Visible Light-Induced Fabrication of a Clickable Cu(I) Benzophenone Dicarboxylate Polymer - Polyacrylamide Hydrogel Composite
Published 02/03/2024
Keywords
- hydrogels,
- polyacrylamide,
- coordination polymers,
- light-induced polymerization,
- Type II photoinitiator
How to Cite
Copyright (c) 2024 Sena Ermiş, Mehmet Bilgehan Bilgiç, Barış Kışkan, Kerem Kaya
This work is licensed under a Creative Commons Attribution-NoDerivatives 4.0 International License.
Abstract
Hydrogels are a class of hydrophilic polymers that have been widely applied in numerous fields, most of which are related to bioengineering such as tissue scaffolds, biosensing and antibacterial activity. Especially, polyacrylamide (PAAm) hydrogels, due to their superior stability, non-toxicity and viscoelasticity, have been extensively studied over the last two decades in different bio-related applications. Coordination polymers (CPs) including metal-organic frameworks (MOFs), due to tunability of the organic linkers and metal ions, and their robustness, have been incorporated with hydrogels in order to improve the physical/chemical properties of the final composite. Herein, we report for the first time, the use of a photoactive Cu(I) coordination polymer, as Norrish type II photoinitiator, for the visible light-induced in situ fabrication of a clickable and highly-crosslinked Cu(I)CP-PAAm hydrogel composite using water as the solvent. Due to the high stability of the Cu(I)CP in water, that was demonstrated by powder X-ray studies, the release of copper ions was observed to occur after more than two days. Another advantage of the developed synthetic method, is the possibility to readily post-modify the hydrogel-composite by employing an azide-functionalized polymer through internal copper-catalyzed azide-alkyne click reaction.
References
- Aakeröy, C. B., Baldrighi, M., Desper, J., Metrangolo, P., & Resnati, G. (2013). Supramolecular Hierarchy among Halogen-Bond Donors. Chemistry – A European Journal, 19(48), 16240-16247. https://doi.org/https://doi.org/10.1002/chem.201302162
- Abdurrahmanoglu, S., Cilingir, M., & Okay, O. (2011). Dodecyl methacrylate as a crosslinker in the preparation of tough polyacrylamide hydrogels. Polymer, 52(3), 694-699. https://doi.org/https://doi.org/10.1016/j.polymer.2010.12.044
- Ahmed, E. M. (2015). Hydrogel: Preparation, characterization, and applications: A review. Journal of Advanced Research, 6(2), 105-121. https://doi.org/https://doi.org/10.1016/j.jare.2013.07.006
- Al-Mahamad, L. L. G., El-Zubir, O., Smith, D. G., Horrocks, B. R., & Houlton, A. (2017). A coordination polymer for the site-specific integration of semiconducting sequences into DNA-based materials. Nature Communications, 8(1), 720. https://doi.org/10.1038/s41467-017-00852-6
- Aydınoğlu, D., Şen, S., Helvacıoğlu, E., Nugay, T., & Nugay, N. (2014). Tuning of heavy metal removal efficiency from water via micro algae/hydrogel composites. e-Polymers, 13. https://doi.org/10.1515/epoly-2013-0116
- Bilgic, M. B., Kaya, K., Orakdogen, N., & Yagci, Y. (2022). Light-induced synthesis and characterization of “Clickable” polyacrylamide hydrogels. European Polymer Journal, 167, 111062. https://doi.org/https://doi.org/10.1016/j.eurpolymj.2022.111062
