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MDI_MainText 6June2019.pdf (1.13 MB)

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

submitted on 06.06.2019, 15:30 and posted on 07.06.2019, 15:03 by Stella Luo, Kellie Stellmach, Stella Ikuzwe, Dennis Cao
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).


American Chemical Society Petroleum Research Fund (57163-UNI1)

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Email Address of Submitting Author


Macalester College


United States

ORCID For Submitting Author


Declaration of Conflict of Interest

No conflict of interest

Version Notes

version submitted for peer review