Trimeric and Tetrameric Electron-Deficient Porphyrin Tapes

Hirotaka Mori, Taeyeon Kim, Dongho Kim, Atsuhiro Osuka

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

New hybrid porphyrin tapes comprising meso-3,5-di-tert-butylphenyl- substituted ZnII-porphyrins (D) and mesopentafluorophenyl-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 Dn porphyrin tapes, and all display remarkably coplanar structures favorable for p-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 p-conjugation path is extended from 12 to ADDA and the molecular polarizability of ADA is larger than that of AAA.
Original languageEnglish
Pages (from-to)1454-1463
Number of pages10
JournalChemistry - An Asian Journal
Volume11
Issue number9
DOIs
Publication statusPublished - 2016 May 23

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