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).

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