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Synfacts 2007(3): 0270-0270  
DOI: 10.1055/s-2007-968205
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Bromination of Electron-Deficient Aromatic Molecules

Contributor(s): Timothy M. Swager, Trisha L. Andrew
F. Chaignon, M. Falkenström, S. Karlsson, E. Blart, F. Odobel*, L. Hammarström*
Université de Nantes, France and Uppsala University, Sweden
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Publication History

Publication Date:
20 February 2007 (online)

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Significance

The ruthenium dyad 3 was synthesized in 8.5% overall yield using standard metal-catalyzed cross-coupling techniques; as opposed to the conventional analogue in which the Ru(bpy)3 moieties are connected through the imide nitrogen, the two Ru(bpy)3 arms of 3 are linked through its naphthalene core. The rate of photo­induced intramolecular electron transfer from ruthenium to the naphthalenebisimide (NBI) core of 3 was found to be 1000-fold faster than that for the conventional analogue due to the increased electronic coupling afforded by the naphthyl bridge.