Pictet–Spengler Synthesis of Quinoline-Fused Porphyrins and Phenanthroline-Fused Diporphyrins

Ke Gao, Norihito Fukui, Seok I. Jung, Hideki Yorimitsu, Dongho Kim, Atsuhiro Osuka

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

Doubly and quadruply quinoline-fused porphyrins were effectively synthesized through a reaction sequence consisting of Suzuki–Miyaura coupling of β-borylated porphyrins with 2-iodoaniline and subsequent Pictet–Spengler cyclization. These quinoline-fused porphyrins display red-shifted absorption bands and higher electron-accepting abilities. This synthetic protocol also allowed the synthesis of phenanthroline-fused porphyrin dimers, which bound either a NiIIor ZnIIcation. The resultant metal complexes displayed further red shifted absorption spectra and molecular twists to effect an almost perpendicular arrangement of the two porphyrins.

Original languageEnglish
Pages (from-to)13038-13042
Number of pages5
JournalAngewandte Chemie - International Edition
Volume55
Issue number42
DOIs
Publication statusPublished - 2016 Oct 10

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Phenanthrolines
Porphyrins
Absorption spectra
Cyclization
Coordination Complexes
Metal complexes
Dimers
quinoline
Electrons

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Cite this

Gao, Ke ; Fukui, Norihito ; Jung, Seok I. ; Yorimitsu, Hideki ; Kim, Dongho ; Osuka, Atsuhiro. / Pictet–Spengler Synthesis of Quinoline-Fused Porphyrins and Phenanthroline-Fused Diporphyrins. In: Angewandte Chemie - International Edition. 2016 ; Vol. 55, No. 42. pp. 13038-13042.
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Pictet–Spengler Synthesis of Quinoline-Fused Porphyrins and Phenanthroline-Fused Diporphyrins. / Gao, Ke; Fukui, Norihito; Jung, Seok I.; Yorimitsu, Hideki; Kim, Dongho; Osuka, Atsuhiro.

In: Angewandte Chemie - International Edition, Vol. 55, No. 42, 10.10.2016, p. 13038-13042.

Research output: Contribution to journalArticle

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