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 alternative 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.  One such class of heterocycles, pyridazines (6 membered aromatic rings containing two adjacent nitrogen atoms) represents an alluring building block for electronic materials due to their ease of synthesis and stability.  However, very little is known about the materials properties of pyridazines or the feasibility of incorporating pyridazines into electronic devices. Our current investigation focuses on the transition metal chemistry of pyridazines, namely, the formation of a fused-ring pyridazine complex bound ?5 (eta-5) to a metal through a Cp moiety.  By including a transition metal into the pyridazine, we hope to create hybrid materials which blend the synthetic versatility of organics with the novel structural and electronic properties that inorganic moieties possess.    Formation of the desired complexes, [M(CO)3{?5-1,2-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.  This poster will discuss the synthesis and characterization of various pyridazine complexes and their potential role in advanced materials applications.

Synthesis, structure, and characterization of some group VII pyridazyl complexes for advanced electronic applications

246th National Meeting (2013)

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