Pyrene-anchored boronic acid receptors on carbon nanoparticle supports: Fluxionality and pore effects

Katherine Lawrence, Tomoki Nishimura, Peter Haffenden, John M. Mitchels, Kazuo Sakurai, John S. Fossey, Steven D. Bull, Tony D. James, Frank Marken

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

Pyrene-appended boronic acids self-assemble onto graphitic surfaces and are shown here to self-assemble also around negatively charged carbon nanoparticles of ca. 8-18 nm diameter (Emperor 2000, Cabot Corp.). The resulting boronic acid modified nanoparticles are water-insoluble and readily deposited onto graphite electrodes, for example for electroanalytical applications. Boronic acid binding to the ortho-quinol caffeic acid is demonstrated and the mechanism based on ligand fluxionality is further investigated. Electrodes based on nanoparticle aggregates are sensitive to caffeic acid with Langmuirian binding constants estimated as 106 mol-1 dm3. The molecular structure of the pyrene-appended boronic acid affects the ability to bind caffeic acid as well as, more importantly, the fluxional transformation of the strongly bound (high oxidation potential) into the weakly bound (low oxidation potential) form. The resulting design principles for improved boronic acid receptors are discussed.
Original languageEnglish
Pages (from-to)1883-1888
Number of pages6
JournalNew Journal of Chemistry
Volume37
Issue number7
Early online date13 Mar 2013
DOIs
Publication statusPublished - Jul 2013

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