Synthesis and characterization of terthiophene bearing stable radicals

The synthesis and characterization of a new terthiophene bearing stable radical II is described. Through a cross coupling reaction between 2-tributylstannylthiophene and 6-(2,5-dibromo-thiophene-3-yl)pyridine-2-carboxaldehyde (2), 6-[2,2′:5′,2″]terthiophen-3′-ylpyridine-2-carboxaldehyde (3) was prepared. The condensation of 3 with 2, 4-diisopropylcarbonohydrazide bis-hydrochloride affords the heterocyclic tetrazane (4), which was oxidized with 1,4-benzoquinone to form the stable radical II. II characterized by IR, ESR, and cyclic voltammetry. Oxidative electropolymerization of II and its precursor 4 at oxidation peak potential of the terthiophene using cyclic voltammetric scans produces radical functionalized polyterthiophene on a platinum electrode (poly(II)-Pt). (author)