Chemistry - A European Journal p. 7220 - 7227 (2011)
Update date:2022-09-26
Topics:
Wu, Tsun-Cheng
Tai, Chia-Cheng
Tiao, Hsin-Chieh
Chang, Yu-Ting
Liu, Chia-Chun
Li, Ching-Hsiu
Huang, Cheng-Hao
Kuo, Ming-Yu
Wu, Yao-Ting
Depending on the electronic properties of their substituents, the major products generated by palladium-catalyzed cycloisomerizations of diarylalkynes are either highly substituted 8,8a-dihydrocyclopenta[a]indenes 3 or naphthalenes 4. The structures of these compounds were verified by X-ray crystallographic analysis. Many functional groups tolerated the reaction conditions evaluated in this study. The isotope-labeled experiments indicated that added water has a critical role in forming both classes of compounds. The photophysical and electrochemical properties of cycloadducts 3 and their analogues were systematically studied and compared with computational predictions based on density functional theory. Dihydrocyclopenta[a]indenes 3 in either solid or liquid form display strong luminescence, whereas cyclopenta[a]indene 11 j is practically nonfluorescent. The functional groups directly attached to the backbone of compound 3 significantly influenced physical properties. The steric effect arising from the aryl substituents caused different luminescence phenomena, including aggregation-induced and -enhanced emission. Copyright
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