TY - JOUR
T1 - 2-(Naphthalen-1-yl)thiophene as a New Motif for Porphyrinoids
T2 - Meso-Fused Carbaporphyrin
AU - Hong, Jung Ho
AU - Aslam, Adil S.
AU - Ishida, Masatoshi
AU - Mori, Shigeki
AU - Furuta, Hiroyuki
AU - Cho, Dong Gyu
N1 - Funding Information:
This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF), funded by the Ministry of Education, Science, and Technology (Grant No. NRF-2013R1A1A2057508) and JSPS Grant-in-Aid for Scientific Research (25248039 and 26810024). D.-G.C. thanks the JSPS Invitational Fellowship (ID No. S151715).
Publisher Copyright:
© 2016 American Chemical Society.
PY - 2016/5/4
Y1 - 2016/5/4
N2 - 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.
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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U2 - 10.1021/jacs.6b01063
DO - 10.1021/jacs.6b01063
M3 - Article
AN - SCOPUS:84966340144
SN - 0002-7863
VL - 138
SP - 4992
EP - 4995
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 15
ER -