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Novel Fluorophores based on Regioselective Intramolecular Friedel–Crafts Acylation of the Pyrene Ring Using Triflic Acid
Author(s) -
JousselinOba Tanguy,
Sbargoud Kamal,
Vaccaro Gianfranco,
Meinardi Francesco,
Yassar Abderrahim,
Frigoli Michel
Publication year - 2017
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.201704116
Subject(s) - triflic acid , regioselectivity , pyrene , friedel–crafts reaction , intramolecular force , chemistry , acylation , ring (chemistry) , fluorescence , organic chemistry , photochemistry , combinatorial chemistry , medicinal chemistry , catalysis , physics , quantum mechanics
The extension of the pyrene ring from dimethyl 2,2′‐(pyrene‐1,6‐diyl)dibenzoate derivatives by an intramolecular Friedel–Crafts acylation can be realized in an efficient and regioselective manner using triflic acid as proton source. Naphtho‐tetracenone derivatives are obtained in high yields at room temperature while Bis‐tetracene‐diones are prepared upon heating. Both products display interesting fluorescence properties in the visible range with quantum yields varying from 50 to 60 %.