Nucleobase-tackified Thioctic Acid-based Degradable and Recyclable Supramolecular Polymer Adhesives

Jiang Wu; Zan Hua; Guang-Ming Liu

doi:10.1007/s10118-025-3321-y

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Nucleobase-tackified Thioctic Acid-based Degradable and Recyclable Supramolecular Polymer Adhesives

RESEARCH ARTICLE | Updated：2025-07-15

- Nucleobase-tackified Thioctic Acid-based Degradable and Recyclable Supramolecular Polymer Adhesives
- Nucleobase-tackified Thioctic Acid-based Degradable and Recyclable Supramolecular Polymer Adhesives
- 高分子科学（英文） 2025年43卷第7期页码：1089-1095
- Affiliations：
  
  a.Hefei National Research Center for Physical Sciences at the Microscale, Department of Chemical Physics, University of Science and Technology of China, Hefei 230026, China
  b.The Key Laboratory of Functional Molecular Solids, Ministry of Education, and Department of Materials Chemistry, School of Chemistry and Materials Science, Anhui Normal University, Wuhu 241002, China
- Author bio：
  
  zanhua23@ahnu.edu.cn (Z.H.)
  gml@ustc.edu.cn (G.M.L.)
- Funds：
  
  This work was financially supported by the National Natural Science Foundation of China (Nos. 22273098, 22373003, 22103002 and 52033001) and the Key Project of Anhui Province Science and Technology Innovation Platform (No. 202305a12020030). Z. Hua also acknowledged the financial support from the Anhui Provincial Natural Science Foundation (No. 2408085Y004). This work was partially carried out at the Instruments Center for Physical Science, University of Science and Technology of China.;Electronic supplementary information (ESI) is available free of charge in the online version of this article at http://doi.org/10.1007/s10118-025-3321-y.
- DOI：10.1007/s10118-025-3321-y
  中图分类号：
- 收稿：2024-11-28，
  
  修回：2025-02-06，
  
  录用：2025-02-10，
  
  网络首发：2025-04-10，
  
  纸质出版：2025-07-01
- Accepted：
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Wu, J.; Hua, Z.; Liu, G. M. Nucleobase-tackified thioctic acid-based degradable and recyclable supramolecular polymer adhesives. Chinese J. Polym. Sci. 2025, 43, 1089–1095

Jiang Wu, Zan Hua, Guang-Ming Liu. Nucleobase-tackified Thioctic Acid-based Degradable and Recyclable Supramolecular Polymer Adhesives[J]. Chinese Journal of Polymer Science, 2025, 43(7): 1089-1095.
Wu, J.; Hua, Z.; Liu, G. M. Nucleobase-tackified thioctic acid-based degradable and recyclable supramolecular polymer adhesives. Chinese J. Polym. Sci. 2025, 43, 1089–1095 DOI： 10.1007/s10118-025-3321-y.

Jiang Wu, Zan Hua, Guang-Ming Liu. Nucleobase-tackified Thioctic Acid-based Degradable and Recyclable Supramolecular Polymer Adhesives[J]. Chinese Journal of Polymer Science, 2025, 43(7): 1089-1095. DOI： 10.1007/s10118-025-3321-y.

摘要

The construction of recyclable nucleobase-enhanced thioctic acid-based supramolecular polymer adhesives was achieved by reductive degradation and oxidative polymerization.

Abstract

Polymeric materials which can undergo controlled degradation and recycling are of great significance for a sustainable society. Although tremendous progress has been made in the degradation and recycling of both thermoplastic and thermoset plastics

the development of high-performance degradable polymer adhesives is rare. Here

we have prepared high-performance nucleobase-containing thioctic acid-based supramolecular polymer adhesives through free radical polymerization. The specific hydrogen-bonding interactions between complementary nucleobases greatly improve the weak cohesion of the thioctic acid-based polymers and enhance the environmental stability of the thioctic acid-based polymers simultaneously. Degradation of the nucleobase-containing thioctic acid-based supramolecular polymers is achieved by the reduction of the disulfide backbone

and the cycle of degradation and repolymerization is further achieved

via

oxidative polymerization. The adhesion strength of the nucleobase-containing thioctic acid-based supramolecular polymers after two cycles of degradation and repolymerization still reaches as high as 4.7±0.3 MPa. This work provides an approach for

the development of environmentally stable and high-performance degradable thioctic acid-based adhesives.

