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
N1 - Funding Information:
This work was supported by the Funding Program for Next Generation World-Leading Researchers (JSPS). The Nagoya University Global COE Program in Chemistry and the MEXT Joint Project of Chemical Synthesis Core Research Institutions are also acknowledged for support. K.K. is the recipient of Leading Graduate School RA and JSPS research fellowship for young scientists. We thank Prof. Shigehiro Yamaguchi, Dr. Aiko Fukazawa, and Dr. Shohei Saito (Nagoya Univ.) for assistance in the measurement of photophysical properties.
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 -