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Discrete Conjugated Porphyrin Tapes with an Exceptionally Small Bandgap

An Ag I -promoted meso-meso coupling reaction has been extended to prepare discrete 100 nm long linear arrays of porphyrins. Oxidation of the resulting phenyl end-capped meso-meso linked porphyrins using a combination of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and Sc I I I (OTf) 3 directly produces fully π-conjugated fused porphysin arrays (porphyrin tapes) of 10 nm molecular size. This research news article presents their synthesis. X-ray crystal structures, and optical and electronic properties. Among these, the extremely small highest occupied molecular orbital-lowest unoccupied molecular orbital (HOMO-LUMO) optical gaps that reach into the infrared region suggest many applications of these compounds in materials science.