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 language | English |
|---|---|
| Pages (from-to) | 4371-4374 |
| Number of pages | 4 |
| Journal | Tetrahedron |
| Volume | 69 |
| Issue number | 22 |
| DOIs | |
| 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
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 journal › Article
}
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 -