Presentation description

The purpose of this project was to investigate the chemistry of fluorinated molecules in three different projects. These projects were Ligand Design for Oxidative Addition of Platinum, Fluorinated Host Guest Networks, and Synthesis of Perfluorobenzene. Ligand design for oxidative addition involved synthesizing various ligands based on a previously used azobenzene ligand. Due to a difficulty in extraction many of the ligands could not be isolated for reaction with the platinum compound, to fix this more work is needed in a careful extraction. Fluorinated Host Guest Networks involved the creation of sulfonate and guanidinium hydrogen bonded crystal structures with organic side chains creating spacers that could trap other molecules which could then be viewed in the crystal structure. This part of the project wanted to create fluorinated organic side chains as this is an area not previously explored in work on these host guest networks. It was found that a sulfonic acid when mixed with guanidine carbonate readily produced large crystals whose structure could be measured with X-ray Crystallography. The particularly novel challenge in this area was producing fluorinated analogues to previously tried organic side chains particularly a pentafluoro-benzenesulfonic acid and heptafluoronaphthalenesulfonic acid. The benzenesulfonic acid was readily synthesized and a crystal was easily grown, however the naphthalene is still in the process of being synthesized. Lastly the project Synthesis of Perfluorobenzene compared several methods of synthesis for decafluoroazobenzene. The general synthesis of Azobenzenes involved an oxidation of aniline; traditional methods use lead acetate, however this is a very toxic reagent so it should be avoided. The first method tested followed this use of lead acetate but instead used the much less toxic potassium ferricyanide with KOH as a reducing agent. The second method tested was the use of mechanochemistry to oxidize the aniline using bleaching powder in a ball mill. Lastly a method involving a phase transfer reaction was tested.