Sidechain engineering of N-annulated perylene diimide molecules

Abstract

The synthesis and characterization of six new N-annulated perylene diimide (N-PDI) molecules consisting of different alkyl-based heteroatom and waxy infused sidechains is reported. Amino, urea, quaternary methyl ammonium, iminopyridine, hexadecyl and pyridine moieties were all appended to the pyrrolic N-position of N-annulated PDI. These N-PDI derivatives have been synthesized using facile S_N2 chemistry resulting in high yields and without the need for purification via column chromatography. To further demonstrate the functional diversification offered by N-PDI we appended a cyano group to the 6,7-bay positions opposite the N-annulation site and tested utility in organic field effect transistor devices. Complete characterization of these N-PDI derivatives was completed using UV-Vis spectroscopy, cyclic voltammetry and solubility determination to observe how the appended sidechains affect structure–properties relationships.