A study of diphenylpyrenylphosphine : a fluorescent molecule with many uses : an honors thesis (HONRS 499)

Abstract

Diphenylpyrenylphosphine (DPPP) is a molecule that with a myriad of potential uses. Current published research on the molecule extols it uses in the food industry as a highly sensitive toxicity indicator. The research presented shows a preliminary framework for the characterization of DPPP and its oxide (DPPP=O). Thus far, no suitable crystals have been isolated to present the X-ray analysis of the molecules; therefore, no accurate data on cone angle and spatial arrangement of the molecule can be reported. DPPP=O recrystallization should be obtained in the near future by using a large non-polar organic solvent, such as mesitylene, in dilute conditions. DPPP has a chemical shift at -13.34 ppm in the 31P NMR spectrum, while its oxide has a shift at 33.39 ppm. Nickel carbonyl experiments using infrared spectroscopy yield a successive decrease in the v(CO)A1 stretching frequency as the number of pyrenyl groups substituted on triphenylphosphine increases from 0 - 2. The respective frequencies observed are: 2069.35 cm -1, 2068.96 cm-1, and 2068.45 cm-1. This data indicates increasing donor ability of the phosphorus lone pair as the number of pyrenyl groups increases.