- Cao, H., Duan, L., Zhang, Y., Cao, J., & Zhang, K. (2021). Current hydrogel advances in physicochemical and biological response-driven biomedical application diversity. Signal Transduction and Targeted Therapy, 6(1), 426. https://doi.org/10.1038/s41392-021-00830-x
- Ceylan, D., Ozmen, M. M., & Okay, O. (2006). Swelling–deswelling kinetics of ionic poly(acrylamide) hydrogels and cryogels. Journal of Applied Polymer Science, 99(1), 319-325. https://doi.org/https://doi.org/10.1002/app.22023
- Ciftci, M., Kahveci, M. U., Yagci, Y., Allonas, X., Ley, C., & Tar, H. (2012). A simple route to synthesis of branched and cross-linked polymers with clickable moieties by photopolymerization [10.1039/C2CC35607D]. Chemical Communications, 48(82), 10252-10254. https://doi.org/10.1039/C2CC35607D
- Dsouza, A., Constantinidou, C., Arvanitis, T. N., Haddleton, D. M., Charmet, J., & Hand, R. A. (2022). Multifunctional Composite Hydrogels for Bacterial Capture, Growth/Elimination, and Sensing Applications. ACS Appl Mater Interfaces, 14(42), 47323-47344. https://doi.org/10.1021/acsami.2c08582
- Engel, E. R., & Scott, J. L. (2020). Advances in the green chemistry of coordination polymer materials [10.1039/D0GC01074J]. Green Chemistry, 22(12), 3693-3715. https://doi.org/10.1039/D0GC01074J
- Gün Gök, Z., & Inal, M. (2022). Effective Removing of Remazol Black B by the Polyacrylamide Cryogels Modified with Polyethyleneimine. Journal of Polymers and the Environment, 30. https://doi.org/10.1007/s10924-021-02187-2
- Heo, J., & Crooks, R. M. (2005). Microfluidic biosensor based on an array of hydrogel-entrapped enzymes. Anal Chem, 77(21), 6843-6851. https://doi.org/10.1021/ac0507993
- Hou, X., Sun, J., Lian, M., Peng, Y., Jiang, D., Xu, M., Li, B., & Xu, Q. (2023). Emerging Synthetic Methods and Applications of MOF-Based Gels in Supercapacitors, Water Treatment, Catalysis, Adsorption, and Energy Storage. Macromolecular Materials and Engineering, 308(2), 2200469. https://doi.org/https://doi.org/10.1002/mame.202200469
- Kalayci, K., Frisch, H., Truong, V. X., & Barner-Kowollik, C. (2020). Green light triggered [2+2] cycloaddition of halochromic styrylquinoxaline—controlling photoreactivity by pH. Nature Communications, 11(1), 4193. https://doi.org/10.1038/s41467-020-18057-9
- Kaya, K. (2023). A green and fast method for PEDOT: Photoinduced step-growth polymerization of EDOT. Reactive and Functional Polymers, 182, 105464. https://doi.org/https://doi.org/10.1016/j.reactfunctpolym.2022.105464
- Kocaarslan, A., Kaya, K., Jockusch, S., & Yagci, Y. (2022). Phenacyl Bromide as a Single-Component Photoinitiator: Photoinduced Step-Growth Polymerization of N-Methylpyrrole and N-Methylindole. Angewandte Chemie International Edition, 61(36), e202208845. https://doi.org/https://doi.org/10.1002/anie.202208845
- Lim, J. Y. C., Goh, L., Otake, K.-i., Goh, S. S., Loh, X. J., & Kitagawa, S. (2023). Biomedically-relevant metal organic framework-hydrogel composites [10.1039/D2BM01906J]. Biomaterials Science, 11(8), 2661-2677. https://doi.org/10.1039/D2BM01906J
- Liu, S., Brunel, D., Noirbent, G., Mau, A., Chen, H., Morlet-Savary, F., Graff, B., Gigmes, D., Xiao, P., Dumur, F., & Lalevée, J. (2021). New multifunctional benzophenone-based photoinitiators with high migration stability and their applications in 3D printing [10.1039/D0QM00885K]. Materials Chemistry Frontiers, 5(4), 1982-1994. https://doi.org/10.1039/D0QM00885K
