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Determination of the surface acidity of a free-base corrole in a self-assembled monolayer

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Abstract

Mixed self-assembled monolayers (SAMs) containing a corrole moiety have been prepared to examine their electrochemical properties and surface acidity, with the eventual goal of biosensor development. Mixed SAMs consisting of 6-mercapto-hexanol (6-MHO) and 8-amino-1-octanethiol (8-AOT) in varying ratios were modified with a free-base corrole and characterized via Osteryoung square-wave voltammetry and contact angle measurements. The surface acidity of the free-base corrole was determined using an electrochemical titration method, with pK a values established at 6.4 when using Fe(CN) 4−6 /Fe(CN) 3−6 as a redox probe and at 6.7 when using iodide, and assigned to the CorH4 + ⇌ CorH3 + H+ equilibrium.

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Acknowledgments

The authors gratefully acknowledge European Union Marie Curie Transfer of Knowledge Research Grants MTKD-CT-2006-042708, the Polish Ministry of Sciences and Higher Education no. 105/6.PR UE/2007/7, and statutory funds of the Institute of Animal Reproduction and Food Research of the Polish Academy of Sciences, Olsztyn, Poland. The authors also thank the IWT (Institute for the Promotion of Innovation through Science and Technology in Flanders) for a doctoral fellowship to Thien H. Ngo and the KU Leuven for continuing financial support.

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Authors and Affiliations

  1. Department of Biosensors, Institute of Animal Reproduction and Food Research, Polish Academy of Sciences, Tuwima 10, 10-747, Olsztyn, Poland

    Wienand Nulens, Iwona Grabowska, Hanna Radecka & Jerzy Radecki

  2. Molecular Design and Synthesis, Department of Chemistry, Katholieke Universiteit Leuven, Celestijnenlaan 200F, 3001, Leuven, Belgium

    Thien Huynh Ngo, Wouter Maes & Wim Dehaen

  3. Institute for Materials Research (IMO), Research Group Organic and (Bio)polymeric Chemistry, Hasselt University, Universitaire Campus, Agoralaan Building D, 3590, Diepenbeek, Belgium

    Wouter Maes

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  1. Wienand Nulens
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  2. Iwona Grabowska
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Correspondence to Jerzy Radecki.

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Nulens, W., Grabowska, I., Ngo, T.H. et al. Determination of the surface acidity of a free-base corrole in a self-assembled monolayer. J Incl Phenom Macrocycl Chem 71, 499–505 (2011). https://doi.org/10.1007/s10847-010-9889-y

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  • DOI: https://doi.org/10.1007/s10847-010-9889-y

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