Trithiocarbonate-type RAFT Reagents for Precision Radical Polymerization

Reversible addition fragmentation chain transfer (RAFT) polymerization is one of the methods for precision radical polymerizations. As RAFT polymerization allows to maintain the concentration of propagating radicals living and low, it is possible to precisely control the molecular weight and molecular weight distribution of the target polymer.¹⁾ For this reason, RAFT polymerization has attracted considerable attention due to the need for research and development of highly functional materials in the industrial and medical fields. RAFT reagents (1, 2, 3, 4, 5, 6) shown below are trithiocarbonate-type initiators. These RAFT reagents have such features as elongation in both ends (1, 2),²⁾ elongation in one end (3, 4),³⁾ and water-solubility (1-3, 5), respectively.⁴⁾ In addition, 5 and 6 can be used as raw materials of RAFT reagents by adding alkyl radicals generated from azo initiators.⁵⁾

For example, 3 can be used for synthesis of amphiphilic AB-type diblock co-polymers.³⁾ By using styrene or butyl acrylate as a hydrophobic monomer, 2-(2-ethoxyethoxy)ethyl acrylate or acrylic acid as a hydrophilic monomer and 3 as a chain transfer agent, sequential precision radical polymerization gives block co-polymer whose size of hydrophobic and hydrophilic segments are unified. Such polymers enable organic dyes to be dispersed in aqueous media, and the viscosity and thermal stability can be controlled. Therefore, the polymers are expected to be applied to a dispersion suitable for inkjet.

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References

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• 2) Poly(N-isopropylacrylamide) hydrogels fabricated via click chemistry: well-defined α,ω-bis propargyl linear poly(N-isopropylacrylamide)s as crosslinkers
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• 3) Amphiphilic Polymers for Color Dispersion: Toward Stable and Low-Viscosity Inkjet Ink
  • T. Ohtake, H. Ito, N. Toyoda, Langmuir 2022, 38, 7618.
• 4) Synthesis of a water-soluble chain transfer agent and its application in gel dispersions
  • X. Zhang, Z. Yang, S. Liu, J. Wang, S. Liu, D. Bao, P. Zhang, J. Appl. Polym. Sci. 2024, 141, e55205. width="32">
• 5) CO₂-Activated Reversible Transition between Polymersomes and Micelles with AIE Fluorescence
  • D. Zhang, Y. Fan, H. Chen, S. Trépout, M.-H. Li, Angew. Chem. Int. Ed. 2019, 58, 10260.

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