Synthesis and through-space charge transfer of dioctyloxy diperfluorohexyl substituted [2.2]paracyclophane-1,9-diene

Abstract

Paracyclophanedienes containing dioctyloxy and diperfluorohexyl substituents have been synthesized in three steps from substituted dithia[3.3]paracyclophanes and the structures were fully characterized by nuclear magnetic resonance spectroscopy. A mixture of pseudo-geminal and pseudo-ortho diastereomers is produced and the pure compounds can be simply obtained by flash column chromatography using hexane as an eluent. The pseudo-geminal isomer exhibited more efficient through space charge transfer between electron donating and withdrawing substituents than the pseudo-ortho isomer. The absorption and photoluminescence spectra of both pseudo-geminal and pseudo-ortho diastereomers in a more polar solvent show the solvatochromism of the through-space electron transfer between dioctyloxy substituted phenyl and diperfluorohexyl substituted phenyl rings.