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Synthesis and Characterization of a New Family of Spin Bearing TTF Ligands

Synthesis and Characterization of a New Family of Spin Bearing TTF Ligands

M'hamed Chahma, Xiaoshu Wang, Art van der Est, Melanie Pilkington

J Org Chem. 2006 Mar 31;71(7):2750-5.

PMID: 16555829

Abstract:

The syntheses and characterization of two new tetrathiafulvalene (TTF) derivatives bearing pyridine-based substituents and 1,5'-dimethyl-6-oxoverdazyl radicals are described. The TTF-pyridine and bipyridine aldehydes were prepared via a palladium-catalyzed cross-coupling reaction between mono(tributylstannyl)tetrathiafulvalene (3) and the appropriate formylpyridyl halides (4). The radical precursors, the corresponding 1,2,4,5-tetrazanes, were prepared by condensation of the bis(1-methylhydrazide) of carbonic acid with the TTF bearing pyridyl aldehyde. Oxidation of tetrazanes 8 and 9 with 1,4-benzoquinone afforded the donor radicals 1 and 2 as 1:1 complexes with hydroquinone. Both complexes are stable in the solid state and their electronic properties have been characterized by EPR, cyclic voltammetry, and UV/vis spectroscopy. The TTF core of both compounds was oxidized both chemically and electrochemically to afford the corresponding cation diradical species. The electronic properties of both donor radicals have been probed by cyclic voltammetry, UV-vis spectroscopy, and preliminary EPR measurements.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP59020109	3-(Tributylstannyl)pyridine		59020-10-9	Price

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