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Thiol-ene derivatization of polycarbonates from 5-methylene-1,3-dioxane-2-one: an efficient and practical way to tune the surface biocompatibility of polycarbonate films

Polymer Journal (2025)Cite this article

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Abstract

Poly(trimethylene carbonate) (PTMC) is a biodegradable polymer that is widely utilized in biomedical fields because of the soft mechanical properties conferred by its low glass transition temperature. However, its application is limited by the lack of reactive sites on its backbone for chemical modifications. To overcome this limitation, a copolymer, poly(trimethylene carbonate-r-5-methylene-1,3-dioxane-2-one) (PTMC-r-PexTMC), was developed as a platform for postpolymerization functionalization. Using thiol-ene click chemistry, diol and carboxylic acid groups were grafted onto PTMC-r-PexTMC at levels ranging from 1 to 30 mol% to tailor its hydrophilicity and surface compatibility. Thermogravimetric and contact angle analyses revealed that both the thermal stability and hydrophilicity increased with the degree of functionalization. Importantly, copolymers containing 30 mol% diol units inhibited platelet adhesion more effectively than those with equivalent carboxylic acid content did, indicating that both hydrophilicity and surface charge influence biocompatibility. Further studies involving degradation in PBS and doxorubicin release confirmed the potential of these functional groups to modulate polymer performance. These findings highlight the value of surface modification in increasing the biocompatibility of polycarbonates for advanced medical applications.

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Acknowledgements

This work was supported financially by the Centre National de la Recherche Scientifique and the Université de Toulouse 3. This work was partly supported by the Suzuken Memorial Foundation and JSPS KAKENHI (JP24K01555). We are grateful for the fruitful discussions with Dr. Tsuyoshi Ando, Dr. Hiroaki Yoshida, Dr. Katsunori Tanaka, and Dr. Keita Okayama.

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Authors and Affiliations

  1. Division of Materials Science, Graduate School of Science and Technology, Nara Institute of Science and Technology, Nara, Japan

    Kamolchanok Sarisuta, Nalinthip Chanthaset & Hiroharu Ajiro

  2. Laboratoire Hétérochimie Fondamentale et Appliquée (UMR 5069), Université de Toulouse (UPS), CNRS, Toulouse, France

    Kamolchanok Sarisuta, Blanca Martín-Vaca, Didier Bourissou & Julien Monot

  3. Data Science Center, Nara Institute of Science and Technology, Nara, Japan

    Hiroharu Ajiro

  4. Medilux Research Center, Nara Institute of Science and Technology, Nara, Japan

    Hiroharu Ajiro

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  1. Kamolchanok Sarisuta
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Correspondence to Blanca Martín-Vaca, Didier Bourissou, Nalinthip Chanthaset or Hiroharu Ajiro.

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Sarisuta, K., Martín-Vaca, B., Bourissou, D. et al. Thiol-ene derivatization of polycarbonates from 5-methylene-1,3-dioxane-2-one: an efficient and practical way to tune the surface biocompatibility of polycarbonate films. Polym J (2025). https://doi.org/10.1038/s41428-025-01068-y

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