Halide anion mediated dimerization of a meso-unsubstituted N-confused porphyrin

Hiroyuki Furuta, Hideki Nanami, Tatsuki Morimoto, Takuji Ogawa, Vladimir Král, Jonathan L. Sessler, Vincent Lynch

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

The new N-confused porphyrin (NCP) derivatives, meso-unsubstituted β-alkyl-3-oxo N-confused porphyrin (3-oxo-NCP) and related macrocycles, were synthesized from appropriate pyrrolic precursors by a [3+1]-type condensation reaction. 3-Oxo-NCP forms a self-assembled dimer in dichloromethane that is stabilized by complementary hydrogen-bonding interactions arising from the peripheral amide-like moieties. The protonated form of 3-oxo-NCP was observed to bind halide anions (F - , Cl - ) through the outer NH and the inner pyrrolic NH groups, thus affording a dimer in dichloromethane. The structure of the chloride-bridged dimer in the solid state was determined by X-ray diffraction analysis.

Original languageEnglish
Pages (from-to)592-599
Number of pages8
JournalChemistry - An Asian Journal
Volume3
Issue number3
DOIs
Publication statusPublished - Mar 7 2008

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Dimerization
Porphyrins
Anions
Dimers
Methylene Chloride
Condensation reactions
Hydrogen Bonding
Amides
X-Ray Diffraction
X ray diffraction analysis
Chlorides
Hydrogen bonds
Derivatives

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Organic Chemistry

Cite this

Furuta, H., Nanami, H., Morimoto, T., Ogawa, T., Král, V., Sessler, J. L., & Lynch, V. (2008). Halide anion mediated dimerization of a meso-unsubstituted N-confused porphyrin. Chemistry - An Asian Journal, 3(3), 592-599. https://doi.org/10.1002/asia.200700130

Halide anion mediated dimerization of a meso-unsubstituted N-confused porphyrin. / Furuta, Hiroyuki; Nanami, Hideki; Morimoto, Tatsuki; Ogawa, Takuji; Král, Vladimir; Sessler, Jonathan L.; Lynch, Vincent.

In: Chemistry - An Asian Journal, Vol. 3, No. 3, 07.03.2008, p. 592-599.

Research output: Contribution to journalArticle

Furuta, H, Nanami, H, Morimoto, T, Ogawa, T, Král, V, Sessler, JL & Lynch, V 2008, 'Halide anion mediated dimerization of a meso-unsubstituted N-confused porphyrin', Chemistry - An Asian Journal, vol. 3, no. 3, pp. 592-599. https://doi.org/10.1002/asia.200700130
Furuta, Hiroyuki ; Nanami, Hideki ; Morimoto, Tatsuki ; Ogawa, Takuji ; Král, Vladimir ; Sessler, Jonathan L. ; Lynch, Vincent. / Halide anion mediated dimerization of a meso-unsubstituted N-confused porphyrin. In: Chemistry - An Asian Journal. 2008 ; Vol. 3, No. 3. pp. 592-599.
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AU - Král, Vladimir

AU - Sessler, Jonathan L.

AU - Lynch, Vincent

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