Conjugated Thiophene-Fused Isatin Dyes through Intramolecular Direct Arylation

We report on the design, synthesis, and properties of innovative, planar, pi-conjugated compounds in which a thiophene ring is fused with the skeleton of the naturally occurring dye isatin. The synthesis is achieved in high yields making use of an intramolecular direct arylation reaction as the key step, making the overall process potentially scalable. The synthetic sequence has been demonstrated also for an isatin bearing fluorine substituents on the aromatic ring. NMR and X-ray studies demonstrate the crosstalk occurring between the fused, coplanar, and conjugated moieties, making these novel dyes with a donor acceptor character. Cyclic voltammetry and UV-vis studies confirm very interesting HOMO LUMO-levels and energy gaps for the new compounds.