2-(Naphthalen-1-yl)thiophene as a New Motif for Porphyrinoids: Meso-Fused Carbaporphyrin

Jung Ho Hong, Adil S. Aslam, Masatoshi Ishida, Shigeki Mori, Hiroyuki Furuta, Dong Gyu Cho

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

The first synthesis of meso-fused carbaporphyrin via a premodification method was accomplished by substituting two pyrrole moieties and one meso-carbon with 2-(naphthalen-1-yl)thiophene. The obtained global π-conjugation pathway of the macrocycle noticeably disturbs the 10π local aromaticity of naphthalene, and its aromatic nature was supported by NMR spectroscopy together with nucleus-independent chemical shift, anisotropy of the induced current density, and harmonic oscillator stabilization energy calculations. In addition, the meso-fused carbaporphyrin also allowed the formation of a square planar PdII complex.

Original languageEnglish
Pages (from-to)4992-4995
Number of pages4
JournalJournal of the American Chemical Society
Volume138
Issue number15
DOIs
Publication statusPublished - May 4 2016

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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