Abstract

Cyclic voltamograms of the solvatochromic dye 5-nitro-5′-dimethylamino-2,2′-bisthiophene (1), introduced recently as a sensitive π* probe, were recorded in different solvents. An EPR spectrum of the anionic radical of 1 in DMSO was obtained and compared with other spectra of analogous substituted bisthiophene radicals. It was found that the presence of a donor– acceptor pair of substituents in 1−⋅ reduces significantly the rotational barrier of the radical compared with the unsubstituted bithienyl radical anion 2−⋅. This is the result of an electronic repulsion between the donor ring fragment and the added electron in the coplanar radical, which does not exist in 2−⋅. © 1998 John Wiley & Sons, Ltd.

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