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
07 صفر 1443
Accepted
21 ربيع الأول 1443
First published
22 ربيع الأول 1443

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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