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- Title
Trimeric and Tetrameric Electron-Deficient Porphyrin Tapes.
- Authors
Mori, Hirotaka; Kim, Taeyeon; Kim, Dongho; Osuka, Atsuhiro
- Abstract
New hybrid porphyrin tapes comprising meso-3,5-di- tert-butylphenyl-substituted ZnII-porphyrins ( D) and meso-pentafluorophenyl-substituted ZnII-porphyrins ( A) were synthesized via cross-condensation of meso-formyl porphyrins 1, 5, and 9 with oligopyrromethanes 2 and 6 as key steps. These hybrid tapes exhibit improved solubilities and enhanced chemical stability as compared with original D n porphyrin tapes, and all display remarkably coplanar structures favorable for π-conjugation. The absorption spectrum of ADDA displays Q-like bands at 1400 and 1657 nm with a vibronic structure characteristic of porphyrinoids. The cyclic voltammograms exhibited positively shifted oxidation and reduction waves in the order of DDD< DAD< ADA< AAA. Tetrameric tape ADDA displays five reversible waves in a narrow range of 1.13 V. Two-photon absorption (TPA) measurement confirmed that the π-conjugation path is extended from 12 to ADDA and the molecular polarizability of ADA is larger than that of AAA.
- Subjects
TRIMERIZATION; ELECTRONS; PORPHYRINS; LIGHT absorption; POLARIZABILITY (Electricity)
- Publication
Chemistry - An Asian Journal, 2016, Vol 11, Issue 9, p1454
- ISSN
1861-4728
- Publication type
Article
- DOI
10.1002/asia.201600241