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Issue 29, 2012
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The synthesis and characterisation of novel ferrocenyl polyphenylenes

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Abstract

This work describes the synthesis and characterisation of a new series of polyphenylenes with up to four ferrocenyl moieties. The synthetic route involves the preparation of a number of novel precursors. Cyclopentadienones, generated from the two-fold Knoevenagel condensation of di-ferrocenyl propanones and diketones, are used in [2 + 4] Diels–Alder cycloadditions with appropriately substituted acetylenes. 13 is amongst the compounds isolated. It is the largest ferrocenyl-supported polyaromatic hydrocarbon (PAH) to date. Prepared via a Sonogashira cross-coupling reaction between ethynyl-Fc and iodo-HBC, it comprises a hexa-peri-hexabenzocoronene (HBC) core linked via acetylene to a ferrocenyl unit (Fc). The electrochemical and absorption properties of the ferrocenyl-polyphenylenes and the fully conjugated 13 are discussed. The NLO data for 13, determined by hyper Rayleigh scattering techniques, are compared to those of similar fulleryl-based compounds in the literature.

Graphical abstract: The synthesis and characterisation of novel ferrocenyl polyphenylenes

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Publication details

The article was received on 06 Mar 2012, accepted on 20 May 2012 and first published on 21 May 2012


Article type: Paper
DOI: 10.1039/C2DT30542A
Citation: Dalton Trans., 2012,41, 8850-8860
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    The synthesis and characterisation of novel ferrocenyl polyphenylenes

    D. J. Roberts, D. Nolan, G. M. Ó Máille, G. W. Watson, A. Singh, I. Ledoux-Rak and S. M. Draper, Dalton Trans., 2012, 41, 8850
    DOI: 10.1039/C2DT30542A

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