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.

Figure optionsDownload as PowerPoint slide