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Updated: Sep 21, 2025

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
Published on: February 6, 2020
Azo Coupling Reaction Induced Macromolecular Self-Assembly in Aqueous Solution
Shang Li1, Jilei Wang1, Jiajia Shen1
1Department of Chemical Engineering, Key Laboratory of Advanced Materials (MOE), Tsinghua University, Beijing, 100084, China.
Abstract:
This communication reported azo coupling reaction induced macromolecular self-assembly in aqueous solution. Diblock copolymer (PEG-b-PSNHBoc) consisting of a hydrophilic PEG block, and a hydrophobic N-Boc protected poly(p-vinylaniline) block was synthesized by RAFT polymerization. Then double hydrophilic diblock copolymer (PEG-b-PSN2+) composed of PEG and PS based macromolecular diazonium salts was prepared by the diazotization of PEG-b-PSNH2, which was obtained by deprotection of PEG-b-PSNHBoc. As N,N-dimethylaniline was gradually added into the freshly prepared PEG-b-PSN2+ aqueous solution, the azo coupling reaction between N,N-dimethylaniline and diazonium salts took place, which would lead to the generation of azobenzene pendants. Due to the poor solubility of azobenzene pendants in water, the formed hydrophobic polymeric chains aggregated to form the self-assembly colloidal particles. By incorporating a fluorescent group into the aniline, the aggregates formed through azo coupling reaction induced macromolecular self-assembly showed enzyme-triggered fluorescent behaviors.
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