anchor point, multi-functional, surface modification

Buttress, James P.; Day, David P.; Courtney, James M.; Lawrence, Elliot J.; Hughes, David L.; Blagg, Robin J.; Crossley, Alison; Matthews, Susan E.; Redshaw, Carl; Page, Philip C. Bulman; Wildgoose, Gregory G.

Authors

James P. Buttress

David P. Day

James M. Courtney

Elliot J. Lawrence

David L. Hughes

Robin J. Blagg

Alison Crossley

Susan E. Matthews

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Professor Carl Redshaw C.Redshaw@hull.ac.uk
Professor of Inorganic Materials Chemistry and REF Lead for Chemistry

Philip C. Bulman Page

Gregory G. Wildgoose



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.

Citation

Buttress, J. P., Day, D. P., Courtney, J. M., Lawrence, E. J., Hughes, D. L., Blagg, R. J., …Wildgoose, G. G. (2016). “Janus” calixarenes: double–sided molecular linkers for facile, multi-anchor point, multi-functional, surface modification. Langmuir : the ACS journal of surfaces and colloids, 32(31), 7806-7813. https://doi.org/10.1021/acs.langmuir.6b02222

Journal Article Type Article
Acceptance Date Jul 14, 2016
Online Publication Date Jul 27, 2016
Publication Date Aug 9, 2016
Deposit Date Jul 27, 2016
Publicly Available Date Mar 29, 2024
Journal Langmuir
Print ISSN 0743-7463
Electronic ISSN 1520-5827
Publisher American Chemical Society
Peer Reviewed Peer Reviewed
Volume 32
Issue 31
Pages 7806-7813
DOI https://doi.org/10.1021/acs.langmuir.6b02222
Keywords “Janus” calixarenes
Public URL https://hull-repository.worktribe.com/output/441888
Publisher URL http://pubs.acs.org/doi/abs/10.1021/acs.langmuir.6b02222
Additional Information Copy of article first published in: Langmuir, 2016, v.32, issue 31

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