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Charge Transfer Properties of Benzo[b]thiophene Ferrocenyl Complexes

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journal contribution
posted on 28.09.2015, 00:00 by Alessandro Donoli, Annalisa Bisello, Roberta Cardena, Marco Crisma, Laura Orian, Saverio Santi
The synthesis of 2-ferrocenylbenzo­[b]­thiophene, 3-ferrocenylbenzo­[b]­thiophene, 1,1′-bis­(2-indene)­ferrocene, and the two isomers of 1,1′-bis­(2-benzo­[b]­thiophene)­ferrocene was efficiently achieved by using the palladium-catalyzed Negishi C,C cross-coupling reaction of the appropriate bromobenzo­[b]­thiophene derivative with ferrocenylzinc chloride. The accessibility of differently substituted benzo­[b]­thiophenes and a comparison with indene analogues allowed an in-depth investigation on how the geometric modifications and the presence of sulfur affect their physical properties. The molecular structure of 3-ferrocenylbenzo­[b]­thiophene has been determined by X-ray diffraction. Electrochemistry and UV–vis–NIR spectroscopy, in particular the appearance upon oxidation of a charge transfer absorption in the NIR region, are rationalized through quantum chemistry calculations and in the framework of the Hush theory.