AN IMPROVED SYNTHETIC METHOD FOR DIPHENYL-1-PYRENYLPHOSPHINE AND THE PROPERTIES AND STRUCTURE OF ITS BORANE ADDUCT

Abstract

An efficient synthetic method for diphenyl-1-pyrenylphosphine, DPPP, has been developed involving a low temperature Li-Br exchange reaction using the commercially available 1-bromopyrene. An estimate of the donor ability of this phosphine has been obtained by measuring the A₁υ (CO) band of the Ni(CO)₃L complex which was found to be 0.4 wave numbers lower than that from the PPh₃ complex indicating that DPPP is a slightly better donor than PPh₃. The BH₃ adduct of DPPP has been prepared and, as the situation for the oxide of DPPP, this adduct is fluorescent. It is estimated that the fluorescence intensity is about half that of DPPPO. An x-ray structure of this adduct has been obtained, and the bond lengths and angles appear to be in expected ranges.

Keywords:

• Borane
• diphenyl-1-pyrenylphosphine
• DPPP
• structure

Thanks is given to the donors of the Petroleum Research Fund, administered by the American Chemical Society, along with the Ball State University Faculty Grants Program and Honors College for support of this research. Funding for the fluorescence system came from a Howard Hughes Medical Institute grant.

Notes

∗The method described in Akasaka et al. ⁹ involves reacting PPh₂ ⁻ with 1-bromopyrene providing a 13.6% yield. There is also mention of grignard-based reaction in reference 8.