Redox-Active Heteroacene Chromophores Derived from a Non-Linear Aromatic Diimide

07 June 2019, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


This work describes a three-step chromatography-free protocol for the synthesis of a novel organic materials
building block, dichlorinated mellophanic diimide (MDI), that is shown to undergo nucleophilic substitution
with a variety of ortho disubstituted benzenes to yield a series of chromophores. Furthermore, 1,2,4,5-
tetrasubstituted benzenes can be used to synthesize tetraimide heteropentacene derivatives endcapped by
MDI motifs. The fine-tuning effects of heteroatom identity were investigated by UV-Vis and fluorescence
spectroscopy, cyclic and differential pulse voltammetries, and density functional theory calculations. Oxidation
of diamino MDI derivatives yields di- and tetraimide functionalized azaacenes with significantly lowered LUMO
levels (down to –4.49 eV), narrowed bandgaps (down to 1.81 eV), and high molar absorptivities (up to 84,000
M–1 cm–1).


aromatic diimides
mellophanic diimide


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