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Title: Regioselective phenylene-fusion reactions of Ni(II)-porphyrins controlled by an electron-withdrawing: Meso -substituent
Authors: Fukui, Norihito
Lee, Seung Kyu
Kato, Kenichi
Shimizu, Daiki  kyouindb  KAKEN_id  orcid https://orcid.org/0000-0002-2053-3483 (unconfirmed)
Tanaka, Takayuki  kyouindb  KAKEN_id  orcid https://orcid.org/0000-0001-8018-7984 (unconfirmed)
Lee, Sangsu
Yorimitsu, Hideki  kyouindb  KAKEN_id  orcid https://orcid.org/0000-0002-0153-1888 (unconfirmed)
Kim, Dongho
Osuka, Atsuhiro  kyouindb  KAKEN_id
Author's alias: 田中, 隆行
依光, 英樹
大須賀, 篤弘
Issue Date: 1-Mar-2016
Publisher: Royal Society of Chemistry
Journal title: Chemical Science
Volume: 7
Start page: 4059
End page: 4066
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 meso-meso linked dimer, which was further converted to a quadruply phenylene-fused meso-meso, 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 meso-meso, 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.
Rights: © 2016 The Royal Society of Chemistry. This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence.
URI: http://hdl.handle.net/2433/216557
DOI(Published Version): 10.1039/c5sc04748j
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