Multifunctional Homopolymers: Postpolymerization Modification via Sequential Nucleophilic Aromatic Substitution

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• 作者：Tomohiro Kubo ; C. Adrian Figg ; Jeremy L. Swartz ; William L. A. Brooks ; Brent S. Sumerlin
• 刊名：Macromolecules
• 出版年：2016
• 出版时间：March 22, 2016
• 年：2016
• 卷：49
• 期：6
• 页码：2077-2084
• 全文大小：506K
• ISSN：1520-5835

文摘

Despite recent progress for efficient and precise synthesis of functional polymers, few reports describe postpolymerization functionalization strategies for the controlled incorporation of multiple pendent groups per repeat unit. Cyanuric chloride, or 2,4,6-trichloro-1,3,5-triazine (TCT), offers a facile method to introduce distinct pendent functionalities. An acrylamide monomer containing a triazine ring with two electrophilic sites was prepared from TCT and polymerized via reversible addition–fragmentation chain transfer (RAFT) polymerization. Subsequent nucleophilic aromatic substitution reactions using a combination of amine and thiol nucleophiles introduced two functionalities into each repeat unit of the RAFT-derived polymers. The success of each postpolymerization modification reaction was confirmed by ¹H NMR spectroscopy and size-exclusion chromatography, and small molecule model studies corroborated the high chemoselectivity of the nucleophilic aromatic substitution reactions. This postpolymerization modification strategy based on TCT enables a facile and efficient synthesis of multifunctional homopolymers.