Synthesis, structures, and optical and electrochemical properties of benzoporphycenes

Daiki Kuzuhara, John Mack, Hiroko Yamada, Tetsuo Okujima, Noboru Ono, Nagao Kobayashi

Research output: Contribution to journalArticlepeer-review

58 Citations (Scopus)

Abstract

The first facile syntheses of free-base di- and tetrabenzoporphycenes and their metal complexes are reported, based on retro-Diels-Alder reactions of the corresponding bicyclo[2.2.2]octadiene-fused porphycenes, prepared by McMurray coupling of α,α'-diformyldipyrrole. The photophysical and electrochemical properties are analyzed based on UV/Vis absorption, magnetic circular dichroism (MCD), and fluorescence emission, lifetime and quantum yield measurements, cyclic and differential pulse voltammetry (CV and DPV) and time-dependent DFT calculations based on B3LYP geometry optimizations. Benzoporphycenes are found to be prime candidates for future use in photodynamic therapy.

Original languageEnglish
Pages (from-to)10060-10069
Number of pages10
JournalChemistry - A European Journal
Volume15
Issue number39
DOIs
Publication statusPublished - 2009 Oct 5

Keywords

  • Benzoporphycenes
  • Density functional calculations
  • Fluorescence
  • Magnetic circular dichroism
  • Porphyrinoids

ASJC Scopus subject areas

  • Chemistry(all)

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