Phthalimide-Containing Acrylic Monomers for Postpolymerization Modification

N-Phthalimidyl acrylate (1) and N-phthalimidyl methacrylate (2) are acrylate and methacrylate monomers useful for postpolymerization modification. In polymers containing units derived from 1 or 2, the phthalimide group undergoes reduction via single-electron transfer (SET) from a catalyst, followed by decarboxylation and hydrogenation with a hydrogen donor, converting into ethylene or propylene units, respectively.¹),²) In addition, other postpolymerization modifications such as alkene addition via decarboxylation,³) nitroxide radical coupling,³) and phosphonylation via radical-polar crossover (RPC) following decarboxylation⁴) have also been reported. These reactions enable the synthesis of copolymers with structures that are difficult to access using conventional methods. Copolymers of 2 with methyl methacrylate have also been reported to depolymerize into methyl methacrylate through beta-scission under various conditions,⁵),⁶) attracting attention for polymer recycling.

Related products

• TCI P3351 55484-53-2 1,3-Dioxoisoindolin-2-yl Acrylate
• TCI P3350 72299-96-8 1,3-Dioxoisoindolin-2-yl Methacrylate
• TCI S0814 38862-24-7 N-Succinimidyl Acrylate
• TCI S0812 38862-25-8 N-Succinimidyl Methacrylate

References

1. Ethylene-Free Synthesis of Polyethylene Copolymers and Block Copolymers. S. Frech et al., P. Theato, Macromolecules 2021, 54, 9937.
2. Photoinduced SET to access olefin-acrylate copolymers. J. B. Garrison et al., B. S. Sumerlin, Polym. Chem. 2022, 13, 982.
3. Decarboxylation of Poly[N-(acryloyloxy)phthalimide] as a Versatile Tool for Postpolymerization Modification. S. Frech et al., Macromol. Rapid Commun. 2022, 43, 2200068.
4. Organophotoredox-Catalyzed Postfunctionalization of Poly(methacrylate) Derivatives via Radical-Polar Crossover Phosphonylation. T. Tamano et al., Angew. Chem. Int. Ed. 2025, 64, e202507572.
5. Bulk Depolymerization of Methacrylate Polymers via Pendent Group Activation. R. W. Hughes et al., J. Am. Chem. Soc. 2024, 146, 6217.
6. Backbone Degradation of Polymethacrylates via Metal-Free Ambient-Temperature Photoinduced Single-Electron Transfer. J. B. Garrison et al., ACS Macro Lett. 2022, 11, 441.

Source

• TCI Product Highlights: www.tcichemicals.com/ID/en/product/tci-topics/ProductHighlights_20260112
• TCI product page P3351: tcichemicals.com/ID/en/p/P3351

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