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

Research output: Contribution to journalArticle

18 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)1811-1816
Number of pages6
JournalChemistry - An Asian Journal
Volume7
Issue number8
DOIs
StatePublished - Aug 1 2012

Fingerprint

Porphyrins
Tapes
Electrons
Oxidation
Chemical stability
Photons
Solubility
Organic solvents
Absorption spectra
Condensation
Acids
scandium triflate
dichlorodicyanobenzoquinone
dipyrromethane

Keywords

  • conjugation
  • cyclic voltammetry
  • dimer
  • electron-deficient compounds
  • porphyrinoids

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

Cite this

Mori, H., Tanaka, T., Aratani, N., Lee, B. S., Kim, P., Kim, D., & Osuka, A. (2012). An electron-deficient porphyrin tape. Chemistry - An Asian Journal, 7(8), 1811-1816. https://doi.org/10.1002/asia.201200247
Mori, Hirotaka ; Tanaka, Takayuki ; Aratani, Naoki ; Lee, Byung Sun ; Kim, Pyosang ; Kim, Dongho ; Osuka, Atsuhiro. / An electron-deficient porphyrin tape. In: Chemistry - An Asian Journal. 2012 ; Vol. 7, No. 8. pp. 1811-1816.
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Mori, H, Tanaka, T, Aratani, N, Lee, BS, Kim, P, Kim, D & Osuka, A 2012, 'An electron-deficient porphyrin tape', Chemistry - An Asian Journal, vol. 7, no. 8, pp. 1811-1816. https://doi.org/10.1002/asia.201200247

An electron-deficient porphyrin tape. / Mori, Hirotaka; Tanaka, Takayuki; Aratani, Naoki; Lee, Byung Sun; Kim, Pyosang; Kim, Dongho; Osuka, Atsuhiro.

In: Chemistry - An Asian Journal, Vol. 7, No. 8, 01.08.2012, p. 1811-1816.

Research output: Contribution to journalArticle

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AU - Mori, Hirotaka

AU - Tanaka, Takayuki

AU - Aratani, Naoki

AU - Lee, Byung Sun

AU - Kim, Pyosang

AU - Kim, Dongho

AU - Osuka, Atsuhiro

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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.

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Mori H, Tanaka T, Aratani N, Lee BS, Kim P, Kim D et al. An electron-deficient porphyrin tape. Chemistry - An Asian Journal. 2012 Aug 1;7(8):1811-1816. https://doi.org/10.1002/asia.201200247