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

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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    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