We are interested in potential applications of metallocene-fused tropones and derivatives as organic electronic materials. Condensation of 1,2-diformylferrocene with acetone or 1,3-diphenylacetone in the presence of KOH leads to the ferrocene-fused tropone (?5-2,4-cyclopentadien-1-yl)[(1,2,3,3a,8a-?)-1,6-dihydro-6-oxo-1-azulenyl]iron and its 5,7-diphenyl derivative  , E = O, as previously reported by Tirouflet. In the presence of piperidine, 1,2-diformylferrocene and 1,3-diphenylacetone gives the Michael addition of piperidine to the tropone. Lawesson's reagent converts the ferrocene-fused tropones to thiotropones (1 , E = S) or detached azulenethiols (2 , E = S). Reactions of the ferrocene-fused thiotropones with hydroxylamine give the corresponding oximes (1 , E = NOH). Products are characterized by using spectroscopic methods and X-ray crystallography. Their electronic properties are studied by using cyclic voltammetry and UV-visible spectroscopy.

Synthesis and characterization of ferrocene-fused tropones, thiotropones and tropone oximes

247th National Meeting (2014)

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