- Murtezi, E., Ciftci, M., & Yagci, Y. (2014). Synthesis of Clickable Hydrogels and Linear Polymers by Type II Photoinitiation. Polymer International, 64. https://doi.org/10.1002/pi.4786
- Nguyen, K. T., & West, J. L. (2002). Photopolymerizable hydrogels for tissue engineering applications. Biomaterials, 23(22), 4307-4314. https://doi.org/https://doi.org/10.1016/S0142-9612(02)00175-8
- Norioka, C., Inamoto, Y., Hajime, C., Kawamura, A., & Miyata, T. (2021). A universal method to easily design tough and stretchable hydrogels. NPG Asia Materials, 13(1), 34. https://doi.org/10.1038/s41427-021-00302-2
- Orakdogen, N., & Okay, O. (2006). Reentrant conformation transition in poly(N,N-dimethylacrylamide) hydrogels in water–organic solvent mixtures. Polymer, 47(2), 561-568. https://doi.org/https://doi.org/10.1016/j.polymer.2005.11.066
- Qin, H., Li, F., Wang, D., Lin, H., & Jin, J. (2016). Organized Molecular Interface-Induced Noncrystallizable Polymer Ultrathin Nanosheets with Ordered Chain Alignment. ACS Nano, 10(1), 948-956. https://doi.org/10.1021/acsnano.5b06149
- Samav, Y., Demir, S., Solmaz, G., Tuncer, C., & Erer, H. (2023). Construction of Novel Co(II) Coordination Polymers-Hydrogel Composites for Dye Adsorption. Journal of Inorganic and Organometallic Polymers and Materials, 1-12. https://doi.org/10.1007/s10904-023-02882-8
- Sanchez-Rexach, E., Johnston, T. G., Jehanno, C., Sardon, H., & Nelson, A. (2020). Sustainable Materials and Chemical Processes for Additive Manufacturing. Chemistry of Materials, 32(17), 7105-7119. https://doi.org/10.1021/acs.chemmater.0c02008
- Soto-Quintero, A., Romo-Uribe, Á., Bermúdez-Morales, V. H., Quijada-Garrido, I., & Guarrotxena, N. (2017). 3D-Hydrogel Based Polymeric Nanoreactors for Silver Nano-Antimicrobial Composites Generation. Nanomaterials (Basel), 7(8). https://doi.org/10.3390/nano7080209
- Sun, W., Zhao, X., Webb, E., Xu, G., Zhang, W., & Wang, Y. (2023). Advances in metal–organic framework-based hydrogel materials: preparation, properties and applications [10.1039/D2TA08841J]. Journal of Materials Chemistry A, 11(5), 2092-2127. https://doi.org/10.1039/D2TA08841J
- Tabak, T., Kaya, K., Isci, R., Ozturk, T., Yagci, Y., & Kiskan, B. Combining Step-Growth and Chain-Growth Polymerizations in One Pot: Light-Induced Fabrication of Conductive Nanoporous PEDOT-PCL Scaffold. Macromolecular rapid communications, n/a(n/a), 2300455. https://doi.org/https://doi.org/10.1002/marc.202300455
- Taghipour, Y. D., Hokmabad, V. R., Del Bakhshayesh, A. R., Asadi, N., Salehi, R., & Nasrabadi, H. T. (2020). The Application of Hydrogels Based on Natural Polymers for Tissue Engineering. Curr Med Chem, 27(16), 2658-2680. https://doi.org/10.2174/0929867326666190711103956
- Tao, B., Lin, C., Deng, Y., Yuan, Z., Shen, X., Chen, M., He, Y., Peng, Z., Hu, Y., & Cai, K. (2019). Copper-nanoparticle-embedded hydrogel for killing bacteria and promoting wound healing with photothermal therapy. J Mater Chem B, 7(15), 2534-2548. https://doi.org/10.1039/c8tb03272f
