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

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 nap...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2016-04, Vol.138 (15), p.4992-4995
Main Authors: Hong, Jung-Ho, Aslam, Adil S, Ishida, Masatoshi, Mori, Shigeki, Furuta, Hiroyuki, Cho, Dong-Gyu
Format: Article
Language:English
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Summary: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.6b01063