Issue 45, 2021

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 SN2 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.

Graphical abstract: Sidechain engineering of N-annulated perylene diimide molecules

Supplementary files

Article information

Article type
Communication
Submitted
14 sept. 2021
Accepted
27 oct. 2021
First published
28 oct. 2021

New J. Chem., 2021,45, 21001-21005

Sidechain engineering of N-annulated perylene diimide molecules

M. Martell, M. U. Ocheje, B. S. Gelfand, S. Rondeau-Gagné and G. C. Welch, New J. Chem., 2021, 45, 21001 DOI: 10.1039/D1NJ04423K

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