Eastern Kentucky University
Organometallic Pyridazine Complexes for Electronic Materials Applications
Institution
Eastern Kentucky University
Faculty Advisor/ Mentor
Nathan Tice
Abstract
Due to their unique properties including environmental stability, high processibility, and low production cost, organic-based electronic materials that contain heterocycles are an attractive alternative to conventional inorganic semiconductors. 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 η5 (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. We have found that due to the relative instability of the free pyridazines, the formation of the more stabile cymantrene complexes [Mn(CO)3{η5-1,2-C5H3(1,4-(R)2N2C2}], is best accomplished from a 1,2-diketo precursor, [Mn{η5-1,2-C5H3(COR)2}(CO)3] (R= 4-ClPh, 4-MeOPh, 5-BrTp). Reaction of these 1,2-diketo cymantrenes with excess hydrazine under mild conditions (room temperature) afforded the desired pyridazine complexes in good yield (65-83%). These complexes display high solid state stability in air and relatively good stability in solution. The analogous ring-closure transformation was also observed on Re(CO)3 substrates, with the formation of [Re(CO)3{η5-1,2-C5H3(1,4-(5-ClC4H2S))2N2C2}] in moderate yield (52%). This poster will discuss the synthesis and characterization of various pyridazine complexes and their potential role in next generation electronic materials.
Organometallic Pyridazine Complexes for Electronic Materials Applications
Due to their unique properties including environmental stability, high processibility, and low production cost, organic-based electronic materials that contain heterocycles are an attractive alternative to conventional inorganic semiconductors. 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 η5 (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. We have found that due to the relative instability of the free pyridazines, the formation of the more stabile cymantrene complexes [Mn(CO)3{η5-1,2-C5H3(1,4-(R)2N2C2}], is best accomplished from a 1,2-diketo precursor, [Mn{η5-1,2-C5H3(COR)2}(CO)3] (R= 4-ClPh, 4-MeOPh, 5-BrTp). Reaction of these 1,2-diketo cymantrenes with excess hydrazine under mild conditions (room temperature) afforded the desired pyridazine complexes in good yield (65-83%). These complexes display high solid state stability in air and relatively good stability in solution. The analogous ring-closure transformation was also observed on Re(CO)3 substrates, with the formation of [Re(CO)3{η5-1,2-C5H3(1,4-(5-ClC4H2S))2N2C2}] in moderate yield (52%). This poster will discuss the synthesis and characterization of various pyridazine complexes and their potential role in next generation electronic materials.