Synthesis of Photochromic Phosphines by Pd-Catalyzed Annulation Reaction of Alkynes Bearing Phosphinyl Substituent with a Silacyclopropene

Abstract

The synthesis of phosphines with light controlled basicity is presented in this study. A methodological approach for the preparation of these unconventional photochromic phosphines based on a dithienylethene organic moiety is reported. It relies on the palladium-catalyzed annulation of alkynyl phosphines in the presence of a 2,3-Dithienylsilacyclopropene. Accordingly, a diphenyphosphino moiety is connected to the organic photochrome thanks to different linkers. Their influence on the photochromism and on the phosphinyl group basicity is studied and evaluated based on experimental an NMR descriptor as well as DFT calculations.

Keywords: annulation reaction; dithienylethenes; phosphines; photochromism; siloles.