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

Journal of the American Chemical Society
Jung-Ho HongDong-Gyu Cho

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.

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Citations

Sep 23, 2016·Chemical Reviews·Timothy D Lash
Nov 4, 2017·Angewandte Chemie·Adil S AslamDong-Gyu Cho
May 10, 2018·Chemistry : a European Journal·Jung-Ho HongDong-Gyu Cho
Mar 10, 2020·Chemistry : a European Journal·Hidemitsu UnoMasayoshi Takase
Feb 13, 2021·Organic Letters·Jung-Ho HongDong-Gyu Cho
Jan 20, 2021·Angewandte Chemie·Bartosz SzyszkoLechosław Latos-Grażyński
Apr 21, 2021·The Journal of Organic Chemistry·Avisikta Sinha, Mangalampalli Ravikanth
Aug 3, 2021·Physical Chemistry Chemical Physics : PCCP·Markus RauhalahtiMikael P Johansson
Aug 20, 2019·Organic Letters·Bartosz SzyszkoLechosław Latos-Grażyński
Oct 3, 2017·Journal of the American Chemical Society·Xian-Sheng KeJonathan L Sessler
Mar 22, 2019·Journal of the American Chemical Society·Bartosz SzyszkoLechosław Latos-Grażyński
Nov 20, 2018·Journal of the American Chemical Society·Xian-Sheng KeJonathan L Sessler
May 23, 2018·Journal of the American Chemical Society·Xian-Sheng KeJonathan L Sessler
Feb 8, 2022·Organic Letters·Avisikta Sinha, Mangalampalli Ravikanth

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