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Sequential nucleophilic “click” reactions for functional amphiphilic homopolymers

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Abstract

Amphiphilic homopolymers with high densities of functional groups are synthetically challenging. Thiol–yne nucleophilic click reactions have been investigated to introduce multiple functional groups in polymers with high density. An electron deficient alkyne group bearing methacrylate monomer was polymerized using reversible addition–fragmentation chain-transfer (RAFT) polymerization. Subsequently, the electron deficient alkyne group on polymer side chain was readily reacted with a thiol reagent using triethylamine (TEA) as the organocatalyst. This reaction was found to be very efficient under mild conditions. The resultant homopolymer bearing thiol vinyl ether functional groups could perform a second thiol addition with a stronger base, such as triazabicyclodecene (TBD), to prepare multifunctional homopolymers. This stepwise addition process was monitored by 1H NMR as well as gel permeation chromatography. The fidelity of this method was demonstrated by attaching different functionalities, including both hydrophobic and hydrophilic moieties. Furthermore, these dual functionalized polymers bearing dithioacetal groups are sensitive to reactive oxygen species (ROS), which compromises the host–guest properties of the assembly in response to this stimulus. The ROS responsive polymers reported here may have potential use in therapeutic delivery.

Graphical abstract: Sequential nucleophilic “click” reactions for functional amphiphilic homopolymers

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Publication details

The article was received on 16 Sep 2018, accepted on 14 Nov 2018 and first published on 15 Nov 2018


Article type: Communication
DOI: 10.1039/C8PY01341A
Citation: Polym. Chem., 2019, Advance Article
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    Sequential nucleophilic “click” reactions for functional amphiphilic homopolymers

    H. He, B. Liu, M. Wang, R. W. Vachet and S. Thayumanavan, Polym. Chem., 2019, Advance Article , DOI: 10.1039/C8PY01341A

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