Palladium-catalyzed cycloisomerizations of diarylacetylenes: Synthesis, structures, and physical properties of highly substituted naphthalenes and 8,8 a-dihydrocyclopenta[a]indenes

Tsun Cheng Wu, Chia Cheng Tai, Hsin Chieh Tiao, Yu Ting Chang, Chia Chun Liu, Ching Hsiu Li, Cheng Hao Huang, Ming Yu Kuo, Yao-Ting Wu

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13 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)7220-7227
Number of pages8
JournalChemistry - A European Journal
Volume17
Issue number26
DOIs
Publication statusPublished - 2011 Jun 20

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

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