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Triflic acid‐Mediated Expedient Synthesis of Benzo[ a ]fluorenes and Fluorescent Benzo[ a ]fluorenones
Author(s) -
Mandal Mou,
Balamurugan Rengarajan
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201701516
Subject(s) - chemistry , fluorene , triflic acid , cycloisomerization , fluorescence , triethyl orthoformate , cationic polymerization , naphthalene , friedel–crafts reaction , stereochemistry , photochemistry , organic chemistry , catalysis , polymer , physics , quantum mechanics
Fluorene‐based polyaromatic hydrocarbons are renowned compounds for materials applications. Herein, a straightforward route via in situ acetal formation has been presented to access benzo[ a ]fluorenes by a triflic acid promoted cationic cycloisomerization of enynones in presence of trimethyl orthoformate under metal‐free conditions. In the absence of trimethyl orthoformate, the same reaction results in benzo[ a ]fluorenones. All the synthesized benzo[ a ]fluorenones are highly fluorescent in solution phase with high Stokes shift while the corresponding benzo[ a ]fluorenes are not fluorescent.