Publication Date

12-2012

Advisor(s) - Committee Chair

Dr. Chad Snyder (Director), Dr. Bangbo Yan, Dr. Cathleen Webb

Degree Program

Department of Chemistry

Degree Type

Master of Science

Abstract

Heterocyclic organic and organometallic compounds (i.e. polypyrrole), and their derivatives, have been of great interest for conductive polymers due to their novel properties and environmental stability as compared to their non-aromatic analogs (i.e. polyacetylene). Our current interest focus upon the potential role of metal ligand bound pyridazines as the next generation of electronic devices that utilize the metal ligands bound to organics as the semiconducting material. Pyridazine is a 6-membered aromatic ring with two adjacent nitrogen atoms. These are promising candidates for a variety of materials and commercial applications; but they are difficult to get a metal ligand to fuse to the aromatic ring.

Our recent efforts focused in attaching Rhenium and Manganese ligands/substituents (process in which is called doping) that would cause oxidation to occur to our polymer making it a p-type polymer. Since p-type polymers charge carriers leave a vacancy that does not delocalize completely. This vacancy (known as a hole) or a radical cation that only partially delocalizes over several monomeric units causing them to be structurally deformed. This deformed structure is at a higher energy than that of an undoped polymer. Typical carriers in organic semiconductors are holes and electrons in a π-orbital. So when these molecules of π-conjugated systems have a π-bond overlap (or π- stacking), electrons can move via these π-electron clouds overlapping thus causing an electrical current.

Our worked focused on the synthesis of pyridazines and their organometallic rhenium complexes and polymer research. Several aryl-substituted 5,6-fused pyridazines have been synthesized but none have been documented until this study. The main goal of the research was to fully characterize the general synthesis of furan containing organometallic complexes, [M(CO)3{η5-1,2-C5H3(CC4H3ON)(CC4H3ON)}] (M = Re or Mn) (4B). We successfully characterized the ability to attach a metal organic ligand to pyridazine though IR and NMR. However, when attempts were made to recrystallize our product, we yielded an orange-brown, block like crystal of 1,2- C5H3(CC4H3ONH)(CC4H3ON) (5) in which our metal ligand group fell off and we were left with pyridazine and inorganics. Though, we successfully got an X-ray characterization and electronic studies of compound 5 which are reported herein.

Disciplines

Chemistry | Organic Chemistry

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