Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 24, Issue 34, Pages 8548-8552Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201801915
Keywords
azulenes; cations; non-alternant hydrocarbon; polycyclic aromatic hydrocarbon; transannulation
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Funding
- JSPS KAKENHI [JP15H05848, JP18H01977, JP18K14201]
- Tonen General Sekiyu Research & Development Encouragement Foundation
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Polycyclic aromatic hydrocarbons (PAHs) that incorporate either heptagons or pentagons consist of non-planar molecular structures with unusual optoelectronic properties, and the design of a relatively simple and efficient method to construct these highly fused -conjugated systems with odd-membered rings is in high demand. This work describes the use of silver(I) cations to promote the efficient synthesis of azulene-embedded PAH 2, which is a structural isomer of tribenzo[fg,ij,rst]pentaphene 3, via tandem oxidative transannulation between the phenyl and arylethynyl moieties. This method involves a carbophilic interaction of the silver(I) cation with the acetylene units, which facilitates an electron transfer in the initial step. The synthesized PAH 2 and the protonated cation 2HBF(4) were fully characterized by X-ray crystallographic analysis, electronic absorption, electrochemical measurement, and quantum chemical calculation. The azulene-embedded PAH 2 exhibited a low-energy absorption band and amphoteric redox events, which were characterized as non-alternant characteristics originating from the azulene unit.
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