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Issue 7, 2016
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Regioselective phenylene-fusion reactions of Ni(ii)-porphyrins controlled by an electron-withdrawing meso-substituent

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Abstract

Oxidation of 10,15,20-triaryl Ni(II)-porphyrins bearing an electron-withdrawing substituent at the 5-position with DDQ and FeCl3 gave 10,12- and 18,20-doubly phenylene-fused Ni(II)-porphyrins regioselectively. A doubly phenylene-fused meso-chloro porphyrin thus prepared was reductively coupled to give a mesomeso linked dimer, which was further converted to a quadruply phenylene-fused mesomeso, β–β, β–β triply linked Zn(II)–diporphyrin via inner-metal exchange followed by oxidation with DDQ and Sc(OTf)3. As compared to the usual mesomeso, β–β, β–β triply linked Zn(II)-diporphyrin, this π-extended porphyrin dyad exhibits a smaller HOMO–LUMO gap and a larger two-photon absorption cross-section.

Graphical abstract: Regioselective phenylene-fusion reactions of Ni(ii)-porphyrins controlled by an electron-withdrawing meso-substituent

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Supplementary files

Article information


Submitted
09 Dec 2015
Accepted
01 Mar 2016
First published
01 Mar 2016

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2016,7, 4059-4066
Article type
Edge Article
Author version available

Regioselective phenylene-fusion reactions of Ni(II)-porphyrins controlled by an electron-withdrawing meso-substituent

N. Fukui, S. Lee, K. Kato, D. Shimizu, T. Tanaka, S. Lee, H. Yorimitsu, D. Kim and A. Osuka, Chem. Sci., 2016, 7, 4059
DOI: 10.1039/C5SC04748J

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