In this research, we designed a novel pyrazole–carbodithioate-based chain transfer agent bearing an aldehyde group (CTA-CHO) to expend the synthetic utility of the end-functionalized polymers and the potential modification based on the aldehyde reactivity. The CTA-CHO was subjected to the reversible addition-fragmentation chain-transfer (RAFT) radical polymerization of vinyl monomers to furnish a well-defined polymers end-functionalized with aldehyde moiety. In order to showcase the reactivity and thus utility of polymers end-functionalized with aldehyde units, postpolymerization modification were performed by employing multicomponent reactions (MCRs). As a result, a wide range of analysis results including size-exclusion chromatography (SEC), <sup>1</sup>H NMR, and FT-IR measurements revealed the high reactivity of aldehyde moiety under the catalyst-free Passerini three-components reaction. All in all, we succeeded in designing and using CTA-CHO for the synthesis of well-defined polymers end-functionalized polymers with aldehyde moiety. In addition, the chain end Passerini-three component reaction was revealed to proceed without the aid of additional activators nor catalysts, highlighting the synthetic benefits of the newly designed CTA-CHO.

Application of the Passerini three-component reaction for the chain end modification of end-functionalized polymers with aldehyde groups

ACS Spring Meeting 2021

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