Photochemistry of covalently-linked multi-porphyrinic systems

Naoki Aratani, Atsuhiro Osuka, Hyun Sun Cho, Dongho Kim

Research output: Contribution to journalReview article

134 Citations (Scopus)

Abstract

Synthesis, structural characteristics, and optical and electrochemical properties of various covalently-linked porphyrin arrays are described. First, aromatic-spacer bridged diporphyrins were prepared in which the diporphyrin geometries were conformationally-restricted and thus suitable for detailed studies on the exciton coupling and the intramolecular energy and/or electron transfer reactions. Secondly, the Ag(I)-salt oxidation of 5,15-diaryl Zn(II) porphyrins provided meso-meso-linked Zn(II)-diporphyrins. This reaction is advantageous in light of its high regioselectivity and easy extension to longer porphyrin arrays. The doubling reaction was repeated up to the synthesis of a discrete 128-mer, which is, to the best of our knowledge, the longest man-made molecule. Finally, the oxidation of meso-meso-linked Zn(II) porphyrin arrays with a combination of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and Sc(III)(OTf)3 produced fused porphyrin arrays with full π-conjugation, which displayed extremely small HOMO-LUMO gaps that reach into the infrared region.

Original languageEnglish
Pages (from-to)25-52
Number of pages28
JournalJournal of Photochemistry and Photobiology C: Photochemistry Reviews
Volume3
Issue number1
DOIs
Publication statusPublished - 2002

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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