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
Chemically triggered life control of “smart” hydrogels through click and declick reactions
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.
hydrogels / degradation / synthesis / regeneration
[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.
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
|
/
〈 | 〉 |