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Discrete Conjugated Porphyrin Tapes with an Exceptionally Small Bandgap
Author(s) -
Tsuda A.,
Osuka A.
Publication year - 2002
Publication title -
advanced materials
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 10.707
H-Index - 527
eISSN - 1521-4095
pISSN - 0935-9648
DOI - 10.1002/1521-4095(20020104)14:1<75::aid-adma75>3.0.co;2-8
Subject(s) - porphyrin , conjugated system , homo/lumo , materials science , band gap , crystal (programming language) , photochemistry , benzoquinone , molecular orbital , infrared , optoelectronics , molecule , optics , polymer , organic chemistry , physics , chemistry , composite material , computer science , programming language
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 III (OTf) 3 directly produces fully π‐conjugated fused porphyrin 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.