Octupolar trisporphyrin conjugates exhibiting strong two-photon absorption

Ju Won Seo, So Young Jang, Dongho Kim, Hee Joon Kim

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

We report octupolar trisporphyrin conjugates, derived from the symmetrical functionalization of a triphenylamine core with three ethynylporphyrin wings, exhibiting largely enhanced two-photon absorption (TPA) compared to the porphyrin monomers. Octupolar trisporphyrin conjugate tris-H2P was synthesized by the Pd(0)-catalyzed Sonogashira cross-coupling reaction of tris(4-iodophenyl)amine with 5,10,15-tri-(p-tolyl)-20-ethynylporphyrin, and fully characterized by various spectroscopic methods and elemental analysis. The optimized geometry of tris-H2P obtained by semi-empirical AM1 calculations reveals that tris-H2P adopts a propeller-shaped structure. Our photophysical studies strongly manifest that the trisporphyrin conjugates are promising octupolar fluorophores with effective π-conjugation over the porphyrin wings through the octupolar core. The trisporphyrin conjugates exhibit much larger TPA cross-section values in comparison with the monomers; the TPA cross-section σ(2) value of tris-ZnP (11,800 GM) exceeds that of mono-ZnP (630 GM) by about 20 times.

Original languageEnglish
Pages (from-to)2733-2739
Number of pages7
JournalTetrahedron
Volume64
Issue number12
DOIs
Publication statusPublished - 2008 Mar 17

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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