- Terzyk, A. P., Bieniek, A., Bolibok, P., Wiśniewski, M., Ferrer, P., da Silva, I., & Kowalczyk, P. (2019). Stability of coordination polymers in water: state of the art and towards a methodology for nonporous materials. Adsorption, 25(1), 1-11. https://doi.org/10.1007/s10450-018-9991-9
- Uygun, M., Kahveci, M. U., Odaci, D., Timur, S., & Yagci, Y. (2009). Antibacterial Acrylamide Hydrogels Containing Silver Nanoparticles by Simultaneous Photoinduced Free Radical Polymerization and Electron Transfer Processes. Macromolecular Chemistry and Physics, 210(21), 1867-1875. https://doi.org/https://doi.org/10.1002/macp.200900296
- Vigata, M., Meinert, C., Hutmacher, D. W., & Bock, N. (2020). Hydrogels as Drug Delivery Systems: A Review of Current Characterization and Evaluation Techniques. Pharmaceutics, 12(12). https://doi.org/10.3390/pharmaceutics12121188
- Wang, Y., Borthwell, R. M., Hori, K., Clarkson, S., Blumstein, G., Park, H., Hart, C. M., Hamad, C. D., Francis, K. P., Bernthal, N. M., & Phillips, K. S. (2022). In vitro and in vivo methods to study bacterial colonization of hydrogel dermal fillers. J Biomed Mater Res B Appl Biomater, 110(8), 1932-1941. https://doi.org/10.1002/jbm.b.35050
- Xiao, J., Chen, S., Yi, J., Zhang, H., & Ameer, G. A. (2017). A Cooperative Copper Metal-Organic Framework-Hydrogel System Improves Wound Healing in Diabetes. Adv Funct Mater, 27(1). https://doi.org/10.1002/adfm.201604872
- Yilmaz, G., Kahveci, M., & Yagci, Y. (2011). A One Pot, One Step Method for the Preparation of Clickable Hydrogels by Photoinitiated Polymerization. Macromolecular rapid communications, 32, 1906-1909. https://doi.org/10.1002/marc.201100470
- You, S., Xiang, Y., Qi, X., Mao, R., Cai, E., Lan, Y., Lu, H., Shen, J., & Deng, H. (2022). Harnessing a biopolymer hydrogel reinforced by copper/tannic acid nanosheets for treating bacteria-infected diabetic wounds. Materials Today Advances, 15, 100271. https://doi.org/https://doi.org/10.1016/j.mtadv.2022.100271
- Yu, S., Duan, Y., Zuo, X., Chen, X., Mao, Z., & Gao, C. (2018). Mediating the invasion of smooth muscle cells into a cell-responsive hydrogel under the existence of immune cells. Biomaterials, 180, 193-205. https://doi.org/https://doi.org/10.1016/j.biomaterials.2018.07.022
- Zhan, Y., Fu, W., Xing, Y., Ma, X., & Chen, C. (2021). Advances in versatile anti-swelling polymer hydrogels. Materials Science and Engineering: C, 127, 112208. https://doi.org/https://doi.org/10.1016/j.msec.2021.112208
- Zhang, K., Shi, Z., Zhou, J., Xing, Q., Ma, S., Li, Q., Zhang, Y., Yao, M., Wang, X., Li, Q., Li, J., & Guan, F. (2018). Potential application of an injectable hydrogel scaffold loaded with mesenchymal stem cells for treating traumatic brain injury [10.1039/C7TB03213G]. Journal of Materials Chemistry B, 6(19), 2982-2992. https://doi.org/10.1039/C7TB03213G
- Zhou, W., Zi, L., Cen, Y., You, C., & Tian, M. (2020). Copper Sulfide Nanoparticles-Incorporated Hyaluronic Acid Injectable Hydrogel With Enhanced Angiogenesis to Promote Wound Healing. Front Bioeng Biotechnol, 8, 417. https://doi.org/10.3389/fbioe.2020.00417
- Zhu, X., Chen, Y., Xie, R., Zhong, H., Zhao, W., Liu, Y., & Yang, H. (2021). Rapid Gelling of Guar Gum Hydrogel Stabilized by Copper Hydroxide Nanoclusters for Efficient Removal of Heavy Metal and Supercapacitors. Front Chem, 9, 794755. https://doi.org/10.3389/fchem.2021.794755