The synthesis and characterisation of novel ferrocenyl polyphenylenes.
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.
School of Chemistry, University of Dublin, Trinity College, College Green, Dublin 2, Ireland.
Dilwyn J
DJ
Roberts
Deanne
D
Nolan
Gearóid M Ó
GM
Máille
Graeme W
GW
Watson
Anu
A
Singh
Isabelle
I
Ledoux-Rak
Sylvia M
SM
Draper