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

doi:10.1021/jacs.6b01063

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 journal › Article › peer-review

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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 Pd^II complex.

Original language	English
Pages (from-to)	4992-4995
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	138
Issue number	15
DOIs	https://doi.org/10.1021/jacs.6b01063
State	Published - 4 May 2016

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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.",

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AU - Mori, Shigeki

AU - Furuta, Hiroyuki

AU - Cho, Dong Gyu

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AB - 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.

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

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