Chemically triggered life control of “smart” hydrogels through click and declick reactions

Xing Feng, Meiqing Du, Hongbei Wei, Xiaoxiao Ruan, Tao Fu, Jie Zhang, Xiaolong Sun

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Front. Chem. Sci. Eng. ›› 2022, Vol. 16 ›› Issue (9) : 1399-1406. DOI: 10.1007/s11705-022-2149-z
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Chemically triggered life control of “smart” hydrogels through click and declick reactions

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Abstract

The degradation of polymeric materials is recognized as one of the goals to be fulfilled for the sustainable economy. In this study, a novel methodology was presented to synthesize multiple highly cross-linked polymers (i.e., hydrogels) through amine–thiol scrambling under mild conditions. Amine-terminated poly(ethylene glycol) (PEG-NH2) was reacted with the representative conjugate acceptors to synthesize hydrogels in organic and aqueous solutions, respectively. The materials above exhibited high water-swelling properties, distributed porous structures, as well as prominent mechanical strengths. It is noteworthy that the mentioned hydrogels could be degraded efficiently in hours to release the original coupling partner, which were induced by ethylene diamine at ambient temperature through amine-amine metathesis. The recovered PEG-NH2 reagent could be employed again to regenerate hydrogels. Due to the multiple architectures and functions in polymeric synthesis, degradation and regeneration, a new generation of “smart” materials is revealed.

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Keywords

hydrogels / degradation / synthesis / regeneration

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Xing Feng, Meiqing Du, Hongbei Wei, Xiaoxiao Ruan, Tao Fu, Jie Zhang, Xiaolong Sun. Chemically triggered life control of “smart” hydrogels through click and declick reactions. Front. Chem. Sci. Eng., 2022, 16(9): 1399‒1406 https://doi.org/10.1007/s11705-022-2149-z

