“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.

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., Crossley, A., Matthews, S. E., Redshaw, C., Page, P. C. B., & 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: Jul 27, 2016
• Journal: Langmuir
• Print ISSN: 0743-7463
• 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
• Contract Date: Jul 27, 2016