Study on Aromatic Phosphines for Novel Fluorometry of Hydroperoxides (I) -Synthesis and Spectral Properties of Diphenyl Aryl Phosphines and Their Oxides

Abstract

1-Naphthyldiphenylphosphine (NDPP), 9-anthryldiphenylphosphine (ADPP) and diphenyl-1-pyrenylphosphine (DPPP) and their oxides were prepared from triphenyl-phosphine (TPP) and the corresponding aryl bromides. These phosphines had no fluorescence, but their oxides showed blue fluorescence. The order of fluorescence intensities of these oxides were DPPP oxide > ADPP oxide > NDPP oxide. Hydroperoxides oxidized these phosphines to the corresponding oxides quantitatively. The relative reactivities were TPP > NDPP > DPPP > ADPP. The phosphines were stable in the dark, however, unstable in the light in chloroform. The reaction is proposed as novel type of fluorometry for hydroperoxides.