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Palladium‐Catalyzed Cycloisomerizations of Diarylacetylenes: Synthesis, Structures, and Physical Properties of Highly Substituted Naphthalenes and 8,8 a‐Dihydrocyclopenta[ a ]indenes
Author(s) -
Wu TsunCheng,
Tai ChiaCheng,
Tiao HsinChieh,
Chang YuTing,
Liu ChiaChun,
Li ChingHsiu,
Huang ChengHao,
Kuo MingYu,
Wu YaoTing
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201100437
Subject(s) - indene , chemistry , palladium , catalysis , density functional theory , steric effects , aryl , electrochemistry , luminescence , photochemistry , computational chemistry , medicinal chemistry , stereochemistry , organic chemistry , materials science , alkyl , optoelectronics , electrode
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.