Extended triphenylamine conjugated systems derivatized by perfluorophenyl groups

Two triphenylamine derivatives bearing terminal perfluorophenyl groups have been synthesized. Their HOMO, LUMO levels and electronic band gap have been evaluated by spectroscopic and electrochemical measurements and rationalized with theoretical calculations. X-ray structure analysis of crystals allowed the observation of multiple intermolecular interactions due to the presence of the perfluorophenyl pendant groups. The multiplication of these interactions explains the differences between calculated (in gas phase) and observed (in solid states) structures.

Graphical abstractTriphenylamine derivatives bearing terminal perfluorophenyl groups have been synthesized and exhibit, in the solid state, multiple phenyl-perfluorophenyl and perfluorophenyl–perfluorophenyl interactions.Figure optionsDownload full-size imageDownload as PowerPoint slide