Synthesis, Redox Properties, and Electronic Spectra of Sterically Crowded Triarylphosphines Conjugated with Electron Acceptors

Abstract

Synthesis, redox properties, and electronic spectra of the sterically crowded triarylphosphines conjugated with π-electron systems, especially electron acceptors such as carbonyl group, are briefly reviewed. The sterically crowded triarylphosphines conjugated with various π-electron systems were synthesized from the common synthetic intermediate, (bromoaryl)phosphine, by conventional manner. The sterically crowded triarylphosphines conjugated with the electron acceptors exhibit visible absorption and fluorescence with large Stokes shift. Large solvent effect, redshift in polar solvent, and good correlation with the difference of the oxidation potential of the phosphine moiety and the reduction potential of the acceptor moiety suggest polar excited state resulting from HOMO-LUMO transition.

GRAPHICAL ABSTRACT

Keywords:

• Triarylphosphine
• π-electron systems
• redox potential
• electronic spectrum

Acknowledgments

We thank Grants-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology, Japan (Nos. 22605001, 17310063, 15550025) for financial support, Research and Analytical Center for Giant Molecules, Graduate School of Science, Tohoku University, for taking mass spectra and elemental analysis.