Four-substrate guided inquiry scheme towards the synthesis of 2,2’-bipyridine adducts
American Chemical Society National Meeting in Philadelphia, PA
American Chemical Society National Meeting
Philadelphia, PA, USA
The project focuses on the preparation of 2,2’-bipyridine adducts for future use as ligands in novel organometallic ruthenium complexes. The first specific aim of the project includes utilizing substituted versus un-substituted bromo pyridines to explore the effects of electron donating groups on the efficiency of the reactions. The second specific aim of the project focuses on evaluating the differences of palladium(0) versus palladium(II) catalysts on the reactions.
Specifically, the compounds being synthesized are unsubstituted 2,2’-bipyridine versus a 4,4’-dimethylated, a 5,5’-dimethylated, or a 4,4’-diamino 2,2’-bipyridine. The synthetic method being explored is a homo-coupling reaction relying on a palladium catalyst. The catalyst being used is either tetrakis(triphenylphosphine)palladium(0) or a bis(triphenylphosphine)palladium(II) chloride in xylene as the choice.
The methodology has been developed to ensure an air-free environment, by assembling the closed reaction chamber in a nitrogen glovebox. The reaction is completed on a Schlenk-line assembly under an inert argon atmosphere, evaluated under different time frames varying from 12 to 72 hours. Reaction progress is monitored with thin layer chromatography. The product is isolated and purified via acidic extraction, and if needed, sublimation. Compound characterization is carried out utilizing NMR and FT-IR. The bipyridine building blocks, based on their excellent bidentate ligands with complexing abilities, will be incorporated into ruthenium complexes in a collaborative project, increasing the photosensitivity of these complexes, and opening the doors for many applications ranging from synthetic photovoltaics to anti-cancer activity.
Wilkinson, Kylie; Gruzmark, Fiona; and Aukszi, Beatrix, "Four-substrate guided inquiry scheme towards the synthesis of 2,2’-bipyridine adducts" (2020). Chemistry and Physics Faculty Proceedings, Presentations, Speeches, Lectures. 346.