Synthesis of a linear bis-porphyrin with a Ru(phen)(2)(2+)-complexed 2,2 '-bipyridine spacer

Bruce, James I.; Chambron, Jean-Claude; Kolle, Phillipe and Sauvage, Jean-Pierre (2002). Synthesis of a linear bis-porphyrin with a Ru(phen)(2)(2+)-complexed 2,2 '-bipyridine spacer. Journal of the Chemical Society: Perkin Transactions 1, Perkin Tra(10) pp. 1226–1231.

DOI: https://doi.org/10.1039/b202407c

Abstract

A linear bis-porphyrin bridged by a 5,5-diphenyl-2,2-bipyridine rod-like spacer complexing a [Ru(phen)2]2+ fragment has been synthesized in 7.4% yield by one-pot condensation of 3,5-di-tert-butylbenzaldehyde, 4,4-dimethyl-3,3-dihexyl-2,2-methylenedipyrrole and the [Ru(phen)2]2+ complex of 5,5-bis(p-formylphenyl)-2,2-bipyridine, followed by chloranil oxidation. The protected dialdehyde (5,5-bis[(5,5-dimethyl-1,3-dioxan-2-yl)phenyl]-2,2-bipyridine) was obtained in 80% yield by Suzuki coupling of 2-[4-(5,5-dimethyl-1,3-dioxan-2-yl)phenyl]-4,4,5,5-tetramethyl-1,3-dioxaborolane and 5,5-dibromo-2,2-bipyridine, using [Pd(PPh3)4] as catalyst. A new procedure is reported for the preparation of 5,5-dibromo-2,2-bipyridine, which is obtained in 80% yield by Stille homocoupling of 2,5-dibromopyridine in the presence of hexamethylditin.

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