O‐doped zig‐zag molecular ribbons

A. Berenzin, N. Biot, T. Battisti, D. Bonifazi
Angew. Chem., Int. Ed. 2018, 57 (29), 8942-8946.
DOI: 10.1002/anie.201803282


The synthesis of the first O‐doped molecular rhombic ribbon featuring two zig‐zag peripheries, has been achieved. This includes oxidative C‐C and C‐O bond formations that allowed the stepwise elongation and planarization of a hexaoxa‐congener of 2,7‐periacenoacene. X‐ray diffraction analysis corroborated the flat structure and the topology of the zig‐zag O‐doped edges. Photophysical and electrochemical investigations showed that the extension of the PXX into the molecular ribbon induces a noticeable shrinking of the molecular band gap devised by a dramatic rising of the HOMO energy level, a desirable property for p‐type organic semiconductors.

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