References

[1]
Liu X, Liu J, Lin S, Zhao X. Hydrogel machines. Materials Today, 2020, 36( 25): 102– 124
CrossRef Google scholar
[2]
Hockaday L A, Kang K H, Colangelo N W, Cheung P Y, Duan B, Malone E, Wu J, Girardi L N, Bonassar L J, Lipson H. . Rapid 3D printing of anatomically accurate and mechanically heterogeneous aortic valve hydrogel scaffolds. Biofabrication, 2012, 4( 3): 035005– 035017
CrossRef Google scholar
[3]
Buwalda S J, Boere K W, Dijkstra P J, Feijen J, Vermonden T, Hennink W E. Hydrogels in a historical perspective: from simple networks to smart materials. Journal of Controlled Release, 2014, 190( 21): 254– 273
CrossRef Google scholar
[4]
Perez-San Vicente A, Peroglio M, Ernst M, Casuso P, Loinaz I, Grande H J, Alini M, Eglin D, Dupin D. Self-healing dynamic hydrogel as injectable shock-absorbing artificial nucleus pulposus. Biomacromolecules, 2017, 18( 8): 2360– 2370
CrossRef Google scholar
[5]
Cheng H, Yue K, Kazemzadeh-Narbat M, Liu Y, Khalilpour A, Li B, Zhang Y S, Annabi N, Khademhosseini A. Mussel-inspired multifunctional hydrogel coating for prevention of infections and enhanced osteogenesis. ACS Applied Materials & Interfaces, 2017, 9( 13): 11428– 11439
CrossRef Google scholar
[6]
Zhao X, Wu H, Guo B, Dong R, Qiu Y, Ma P X. Antibacterial anti-oxidant electroactive injectable hydrogel as self-healing wound dressing with hemostasis and adhesiveness for cutaneous wound healing. Biomaterials, 2017, 122( 4): 34– 47
CrossRef Google scholar
[7]
Li J, Mooney D J. Designing hydrogels for controlled drug delivery. Nature Reviews Materials, 2016, 1( 12): 1– 17
CrossRef Google scholar
[8]
Choi M, Choi J W, Kim S, Nizamoglu S, Hahn S K, Yun S H. Light-guiding hydrogels for cell-based sensing and optogenetic synthesis in vivo. Nature Photonics, 2013, 7( 12): 987– 994
CrossRef Google scholar
[9]
Xu L, Chen K, Chen G Q, Kentish S E, Li G. Development of barium@alginate adsorbents for sulfate removal in lithium refining. Frontiers of Chemical Science and Engineering, 2020, 15( 1): 198– 207
CrossRef Google scholar
[10]
Huang Y, Li H, He X, Yang X, Li L, Liu S, Zou Z, Wang K, Liu J. Near-infrared photothermal release of hydrogen sulfide from nanocomposite hydrogels for anti-inflammation applications. Chinese Chemical Letters, 2020, 31( 3): 787– 791
CrossRef Google scholar
[11]
Guo Y, Bae J, Fang Z, Li P, Zhao F, Yu G. Hydrogels and hydrogel-derived materials for energy and water sustainability. Chemical Reviews, 2020, 120( 15): 7642– 7707
CrossRef Google scholar
[12]
Choi M, Humar M, Kim S, Yun S H. Step-index optical fiber made of biocompatible hydrogels. Advanced Materials, 2015, 27( 17): 4081– 4086
CrossRef Google scholar
[13]
Yan D, Liu S, Jia Y G, Mo L, Qi D, Wang J, Chen Y, Ren L. Responsive polypseudorotaxane hydrogels triggered by a compatible stimulus of CO2. Macromolecular Chemistry and Physics, 2019, 220( 12): 1900071– 1900076
CrossRef Google scholar
[14]
Chalmers E, Li Y, Liu X. Molecular tailoring to improve polypyrrole hydrogels’ stiffness and electrochemical energy storage capacity. Frontiers of Chemical Science and Engineering, 2019, 13( 4): 684– 694
CrossRef Google scholar
[15]
Yang C, Suo Z. Hydrogel ionotronics. Nature Reviews Materials, 2018, 3( 6): 125– 142
CrossRef Google scholar
[16]
Arslan H, Nojoomi A, Jeon J, Yum K 3rd. Printing of anisotropic hydrogels with bioinspired motion. Advancement of Science, 2019, 6( 2): 1800703– 1800711
CrossRef Google scholar
[17]
Gao Y, Gu S, Jia F, Gao G. A skin-matchable, recyclable and biofriendly strain sensor based on a hydrolyzed keratin-containing hydrogel. Journal of Materials Chemistry A, 2020, 8( 45): 24175– 24183
CrossRef Google scholar
[18]
Correa S, Grosskopf A K, Lopez Hernandez H, Chan D, Yu A C, Stapleton L M, Appel E A. Translational applications of hydrogels. Chemical Reviews, 2021, 18( 14): 11385– 11457
CrossRef Google scholar
[19]
Glowacki J, Mizuno S. Collagen scaffolds for tissue engineering. Biopolymers, 2008, 89( 5): 338– 344
CrossRef Google scholar
[20]
Haque M A, Kurokawa T, Gong J P. Super tough double network hydrogels and their application as biomaterials. Polymer, 2012, 53( 9): 1805– 1822
CrossRef Google scholar
[21]
Yue Y, Wang X, Wu Q, Han J, Jiang J. Highly recyclable and super-tough hydrogel mediated by dual-functional TiO2 nanoparticles toward efficient photodegradation of organic water pollutants. Journal of Colloid and Interface Science, 2020, 564( 5): 99– 112
CrossRef Google scholar
[22]
Liu Y, Sun Q, Yang X, Liang J, Wang B, Koo A, Li R, Li J, Sun X. High-performance and recyclable Al-air coin cells based on eco-friendly chitosan hydrogel membranes. ACS Applied Materials & Interfaces, 2018, 10( 23): 19730– 19738
CrossRef Google scholar
[23]
Yuan T, Qu X, Cui X, Sun J. Self-healing and recyclable hydrogels reinforced with in situ-formed organic nanofibrils exhibit simultaneously enhanced mechanical strength and stretchability. ACS Applied Materials & Interfaces, 2019, 11( 35): 32346– 32353
CrossRef Google scholar
[24]
Chamas A, Moon H, Zheng J, Qiu Y, Tabassum T, Jang J H, Abu-Omar M, Scott S L, Suh S. Degradation rates of plastics in the environment. ACS Sustainable Chemistry & Engineering, 2020, 8( 9): 3494– 3511
CrossRef Google scholar
[25]
Delplace V, Nicolas J. Degradable vinyl polymers for biomedical applications. Nature Chemistry, 2015, 7( 10): 771– 784
CrossRef Google scholar
[26]
Ben Cheikh A, Chuche J, Manisse N, Pommelet J C, Netsch K P, Lorencak P, Wentrup C. Synthesis of α-cyano carbonyl compounds by flash vacuum thermolysis of (alkylamino)methylene derivatives of meldrum’s acid. Evidence for facile 1,3-shifts of alkylamino and alkylthio groups in imidoylketene intermediates. Journal of Organic Chemistry, 1991, 56( 3): 970– 975
CrossRef Google scholar
[27]
Sweidan K, Abu-Salem Q, Al-Sheikh A, Sheikha G. Novel derivatives of 1,3-dimethyl-5-methylenebarbituric acid. Letters in Organic Chemistry, 2009, 6( 8): 669– 672
CrossRef Google scholar
[28]
El-Zaatari B M, Ishibashi J S A, Kalow J A. Cross-linker control of vitrimer flow. Polymer Chemistry, 2020, 11( 33): 5339– 5345
CrossRef Google scholar
[29]
Diehl K L, Kolesnichenko I V, Robotham S A, Bachman J L, Zhong Y, Brodbelt J S, Anslyn E V. Click and chemically triggered declick reactions through reversible amine and thiol coupling via a conjugate acceptor. Nature Chemistry, 2016, 8( 10): 968– 973
CrossRef Google scholar
[30]
Meadows M K, Sun X, Kolesnichenko I V, Hinson C M, Johnson K A, Anslyn E V. Mechanistic studies of a “declick” reaction. Chemical Science (Cambridge), 2019, 10( 38): 8817– 8824
CrossRef Google scholar
[31]
Sun X, Chwatko M, Lee D H, Bachman J L, Reuther J F, Lynd N A, Anslyn E V. Chemically triggered synthesis, remodeling, and degradation of soft materials. Journal of the American Chemical Society, 2020, 142( 8): 3913– 3922
CrossRef Google scholar
[32]
Chang L, Wang C, Han S, Sun X, Xu F. Chemically triggered hydrogel transformations through covalent adaptable networks and applications in cell culture. ACS Macro Letters, 2021, 10( 7): 901– 906
CrossRef Google scholar
[33]
Wu T, Liang T, Hu W, Du M, Zhang S, Zhang Y, Anslyn E V, Sun X. Chemically triggered click and declick reactions: application in synthesis and degradation of thermosetting plastics. ACS Macro Letters, 2021, 10( 9): 1125– 1131
CrossRef Google scholar
[34]
Fang Y, Xu J, Gao F, Du X, Du Z, Cheng X, Wang H. Self-healable and recyclable polyurethane-polyaniline hydrogel toward flexible strain sensor. Composites Part B: Engineering, 2021, 219( 22): 108965– 108974
CrossRef Google scholar

Electronic Supplementary Material

Supplementary material is available in the online version of this article at https://dx.doi.org/10.1007/s11705-022-2149-z and is accessible for authorized users.

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