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references

Cui, C.; Liu, W. Recent advances in wet adhesives: adhesion mechanism, design principle and applications. Prog. Polym. Sci. 2021 , 116 , 101388..

Westerman, C. R.; McGill, B. C.; Wilker, J. J. Sustainably sourced components togenerate high-strength adhesives. Nature 2023 , 621 , 306−311..

Li, J., Celiz, A.D., Yang, J., Yang, Q., Wamala, I., Whyte, W., Seo, B.R., Vasilyev, N.V., Vlassak, J.J., Suo, Z., Mooney, D. J. Tough adhesives for diverse wet surfaces. Science 2017 , 357 , 378−381..

Li, X.; Wang, Z.; Li, W.; Sun, J. Superstr ong water-based supramolecular adhesives derived from poly(vinyl alcohol)/poly(acrylic acid) complexes. ACS Mater. Lett. 2021 , 3 , 875−882..

Droesbeke, M. A.; Aksakal, R.; Simula, A.; Asua, J. M.; Du Prez, F. E. Biobased acrylic pressure-sensitive adhesives. Prog. Polym. Sci. 2021 , 117 , 101396..

Chen, S.; Li, Z.; Wu, Y.; Mahmood, N.; Lortie, F.; Bernard, J.; Binder, W. H.; Zhu, J. Hydrogen-Bonded supramolecular polymer adhesives: straightforward synthesis and strong substrate interaction. Angew. Chem. Int. Ed. 2022 , 61 , e202203876..

Wu, J.; Lei, H.; Fang, X.; Wang, B.; Yang, G.; O’Reilly, R. K.; Wang, Z.; Hua, Z.; Liu, G. Instant strong and responsive underwater adhesion manifested by bioinspired supramolecular polymeric adhesives. Macromolecules 2022 , 55 , 2003−2013..

Zhao, M.; Wu, J.; Zeng, F.; Dong, Z.; Shen, X.; Hua, Z.; Liu, G. Wetting-enhanced adhesion of photo-polymerized supramolecular adhesives for both smooth and rough surfaces. Chem. Sci. 2024 , 15 , 6445−6453..

Kikkawa, K.; Sumiya, Y.; Okazawa, K.; Yoshizawa, K.; Itoh, Y.; Aida, T. Thiourea as a “polar hydrophobic” hydrogen-bonding motif: application to highly durable all-underwater adhesion. J. Am. Chem. Soc. 2024 , 146 , 21168−21175..

Li, C.; Dong, W.; Li, L.; Dou, Z.; Li, Y.; Wei, L.; Zhang, Q.; Fu, Q.; Wu, K. A strain-reinforcing elastomer adhesive with superior adhesive strength and toughness. Mater. Horiz. 2023 , 10 , 4183−4191..

Zhang, B.; Zhang, G.; Ma, C.; Zhang, G. Rational designed polymeric rigid cages for trapping bulky vegetable oils toward versatile bio-based adhesives. Adv. Funct. Mater . 2024, 2415944..

Van Lijsebetten, F.; Maiheu, T.; Winne, J. M.; Du Prez, F. E. Epoxy adhesives with reversible hardeners: controllable thermal debonding in bulk and at interfaces. Adv. Mater. 2023 , 35 , 2300802..

Jovanović, R.; Dubé, M. A. Emulsion-based pressure-sensitive adhesives: a review. J. Macromol. Sci., Part C: Polym. Rev. 2004 , 44 , 1−51..

Clarke, R. W.; Sandmeier, T.; Franklin, K. A.; Reich, D.; Zhang, X.; Vengallur, N.; Patra, T. K.; Tannenbaum, R. J.; Adhikari, S.; Kumar, S. K.; Rovis, T.; Chen, E. Y. Dynamic crosslinking compatibilizes immiscible mixed plastics. Nature 2023 , 616 , 731−739..

