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

Norihito Fukui, Seung Kyu Lee, Kenichi Kato, Daiki Shimizu, Takayuki Tanaka, Sangsu Lee, Hideki Yorimitsu, Dongho Kim, Atsuhiro Osuka

Research output: Contribution to journalArticle

11 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)4059-4066
Number of pages8
JournalChemical Science
Volume7
Issue number7
DOIs
Publication statusPublished - 2016 Jul 1

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Porphyrins
Fusion reactions
Electrons
Bearings (structural)
Oxidation
Dimers
Ion exchange
Photons
Metals

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

Fukui, Norihito ; Lee, Seung Kyu ; Kato, Kenichi ; Shimizu, Daiki ; Tanaka, Takayuki ; Lee, Sangsu ; Yorimitsu, Hideki ; Kim, Dongho ; Osuka, Atsuhiro. / Regioselective phenylene-fusion reactions of Ni(II)-porphyrins controlled by an electron-withdrawing : Meso -substituent. In: Chemical Science. 2016 ; Vol. 7, No. 7. pp. 4059-4066.
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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 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.",
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Fukui, N, Lee, SK, Kato, K, Shimizu, D, Tanaka, T, Lee, S, Yorimitsu, H, Kim, D & Osuka, A 2016, 'Regioselective phenylene-fusion reactions of Ni(II)-porphyrins controlled by an electron-withdrawing: Meso -substituent', Chemical Science, vol. 7, no. 7, pp. 4059-4066. https://doi.org/10.1039/c5sc04748j

Regioselective phenylene-fusion reactions of Ni(II)-porphyrins controlled by an electron-withdrawing : Meso -substituent. / Fukui, Norihito; Lee, Seung Kyu; Kato, Kenichi; Shimizu, Daiki; Tanaka, Takayuki; Lee, Sangsu; Yorimitsu, Hideki; Kim, Dongho; Osuka, Atsuhiro.

In: Chemical Science, Vol. 7, No. 7, 01.07.2016, p. 4059-4066.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Regioselective phenylene-fusion reactions of Ni(II)-porphyrins controlled by an electron-withdrawing

T2 - Meso -substituent

AU - Fukui, Norihito

AU - Lee, Seung Kyu

AU - Kato, Kenichi

AU - Shimizu, Daiki

AU - Tanaka, Takayuki

AU - Lee, Sangsu

AU - Yorimitsu, Hideki

AU - Kim, Dongho

AU - Osuka, Atsuhiro

PY - 2016/7/1

Y1 - 2016/7/1

N2 - 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.

AB - 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.

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