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ABSTRACT: This article reports the preparation of a range of phenyl, pyridyl and pyrazinyl substituted pyridazines via the inverse electron demand [2 + 4] Diels-Alder reaction between 3,6-di(2-pyridyl)-1,2,4,5-tetrazines (bptz) and 3,6-di(2-pyrazinyl)-1,2,4,5-tetrazines (bpztz) and suitable dienophiles including acenaphthalene. The resulting polyaromatic compounds vary systematically in the number of aromatic substituents and the number and position of N-heteroatoms. For four of these compounds, the effect of the molecular changes on the solid-state structures were investigated using single crystal X-ray crystallography. The pyridazines were used as bidentate ligands in {M(II)(bipy)(2)} and tris(homoleptic) complexes (M = Fe, Ru). The optical and electrochemical properties of these complexes reflect the electron accepting character of the new ligands. The facial and meridional isomers of the tris complexes could be separated by column chromatography (on silica), thus allowing a spectral comparison of their absorption and emission properties. The solid-state structures of several of the metal complexes are discussed, including that of the facial isomer of the tris Ru(II) complex of 3,6-bis(2-pyridyl)-4,5-bis(4-pyridyl)pyridazine--a potential preformed geometric motif for the predirected construction of supramolecular assemblies.
Dalton Transactions 08/2011; 40(32):8206-12. · 3.84 Impact Factor
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Dalton Transactions 02/2011; 40:8206-8212. · 3.84 Impact Factor
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CrystEngComm 01/2009; 11:1505-1508. · 3.84 Impact Factor
