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

12 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

Fingerprint

Thiophenes
Pyrroles
Anisotropy
Induced currents
Chemical shift
Thiophene
Naphthalene
Nuclear magnetic resonance spectroscopy
Current density
Magnetic Resonance Spectroscopy
Carbon
Stabilization
naphthalene

All Science Journal Classification (ASJC) codes

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

Cite this

2-(Naphthalen-1-yl)thiophene as a New Motif for Porphyrinoids : Meso-Fused Carbaporphyrin. / Hong, Jung Ho; Aslam, Adil S.; Ishida, Masatoshi; Mori, Shigeki; Furuta, Hiroyuki; Cho, Dong Gyu.

In: Journal of the American Chemical Society, Vol. 138, No. 15, 04.05.2016, p. 4992-4995.

Research output: Contribution to journalArticle

Hong, Jung Ho ; Aslam, Adil S. ; Ishida, Masatoshi ; Mori, Shigeki ; Furuta, Hiroyuki ; Cho, Dong Gyu. / 2-(Naphthalen-1-yl)thiophene as a New Motif for Porphyrinoids : Meso-Fused Carbaporphyrin. In: Journal of the American Chemical Society. 2016 ; Vol. 138, No. 15. pp. 4992-4995.
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