3 years ago

Iridium-Catalyzed Direct C−H Amidation Polymerization: Step-Growth Polymerization by C−N Bond Formation via C−H Activation to Give Fluorescent Polysulfonamides

Iridium-Catalyzed Direct C−H Amidation Polymerization: Step-Growth Polymerization by C−N Bond Formation via C−H Activation to Give Fluorescent Polysulfonamides
Tae-Lim Choi, Yoon-Jung Jang, Soon-Hyeok Hwang
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. Direct C−H amidation polymerization: The first polymerization to form C−N bonds by means of C−H activation has been developed. The polymerization is a green and atom-economical process to produce defect-free polysulfonamides with high molecular weights. The polysulfonamides emit blue light with high quantum yields and large Stokes shifts upon photoexcitation.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201707446

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