4.8 Article

Synthesis of Arylated Perylene Bisimides through C-H Bond Cleavage under Ruthenium Catalysis

Journal

ORGANIC LETTERS
Volume 11, Issue 23, Pages 5426-5429

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol902271b

Keywords

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Funding

  1. MEXT, Japan [21685011]
  2. Iketani Science and Technology Foundation
  3. Ministry of Education, Science, and Technology of Korea [2008-8-1955]
  4. AFSOR/AOARD
  5. Ministry of Education, Science & Technology (MoST), Republic of Korea [R32-2008-000-10217-0] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
  6. National Research Foundation of Korea [2009-0093839, 과06A1503] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
  7. Grants-in-Aid for Scientific Research [21685011] Funding Source: KAKEN

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Treatment of perylene bisimide (PBI) with various arylboronates In the presence of a ruthenium catalyst provides tetraarylated PBIs at 2,5,8,11-positions in good yields with perfect regioselectivity. The electronic nature of the introduced aryl substituents has a significant impact on their optical and electronic properties. This protocol has been applied to the synthesis of a water-soluble emissive PBI derivative.

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