Twisted, two-faced porphyrins as hosts for bispyridyl fullerenes: Construction and photophysical properties

Yongshu Xie, Jonathan P. Hill, Amy Lea Schumacher, Atula S.D. Sandanayaka, Yasuyuki Araki, Paul A. Karr, Jan Labuta, Francis D'Souza, Osamu Ito, Christopher E. Anson, Annie K. Powell, Katsuhiko Ariga

Research output: Contribution to journalArticlepeer-review

43 Citations (Scopus)


A new class of multichromophoric host compounds capable of binding guest species through two-point coordinative interaction is reported. The hosts contain appended zinc porphyrin (ZnP) moieties connected covalently by acetylene linkages to a central oxoporphyrinogen (OxP) unit through its central macrocyclic nitrogen atoms. Orientation of the ZnP groups was controlled to some extent by variation of the substitution pattern at the OxP N-substituent. Up to four porphyrin appendages are accommodated, and two cofacial bis-porphyrin interaction sites can be created in orthogonal geometry within the same molecule. The multiporphyrin hosts, termed "twisted, two-faced porphyrins", abbreviated as OxP-(MPx)n where M = 2H or Zn, n = 2 or 4, and x = meta (m) or para (p), and their complexes with a bis-4-pyridyl-substituted fullerene derivative were investigated using spectroscopic, electrochemical, and photochemical methods. Porphyrin fluorescence emission of the OxP-(ZnPx)n compounds is quenched substantially compared to that of pristine ZnP with this quenching being more significant for OxP-(ZnPx)2 than for the OxP-(ZnPx)4. The electrochemically determined highest occupied molecular orbital to lowest unoccupied molecular orbital (HOMO-LUMO) gap for the OxP-(ZnPx)n series is ∼1.65 eV. For the OxP-(ZnPx)n series, charge separation from the singlet excited ZnP to OxP occurs, while, for their complexes with the bis-pyridyl fullerene derivative, charge separation appears to occur predominantly from the singlet excited porphyrin to fullerene.

Original languageEnglish
Pages (from-to)10559-10572
Number of pages14
JournalJournal of Physical Chemistry C
Issue number28
Publication statusPublished - 2008 Jul 17

ASJC Scopus subject areas

  • Electronic, Optical and Magnetic Materials
  • Energy(all)
  • Physical and Theoretical Chemistry
  • Surfaces, Coatings and Films


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