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Electron‐Deficient Tetrabenzo‐Fused Pyracylene and Conversions into Curved and Planar π‐Systems Having Distinct Emission Behaviors
Author(s) -
Murata Michihisa,
Sugano Yasunori,
Wakamiya Atsushi,
Murata Yasujiro
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201503783
Subject(s) - chemistry , intramolecular force , tetracene , adduct , triptycene , reactivity (psychology) , aryne , photochemistry , excimer , ring (chemistry) , anthracene , stereochemistry , medicinal chemistry , organic chemistry , fluorescence , medicine , physics , alternative medicine , pathology , quantum mechanics
Polycyclic aromatic compounds containing fully unsaturated five‐membered ring(s) have been intensively studied because of their unique properties, which include high electron affinity and reactivity. Reported herein is an efficient route for the synthesis of tetrabenzo‐fused pyracylene, which comprises pyracylene and tetracene segments, using intramolecular oxidative CH coupling. It was shown to possess high electron affinity and was found to undergo addition reactions with n ‐butyllithium or benzyne. These reactions led to either a 1,4‐addition compound or triptycene‐type adduct with a curved or planar π‐system, respectively. Although these compounds exhibited similar sky‐blue emissions in a dilute solution, the emission band of the 1,4‐addition compound was significantly red‐shifted in the solid state and exhibited intense yellow emission attributable to the excimer, while the triptycene‐type adduct retained the intense blue color emission in the solid state.