An electron-deficient porphyrin tape

Hirotaka Mori; Takayuki Tanaka; Naoki Aratani; Byung Sun Lee; Pyosang Kim; Dongho Kim; Atsuhiro Osuka

doi:10.1002/asia.201200247

An electron-deficient porphyrin tape

Hirotaka Mori, Takayuki Tanaka, Naoki Aratani, Byung Sun Lee, Pyosang Kim, Dongho Kim^*, Atsuhiro Osuka

^*Corresponding author for this work

Chemistry

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

20 Scopus citations

Abstract

Hexakis(pentafluorophenyl)-substituted meso-meso-linked Zn ^II-diporphyrin (9), which was prepared by the acid-catalyzed cross-condensation of 1,1,2,2-tetrapyrroethane (5) with dipyrromethane dicarbinol (6), was converted into meso-meso,β-β,β-β triply linked Zn ^II-diporphyrin 3 by oxidation with 2,3-dichloro-5,6- dicyanobenzoquinone (DDQ) and Sc(OTf) ₃. Beside the red-shifted absorption spectrum and split first oxidation potential that are common to the triply-linked Zn ^II-diporphyrins, diporphyrin 3 exhibited considerably improved chemical stability owing to a lowered HOMO and good solubility in common organic solvents. The two-photon absorption (TPA) cross-section and S ₁-state lifetime of compound 3 were 1700 GM and 3.3 ps, respectively.

Original language	English (US)
Pages (from-to)	1811-1816
Number of pages	6
Journal	Chemistry - An Asian Journal
Volume	7
Issue number	8
DOIs	https://doi.org/10.1002/asia.201200247
State	Published - Aug 2012

Keywords

conjugation
cyclic voltammetry
dimer
electron-deficient compounds
porphyrinoids

ASJC Scopus subject areas

Biochemistry
Organic Chemistry

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title = "An electron-deficient porphyrin tape",

abstract = "Hexakis(pentafluorophenyl)-substituted meso-meso-linked Zn II-diporphyrin (9), which was prepared by the acid-catalyzed cross-condensation of 1,1,2,2-tetrapyrroethane (5) with dipyrromethane dicarbinol (6), was converted into meso-meso,β-β,β-β triply linked Zn II-diporphyrin 3 by oxidation with 2,3-dichloro-5,6- dicyanobenzoquinone (DDQ) and Sc(OTf) 3. Beside the red-shifted absorption spectrum and split first oxidation potential that are common to the triply-linked Zn II-diporphyrins, diporphyrin 3 exhibited considerably improved chemical stability owing to a lowered HOMO and good solubility in common organic solvents. The two-photon absorption (TPA) cross-section and S 1-state lifetime of compound 3 were 1700 GM and 3.3 ps, respectively.",

keywords = "conjugation, cyclic voltammetry, dimer, electron-deficient compounds, porphyrinoids",

author = "Hirotaka Mori and Takayuki Tanaka and Naoki Aratani and Lee, {Byung Sun} and Pyosang Kim and Dongho Kim and Atsuhiro Osuka",

year = "2012",

month = aug,

doi = "10.1002/asia.201200247",

language = "English (US)",

volume = "7",

pages = "1811--1816",

journal = "Chemistry - An Asian Journal",

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T1 - An electron-deficient porphyrin tape

AU - Mori, Hirotaka

AU - Tanaka, Takayuki

AU - Aratani, Naoki

AU - Lee, Byung Sun

AU - Kim, Pyosang

AU - Kim, Dongho

AU - Osuka, Atsuhiro

PY - 2012/8

Y1 - 2012/8

N2 - Hexakis(pentafluorophenyl)-substituted meso-meso-linked Zn II-diporphyrin (9), which was prepared by the acid-catalyzed cross-condensation of 1,1,2,2-tetrapyrroethane (5) with dipyrromethane dicarbinol (6), was converted into meso-meso,β-β,β-β triply linked Zn II-diporphyrin 3 by oxidation with 2,3-dichloro-5,6- dicyanobenzoquinone (DDQ) and Sc(OTf) 3. Beside the red-shifted absorption spectrum and split first oxidation potential that are common to the triply-linked Zn II-diporphyrins, diporphyrin 3 exhibited considerably improved chemical stability owing to a lowered HOMO and good solubility in common organic solvents. The two-photon absorption (TPA) cross-section and S 1-state lifetime of compound 3 were 1700 GM and 3.3 ps, respectively.

AB - Hexakis(pentafluorophenyl)-substituted meso-meso-linked Zn II-diporphyrin (9), which was prepared by the acid-catalyzed cross-condensation of 1,1,2,2-tetrapyrroethane (5) with dipyrromethane dicarbinol (6), was converted into meso-meso,β-β,β-β triply linked Zn II-diporphyrin 3 by oxidation with 2,3-dichloro-5,6- dicyanobenzoquinone (DDQ) and Sc(OTf) 3. Beside the red-shifted absorption spectrum and split first oxidation potential that are common to the triply-linked Zn II-diporphyrins, diporphyrin 3 exhibited considerably improved chemical stability owing to a lowered HOMO and good solubility in common organic solvents. The two-photon absorption (TPA) cross-section and S 1-state lifetime of compound 3 were 1700 GM and 3.3 ps, respectively.

KW - conjugation

KW - cyclic voltammetry

KW - dimer

KW - electron-deficient compounds

KW - porphyrinoids

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DO - 10.1002/asia.201200247

M3 - Article

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EP - 1816

JO - Chemistry - An Asian Journal

JF - Chemistry - An Asian Journal

IS - 8

ER -

An electron-deficient porphyrin tape

Abstract

Keywords

ASJC Scopus subject areas

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