Palladium-catalyzed direct phenylation of perylene: Structural and optical properties of 3,4,9-triphenylperylene and 3,4,9,10-tetraphenylperylene

Katsuaki Kawasumi, Kenji Mochida, Yasutomo Segawa, Kenichiro Itami

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

We have developed one-step synthesis of multiphenylperylenes from perylene through palladium-catalyzed oxidative C-H/C-B coupling using phenylboroxin as a phenyl source. The combination of Pd(OAc)2 as a catalyst and o-chloranil as an oxidant is the key for direct C-H arylation of perylene. The X-ray crystallography of 3,4,9-triphenylperylene (3) and 3,4,9,10- tetraphenylperylene (4) revealed twisted structures of perylene core caused by steric repulsion of neighboring phenyl groups. Compounds 3 and 4 showed red shift in both absorption and fluorescence spectra compared to perylene whereas absolute fluorescence quantum yields are similarly high (ΦF=0.94) .

Original languageEnglish
Pages (from-to)4371-4374
Number of pages4
JournalTetrahedron
Volume69
Issue number22
DOIs
Publication statusPublished - Jun 3 2013

Keywords

  • C-H arylation
  • Palladium catalyst
  • Perylene
  • Photophysical properties

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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