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 journalArticle

56 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

Fingerprint

Triazoles
Porphyrins
porphyrins
assemblies
Azides
Cycloaddition
Cycloaddition Reaction
cycloaddition
Hydrogen Bonding
Dimers
nitrogen atoms
Protons
Zinc
Hydrogen bonds
solid solutions
Nitrogen
assembly
zinc
dimers
Oxygen

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Dimeric assemblies from 1,2,3-triazole-appended Zn(II) porphyrins with control of NH-tautomerism in 1,2,3-triazole. / Maeda, Chihiro; Yamaguchi, Shigeru; Lkeda, Chusaku; Shinokubo, Hiroshi; Osuka, Atsuhiro.

In: Organic Letters, Vol. 10, No. 4, 21.02.2008, p. 549-552.

Research output: Contribution to journalArticle

Maeda, Chihiro ; Yamaguchi, Shigeru ; Lkeda, Chusaku ; Shinokubo, Hiroshi ; Osuka, Atsuhiro. / Dimeric assemblies from 1,2,3-triazole-appended Zn(II) porphyrins with control of NH-tautomerism in 1,2,3-triazole. In: Organic Letters. 2008 ; Vol. 10, No. 4. pp. 549-552.
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AU - Shinokubo, Hiroshi

AU - Osuka, Atsuhiro

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