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

doi:10.1016/j.tet.2013.01.037

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 journal › Article

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 (Φ_F=0.94) .

Original language	English
Pages (from-to)	4371-4374
Number of pages	4
Journal	Tetrahedron
Volume	69
Issue number	22
DOIs	https://doi.org/10.1016/j.tet.2013.01.037
Publication status	Published - Jun 3 2013
Externally published	Yes

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Keywords

C-H arylation
Palladium catalyst
Perylene
Photophysical properties

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Drug Discovery

Cite this

Kawasumi, K., Mochida, K., Segawa, Y., & Itami, K. (2013). Palladium-catalyzed direct phenylation of perylene: Structural and optical properties of 3,4,9-triphenylperylene and 3,4,9,10-tetraphenylperylene. Tetrahedron, 69(22), 4371-4374. https://doi.org/10.1016/j.tet.2013.01.037

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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) .",

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AU - Itami, Kenichiro

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10.1016/j.tet.2013.01.037