Trimeric and Tetrameric Electron-Deficient Porphyrin Tapes

Hirotaka Mori; Taeyeon Kim; Dongho Kim; Atsuhiro Osuka

doi:10.1002/asia.201600241

Trimeric and Tetrameric Electron-Deficient Porphyrin Tapes

Hirotaka Mori, Taeyeon Kim, Dongho Kim, Atsuhiro Osuka

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

8 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 language	English
Pages (from-to)	1454-1463
Number of pages	10
Journal	Chemistry - An Asian Journal
Volume	11
Issue number	9
DOIs	https://doi.org/10.1002/asia.201600241
Publication status	Published - 2016 May 23

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title = "Trimeric and Tetrameric Electron-Deficient Porphyrin Tapes",

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.",

author = "Hirotaka Mori and Taeyeon Kim and Dongho Kim and Atsuhiro Osuka",

year = "2016",

month = may,

day = "23",

doi = "10.1002/asia.201600241",

language = "English",

volume = "11",

pages = "1454--1463",

journal = "Chemistry - An Asian Journal",

issn = "1861-4728",

publisher = "John Wiley and Sons Ltd",

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TY - JOUR

T1 - Trimeric and Tetrameric Electron-Deficient Porphyrin Tapes

AU - Mori, Hirotaka

AU - Kim, Taeyeon

AU - Kim, Dongho

AU - Osuka, Atsuhiro

PY - 2016/5/23

Y1 - 2016/5/23

N2 - 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.

AB - 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.

U2 - 10.1002/asia.201600241

DO - 10.1002/asia.201600241

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SN - 1861-4728

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SP - 1454

EP - 1463

JO - Chemistry - An Asian Journal

JF - Chemistry - An Asian Journal

IS - 9

ER -

Trimeric and Tetrameric Electron-Deficient Porphyrin Tapes

Abstract

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