Perfluorooctylation of aromatic compounds with perfluoroazooctane upon 185 nm irradiation in a two-phase system

Abstract

An efficient method for the preparation of perfluorooctylated aromatic and heteroaromatic compounds has been developed using photolysis of perfluoroazooctane (E)-1 upon 185 nm irradiation. The use of a two-phase system made up of a perfluorohexane solution of (E)-1 and a suitable aromatic compound has proved efficient for this reaction. The photolytic mechanism of (E)-1 upon 185 nm irradiation has also been investigated on the basis of quantum yield, light intensity dependence and UV–VIS spectra. It is shown that (E)-1 is photoisomerized by one photon absorption to the (Z)-isomer, with subsequent extrusion of nitrogen by a second photon absorption.