Heterocycles and their derivatives have long been of interest for use in advanced electronic applications. Due to their unique properties including environmental stability, high processibility, and low production cost, organic-based electronic materials are an attractive alternative to conventional inorganic semiconductors. The growing interest and demand for renewable energy and next generation electronic devices has led to the incorporation of aromatic heterocycles into field-effect transistors (FETs), organic light-emitting diodes (OLEDs), and organic photovoltaic (OPV) cells. Specially, thiophenes, furans, and pyridazines (6 membered aromatic rings containing two adjacent nitrogen atoms) represent alluring building blocks for electronic materials due to their ease of synthesis and stability. Polymers and discrete molecules/oligomers incorporating these heterocycles have shown promise in a number of commercial and industrial applications. Our current investigation focuses on the off-metal and transition metal chemistry of thiophenes, furans, and pyridazines, namely, the formation of fused-ring complexes bound η5 (eta-5) to a metal through a Cp moiety. By including a transition metal into fused-heterocycles, we hope to create hybrid materials which blend the synthetic versatility of organics with the novel structural and electronic properties that inorganic moieties possess. For example, formation of the desired complexes, [M(CO)3{η5-1,2-C5H3(1,4-(R)2N2C2}] (M = Mn, Re), was accomplished from a 1,2-diketo precursor, [M{h5-1,2-C5H3(COR)2}(CO)3] (R= 4-ClPh, 4-MeOPh, 5-BrTp). Reaction of these 1,2-diketo complexes with excess hydrazine under mild conditions (room temperature) afforded the desired pyridazine complexes in good yield (60-83%). These complexes display high solid state stability in air and relatively good stability in non-halogenated solvents.

Synthetic heterocycles and their applications in energy and advanced electronics

251st National Meeting (2016)

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