Dibenzophosphapentaphenes: exploiting P chemistry for gap fine-tuning and coordination-driven assembly of planar polycyclic aromatic hydrocarbons

Pierre-Antoine Bouit; Aude Escande; Rózsa Szűcs; Dénes Szieberth; Christophe Lescop; László Nyulászi; Muriel Hissler; Régis Réau

doi:10.1021/ja300171y

Dibenzophosphapentaphenes: exploiting P chemistry for gap fine-tuning and coordination-driven assembly of planar polycyclic aromatic hydrocarbons

J Am Chem Soc. 2012 Apr 18;134(15):6524-7. doi: 10.1021/ja300171y. Epub 2012 Apr 9.

Authors

Pierre-Antoine Bouit¹, Aude Escande, Rózsa Szűcs, Dénes Szieberth, Christophe Lescop, László Nyulászi, Muriel Hissler, Régis Réau

Affiliation

¹ Institut des Sciences Chimiques de Rennes, UMR 6226 CNRS - Université de Rennes 1, Campus de Beaulieu, 35042 Rennes Cedex, France.

PMID: 22475075
DOI: 10.1021/ja300171y

Abstract

A synthetic route to planar P-modified polycylic aromatic hydrocarbons (PAHs) is described. The presence of a reactive σ(3),λ(3)-P moiety within the sp(2)-carbon scaffold allows the preparation of a new family of PAHs displaying tunable optical and redox properties. Their frontier molecular orbitals (MOs) are derived from the corresponding phosphole MOs and show extended conjugation with the entire π framework. The coordination ability of the P center allows the coordination-driven assembly of two molecular PAHs onto a Au(I) ion.