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

Bibliographic Information

Other Title

• Regioselective phenylene-fusion reactions of Ni(<scp>ii</scp>)-porphyrins controlled by an electron-withdrawing meso-substituent

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.

Journal

• Chemical Science

  Chemical Science 7 4059-4066, 2016-03-01

  Royal Society of Chemistry (RSC)

Keywords

• General Chemistry

Details

• CRID: 1050282810814933376
• NII Article ID: 120005841418
• NII Book ID: AA12555653
• ISSN: 20416539
• ISSN: 20416520
• DOI: 10.1039/c5sc04748j
• HANDLE: 2433/216557
• Web Site: http://pubs.rsc.org/en/content/articlepdf/2016/SC/C5SC04748J
• Text Lang: en
• Article Type: journal article
• Data Source:
  • IRDB
  • Crossref
  • CiNii Articles
  • KAKEN