Synthesis of an H-aggregated thiophene–phthalimide based small molecule via microwave assisted direct arylation coupling reactions

•Design of an electron deficient π-conjugated small molecule.•Optimized synthesis using microwave assisted direct arylation reactivity.•Observed large blue shift in maximum absorption upon solution to film transition.•Single crystal XRD reveal strong face-to-face stacking.•Rare example of a symmetrical small molecule exhibiting H-aggregation.

We report on the design, optimized synthesis, and characterization of a thiophene–phthalimide based small molecule. We show that microwave irradiation is a useful technique to accelerate direct arylation cross-coupling reactions, and that the thiophene–phthalimide architecture can lead to face-to-face intermolecular π-stacking, resulting in pronounced blue shifts in the absorption maximum upon a solution to condensed state transition.

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