Catalyst-Free Propiolamide-Based Amino-Yne Click Polymerization toward Degradable Polyamides

Polyamides, as a class of high-performance polymers, have been extensively employed in critical industrial sectors. However, their further development is constrained by challenges, including harsh reaction conditions, stringent monomer purity requirements, and environmental concerns due to degradation resistance. In this work, we successfully established a catalyst-free propiolamide-based amino-yne click polymerization with 100% atom economy and outstanding regioselectivity and stereoselectivity. Polyamides with a sole E-configuration and weight-average molecular weights (Mw, up to 14500) were obtained in excellent yields (up to 95%). Notably, the in situ generated enamine units from the click polymerization endow the polyamides with dynamic behavior, allowing them to be rapidly and controllably degraded upon the addition of monoamines at elevated temperature. Moreover, the incorporation of tetraphenylethylene (TPE) units endowed the resultant polyamide with aggregation-induced emission (AIE) characteristics, enabling highly specific and sensitive detection of Au3+ ions with a limit of detection of 2.101 × 10–7 M. Therefore, this work not only establishes a highly efficient catalyst-free propiolamide-based amino-yne click polymerization but also offers an innovative insight for the design and preparation of degradable and functional polyamides.