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Issue 4, 2012
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Solution and surface-confined chloride anion templated redox-active ferrocene catenanes

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Abstract

The first examples of ferrocene containing catenanes, in solution and assembled on a surface are described. Chloride anion templation is exploited to synthesize redox-active [2]- and [3]-catenanes via Grubbs' ring closing metathesis, utilizing a novel ferrocene-appended isophthalamide macrocycle. X-ray crystal structures of both catenanes were determined. The ability of the [2]catenane to selectively bind and characteristically sense its chloride anion template is demonstrated by use of 1H NMR and electrochemical voltammetric techniques. Self-assembled monolayers of analogous surface-confined catenanes have been prepared on gold. In addition to being characterized by cyclic voltammetry and ellipsometry, detailed information regarding the structure of the catenane monolayers has been provided by use of angle integrated high resolution X-ray photoelectron spectroscopy.

Graphical abstract: Solution and surface-confined chloride anion templated redox-active ferrocene catenanes

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Publication details

The article was received on 11 Nov 2011, accepted on 09 Dec 2011 and first published on 06 Jan 2012


Article type: Edge Article
DOI: 10.1039/C2SC00909A
Citation: Chem. Sci., 2012,3, 1080-1089
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    Solution and surface-confined chloride anion templated redox-active ferrocene catenanes

    N. H. Evans, H. Rahman, A. V. Leontiev, N. D. Greenham, G. A. Orlowski, Q. Zeng, R. M. J. Jacobs, C. J. Serpell, N. L. Kilah, J. J. Davis and P. D. Beer, Chem. Sci., 2012, 3, 1080
    DOI: 10.1039/C2SC00909A

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