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The synthesis of bisisoindigo, a near IR absorbing electron acceptor in which two isoindigo units are ring-fused along the 6 and 7 positions, is reported. An electron-deficient bisisatin was first synthesized using the Martinet isatin synthesis, after which two concurrent aldol condensations with 1-alkyl-2-oxindole yielded the ring-fused isoindigo dimer. The ring fusion significantly extends the conjugation length of the molecule relative to the isoindigo parent compound. The bisisoindigo sub-unit was then coupled to 2,2′-bithiophene, yielding a new organic semiconductor with a donor–acceptor structure. Both bisisoindigo and the donor–acceptor compound absorb light well into the near IR; the donor–acceptor compound features an absorption edge of almost 1000 nm in the solid state. Both compounds were employed in prototype organic photovoltaic devices alongside common electron donors and acceptors.

Bisisoindigo: using a ring-fusion approach to extend the conjugation length of isoindigo