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 |
Keywords
- C-H arylation
- Palladium catalyst
- Perylene
- Photophysical properties
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry
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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