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Iridium‐Catalyzed Direct C−H Amidation Polymerization: Step‐Growth Polymerization by C−N Bond Formation via C−H Activation to Give Fluorescent Polysulfonamides
Author(s) -
Jang YoonJung,
Hwang SoonHyeok,
Choi TaeLim
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201707446
Subject(s) - polymerization , chemistry , intramolecular force , iridium , photochemistry , photoexcitation , conjugated system , fluorescence , catalysis , sulfonyl , polymer chemistry , polymer , excited state , organic chemistry , physics , alkyl , quantum mechanics , nuclear physics
We report a powerful strategy for activation of C−H bonds to produce polysulfonamides by an atom‐economical and green method using iridium‐catalyzed direct C−H amidation polymerization (DCAP). After screening various directing groups, additives, silver salts, concentrations, and temperatures to optimize DCAP, high‐molecular‐weight (up to 149 kDa) and defect‐free polysulfonamides were synthesized from various bis‐sulfonyl azides. Although these polymers do not have conventional fluorescent conjugated cores, they emit blue light with large Stokes shifts and high quantum yields upon photoexcitation owing to an excited‐state intramolecular proton‐transfer process.