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Multicomponent Stereoselective Polymerizations toward Multifunctional AIE Polymers with α,β-Unsaturated Amidines

preprint
submitted on 28.04.2021, 03:24 and posted on 29.04.2021, 04:43 by xiang su, Niu Niu, Haoxuan Li, Ting Han, Dong Wang, Ben Zhong Tang

Heterochain polymers play an essential role in our daily lives due to their distinctive properties. Among various heteroatom-rich structures, amidine derivatives serve as a synthetically important and pharmacologically useful structural branch and have found wide applications in synthetic chemistry and biomedicine field. In this work, we developed a straightforward and powerful polymerization tool to access diverse heterochain polymers with α,β-unsaturated amidine units. The multicomponent electrophilic polymerizations of readily accessible diynes, disulfonyl azides, and N,N-dimethylformamide dimethyl acetal proceed efficiently at room temperature, producing amidine-containing polymers with high molecular weights (Mw up to 74500) in high yields within merely 1 h. Nuclear magnetic resonance spectra analysis revealed that all the obtained polymers are formed with excellent stereoselectiviy. The introduction of aggregation-induced emission (AIE) luminogen together with the inherent heteroatom-rich structure feature endow these polymers with multiple functionalities. The nanoaggregates of the diethylamino-substituted polymer show remarkable and reversible fluorescence response to acid and base, and the acid-fumed polymer thin film can be used as a sensitive and reusable fluorescent probe for detecting seafood spoilage. This polymer system can also be employed as a highly selective and sensitive Au3+ sensor, and efficient gold recovery can be achieved based on the excellent gold enrichment capability of the polymer. In addition, the AIE polymers can also be applied in lysosome-specific cell imaging with low cytotoxicity and excellent photostability.

History

Email Address of Submitting Author

sx2016311171@163.com

Institution

shenzhen university

Country

china

ORCID For Submitting Author

0000-0002-6346-7666

Declaration of Conflict of Interest

no

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ChemRxiv

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