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

15 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
Externally publishedYes

Fingerprint

Perylene
Palladium
Structural properties
Optical properties
Fluorescence
X ray crystallography
X Ray Crystallography
Quantum yield
Oxidants
Catalysts

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Palladium-catalyzed direct phenylation of perylene : Structural and optical properties of 3,4,9-triphenylperylene and 3,4,9,10-tetraphenylperylene. / Kawasumi, Katsuaki; Mochida, Kenji; Segawa, Yasutomo; Itami, Kenichiro.

In: Tetrahedron, Vol. 69, No. 22, 03.06.2013, p. 4371-4374.

Research output: Contribution to journalArticle

Kawasumi, Katsuaki ; Mochida, Kenji ; Segawa, Yasutomo ; Itami, Kenichiro. / Palladium-catalyzed direct phenylation of perylene : Structural and optical properties of 3,4,9-triphenylperylene and 3,4,9,10-tetraphenylperylene. In: Tetrahedron. 2013 ; Vol. 69, No. 22. pp. 4371-4374.
@article{9aa8459dffbb4487a0018b7eae4ef86d,
title = "Palladium-catalyzed direct phenylation of perylene: Structural and optical properties of 3,4,9-triphenylperylene and 3,4,9,10-tetraphenylperylene",
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) .",
keywords = "C-H arylation, Palladium catalyst, Perylene, Photophysical properties",
author = "Katsuaki Kawasumi and Kenji Mochida and Yasutomo Segawa and Kenichiro Itami",
year = "2013",
month = "6",
day = "3",
doi = "10.1016/j.tet.2013.01.037",
language = "English",
volume = "69",
pages = "4371--4374",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "22",

}

TY - JOUR

T1 - Palladium-catalyzed direct phenylation of perylene

T2 - Structural and optical properties of 3,4,9-triphenylperylene and 3,4,9,10-tetraphenylperylene

AU - Kawasumi, Katsuaki

AU - Mochida, Kenji

AU - Segawa, Yasutomo

AU - Itami, Kenichiro

PY - 2013/6/3

Y1 - 2013/6/3

N2 - 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) .

AB - 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) .

KW - C-H arylation

KW - Palladium catalyst

KW - Perylene

KW - Photophysical properties

UR - http://www.scopus.com/inward/record.url?scp=84876688322&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84876688322&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2013.01.037

DO - 10.1016/j.tet.2013.01.037

M3 - Article

AN - SCOPUS:84876688322

VL - 69

SP - 4371

EP - 4374

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 22

ER -