Advances in Biofuels and Renewable Feedstocks Technologies in Eastern Kentucky: Study 1: (Armstrong and Preston) Furan Derivatives: Utilization of Biomass Byproducts as Renewable Building Blocks

With the increasing demand of petroleum continuing to negatively influence the United States economy and security, transitioning to renewable fuels and high value chemicals has become a high priority in the sciences. While Biofuels have been given a large amount of attention, replacement of petroleum-based resins, polymers, and feedstocks is just as critical. Recent advances in carbohydrate research have shown that furans represent a truly renewable building block for novel conducting polymers. These so-called “biopolymers” have the potential to be incorporated into next generation electronics (e.g., field-effect transistors (FETs), organic light-emitting diodes (OLEDs), and organic photovoltaic (OPV) cells) all at a fraction of the price of traditional inorganic materials. Our focus has been to develop novel organic and organometallic compounds from furans derived from carbohydrates. Thus, this project focuses on the downstream development of high value chemicals in the Biorefinery sector. Specially, by starting with a common saccharification co-product, furfural, we have been able to form a 5,6-fused ring pyridazine, 1,2- C5H3(CC4H3ONH)(CC4H3ON), in modest yield (41%) from a 1,2-difuroyl cyclopentadiene (fulvene), 1,2-C5H3(COC4H3O)(COHC4H3O). In addition, several manganese and ruthenium tricarbonyl complexes have been formed utilizing this furoyl fulvene. This was accomplished by transmetallating with its thallium salt and Mn(CO)5Br or Re(CO)5Br and was done so in good yields (61 and 66%). Subsequent ring closure with hydrazine hydrate afforded their pyridazyl complexes (76%). This poster will discuss the application of organic conducting materials in electronics, the role of furans in alternative energy applications, and the synthesis and characterization of various fused-ring furan derivatives