Allyl-Functionalized Polysaccharides for 3D Printable Hydrogels Through Thiol–Ene Click Chemistry
This study presents the synthesis of allyl-functionalized polysaccharide carbamates (AFCs) with tailored water solubility designed for use in responsive hydrogels and 3D printing applications. A modular one-pot approach was employed to produce cellulose- and xylan-based AFCs, utilizing polysaccharid...
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| Format: | Article |
| Language: | English |
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MDPI AG
2025-02-01
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| Series: | Polysaccharides |
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| Online Access: | https://www.mdpi.com/2673-4176/6/1/13 |
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| author | Zakaria Atmani Tobias Steindorfer Rupert Kargl Karin Stana Kleinschek Thomas Heinze Martin Gericke |
| author_facet | Zakaria Atmani Tobias Steindorfer Rupert Kargl Karin Stana Kleinschek Thomas Heinze Martin Gericke |
| author_sort | Zakaria Atmani |
| collection | DOAJ |
| description | This study presents the synthesis of allyl-functionalized polysaccharide carbamates (AFCs) with tailored water solubility designed for use in responsive hydrogels and 3D printing applications. A modular one-pot approach was employed to produce cellulose- and xylan-based AFCs, utilizing polysaccharide phenyl carbonates as activated compounds. By fine-tuning the degree of substitution (DS) of functional groups, the water solubility and shear-thinning properties of AFCs were controlled to enhance the gelation and printability. AFC-based hydrogels could be obtained by rapid gelation induced without harmful catalysts through UV irradiation at 365 nm. The materials displayed highly porous and interconnected microstructures, as well as mechanical resilience and high swelling ratios. The hydrogel formation was characterized, and its crosslinking degree was calculated using HR-MAS NMR. The study demonstrated that gelation behavior was sensitive to the pH value, with optimal results under neutral or acidic conditions. Initial 3D printing trials confirmed the material’s rapid shaping capabilities, which is beneficial for biomedical applications and advanced manufacturing of stimuli-responsive materials. |
| format | Article |
| id | doaj-art-cb4749c51d4341ffbd8badcc8479419c |
| institution | OA Journals |
| issn | 2673-4176 |
| language | English |
| publishDate | 2025-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Polysaccharides |
| spelling | doaj-art-cb4749c51d4341ffbd8badcc8479419c2025-08-20T01:49:01ZengMDPI AGPolysaccharides2673-41762025-02-01611310.3390/polysaccharides6010013Allyl-Functionalized Polysaccharides for 3D Printable Hydrogels Through Thiol–Ene Click ChemistryZakaria Atmani0Tobias Steindorfer1Rupert Kargl2Karin Stana Kleinschek3Thomas Heinze4Martin Gericke5Centre of Excellence for Polysaccharide Research, Institute of Organic Chemistry and Macromolecular Chemistry, Friedrich Schiller University Jena, Humboldtstraße 10, 07743 Jena, GermanyInstitute for Chemistry and Technology of Biobased Systems (IBIOSYS), Graz University of Technology, Stremayrgasse 9, 8010 Graz, AustriaInstitute for Chemistry and Technology of Biobased Systems (IBIOSYS), Graz University of Technology, Stremayrgasse 9, 8010 Graz, AustriaInstitute for Chemistry and Technology of Biobased Systems (IBIOSYS), Graz University of Technology, Stremayrgasse 9, 8010 Graz, AustriaCentre of Excellence for Polysaccharide Research, Institute of Organic Chemistry and Macromolecular Chemistry, Friedrich Schiller University Jena, Humboldtstraße 10, 07743 Jena, GermanyCentre of Excellence for Polysaccharide Research, Institute of Organic Chemistry and Macromolecular Chemistry, Friedrich Schiller University Jena, Humboldtstraße 10, 07743 Jena, GermanyThis study presents the synthesis of allyl-functionalized polysaccharide carbamates (AFCs) with tailored water solubility designed for use in responsive hydrogels and 3D printing applications. A modular one-pot approach was employed to produce cellulose- and xylan-based AFCs, utilizing polysaccharide phenyl carbonates as activated compounds. By fine-tuning the degree of substitution (DS) of functional groups, the water solubility and shear-thinning properties of AFCs were controlled to enhance the gelation and printability. AFC-based hydrogels could be obtained by rapid gelation induced without harmful catalysts through UV irradiation at 365 nm. The materials displayed highly porous and interconnected microstructures, as well as mechanical resilience and high swelling ratios. The hydrogel formation was characterized, and its crosslinking degree was calculated using HR-MAS NMR. The study demonstrated that gelation behavior was sensitive to the pH value, with optimal results under neutral or acidic conditions. Initial 3D printing trials confirmed the material’s rapid shaping capabilities, which is beneficial for biomedical applications and advanced manufacturing of stimuli-responsive materials.https://www.mdpi.com/2673-4176/6/1/13polysaccharideschemical derivatizationhydrogelsthiol–ene click chemistry3D printing |
| spellingShingle | Zakaria Atmani Tobias Steindorfer Rupert Kargl Karin Stana Kleinschek Thomas Heinze Martin Gericke Allyl-Functionalized Polysaccharides for 3D Printable Hydrogels Through Thiol–Ene Click Chemistry Polysaccharides polysaccharides chemical derivatization hydrogels thiol–ene click chemistry 3D printing |
| title | Allyl-Functionalized Polysaccharides for 3D Printable Hydrogels Through Thiol–Ene Click Chemistry |
| title_full | Allyl-Functionalized Polysaccharides for 3D Printable Hydrogels Through Thiol–Ene Click Chemistry |
| title_fullStr | Allyl-Functionalized Polysaccharides for 3D Printable Hydrogels Through Thiol–Ene Click Chemistry |
| title_full_unstemmed | Allyl-Functionalized Polysaccharides for 3D Printable Hydrogels Through Thiol–Ene Click Chemistry |
| title_short | Allyl-Functionalized Polysaccharides for 3D Printable Hydrogels Through Thiol–Ene Click Chemistry |
| title_sort | allyl functionalized polysaccharides for 3d printable hydrogels through thiol ene click chemistry |
| topic | polysaccharides chemical derivatization hydrogels thiol–ene click chemistry 3D printing |
| url | https://www.mdpi.com/2673-4176/6/1/13 |
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