An Ethyne‐Bridged Porphyrin‐Hexaphyrin‐Porphyrin Triad That Undergoes a Thermal Transannular Cyclization

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  • Kazuma Honjo
    Department of Chemistry, Graduate School of Science Kyoto University Sakyo-ku Kyoto 606-8502 Japan
  • Hirotaka Mori
    Department of Chemistry, Graduate School of Science Kyoto University Sakyo-ku Kyoto 606-8502 Japan
  • Atsuhiro Osuka
    Department of Chemistry, Graduate School of Science Kyoto University Sakyo-ku Kyoto 606-8502 Japan

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<jats:title>Abstract</jats:title><jats:p>An ethyne‐bridged Ni<jats:sup>2+</jats:sup> porphyrin‐[26]hexaphyrin‐Ni<jats:sup>2+</jats:sup> porphyrin triad (<jats:bold>4</jats:bold>) has been prepared and shown to adopt a dumbbell‐like conformation despite the two bulky porphyrinylethynyl groups at the hinge positions of the hexaphyrin. The <jats:sup>1</jats:sup>H NMR and UV/vis/NIR spectra of <jats:bold>4</jats:bold> revealed that the aromatic nature of the [26]hexaphyrin unit was significantly mitigated via conjugative interaction with the porphyrinylethynyl substituents. Thermal transannular cyclization of <jats:bold>4</jats:bold> proceeded smoothly to give vinylene‐bridged triad <jats:bold>12</jats:bold>, in which the π‐systems of the Ni<jats:sup>2+</jats:sup> porphyrins and [26]hexaphyrin are not conjugated and the aromatic character of the latter is enhanced.</jats:p>

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