Dimeric assemblies from 1,2,3-triazole-appended Zn(II) porphyrins with control of NH-tautomerism in 1,2,3-triazole

Chihiro Maeda, Shigeru Yamaguchi, Chusaku Lkeda, Hiroshi Shinokubo, Atsuhiro Osuka

Research output: Contribution to journalArticlepeer-review

58 Citations (Scopus)

Abstract

Cu(l)-catalyzed 1,3-dipolar cycloaddition of meso-ethynyl Zn(II) porphyrin with benzyl azide efficiently provides meso-1-benzyl-1H-1,2,3-triazolyl Zn(II) porphyrin, which assembles to form a slipped cofacial dimer by the complementary coordination of the triazole nitrogen atom at the 3-position to the zinc center of a second porphyrin moiety both in the solid and solution states. Removal of the benzyl protection and introduction of a 2-ethoxycarbonylphenyl moiety greatly stabilize the dimeric assembly through an additional hydrogen bonding interaction between the NH proton of 2H-1,2,3-triazole and the carbonyl oxygen.

Original languageEnglish
Pages (from-to)549-552
Number of pages4
JournalOrganic Letters
Volume10
Issue number4
DOIs
Publication statusPublished - Feb 21 2008
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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