Bi, L.; Godwin, B.; Baran, M. J.; Nazir, R.; Wulff, J. E. A cleavable crosslinking strategy for commodity polymer functionalization and generation of reprocessable thermosets. Angew. Chem. Int. Ed. 2023 , 62 , e202304708..

Bao, C.; Yin, Y.; Ding, Y.; Liu, J.; Xu, Y.; Miao, R.; Liu, Z.; Duan, B.; Qin, Y.; Xin, Z. Chemically recyclable supramolecular thermosets toward strong and reusable hot-melt adhesives. Macromolecules 2023 , 56 , 6633−6643..

Zhong, L.; Hao, Y.; Zhang, J.; Wei, F.; Li, T.; Miao, M.; Zhang, D. Closed-loop recyclable fully bio-based epoxy vitrimers from ferulic acid-derived hyperbranched epoxy resin. Macromolecules 2022 , 55 , 595−607..

Kunduru, K. R.; Hogerat, R.; Ghosal, K.; Shaheen-Mualim, M.; Farah, S. Renewable polyol-based biodegradable polyesters as greener plastics for industrial applications. Chem. Eng. J. 2023 , 459 , 141211..

Shi, C.; Quinn, E. C.; Diment, W. T.; Chen, E. Y. X. Recyclable and (bio)degradable polyesters in a circular plastics economy. Chem. Rev. 2024 , 124 , 4393−4478..

Cheng, Y.; Hirano, E.; Wang, H.; Kuwayama, M.; Meijer, E. W.; Huang, H.; Aida, T. Mechanically strong yet metabolizable supramolecular plastics by desalting upon phase separation. Science 2024 , 386 , 875−881..

Abel, B. A.; Snyder, R. L.; Coates, G. W. Chemically recyclable thermoplastics from reversible-deactivation polymerization of cyclic acetals. Science 2021 , 373 , 783−789..

Jackson, A. W.; Reddy Mothe, S.; Chennamaneni, L. R.; van Herk, A.; Thoniyot, P. Unraveling the history and revisiting the synthesis of degradable polystyrene analogues via radical ring-opening copolymerization with cyclic ketene acetals. Materials 2020 , 13 , 2325..

Tardy, A.; Honoré, J. C.; Tran, J.; Siri, D.; Delplace, V.; Bataille, I.; Letourneur, D.; Perrier, J.; Nicoletti, C.; Maresca, M.; Lefay, C.; Gigmes, D.; Nicolas, J.; Guillaneuf, Y. Radical copolymerization of vinyl ethers and cyclic ketene acetals as a v ersatile platform to design functional polyesters. Angew. Chem. Int. Ed. 2017 , 56 , 16515−16520..

Zhang, Q.; Qu, D.; Feringa, B. L.; Tian, H. Disulfide-mediated reversible polymerization toward intrinsically dynamic smart materials. J. Am. Chem. Soc. 2022 , 144 , 2022−2033..

Zhang, Q.; Deng, Y.; Shi, C.; Feringa, B. L.; Tian, H.; Qu, D. Dual closed-loop chemical recycling of synthetic polymers by intrinsically reconfigurable poly(disulfides). Matter 2021 , 4 , 1352−1364..

Lee, D.; Wang, H.; Jiang, S.; Verduzco, R. Versatile light-mediated synthesis of degradable bottlebrush polymers using α -lipoic acid. Angew. Chem. Int. Ed . 2024, e202409323..

Deng, Y.; Huang, Z.; Feringa, B. L.; Tian, H.; Zhang, Q.; Qu, D. Converting inorganic sulfur into degradable thermoplastics and adhesives by copolymerization with cyclic disulfides. Nat. Commun. 2024 , 15 , 3855..

Levkovskyi, I. O.; Mochizuki, S.; Zheng, A.; Zhang, X.; Zhang, F. Lipoic acid-b ased poly(disulfide)s: synthesis and biomedical applications. Nano TransMed 2023 , 2 , 100006..

Zhang, Q.; Deng, Y.; Luo, H.; Shi, C.; Geise, G. M.; Feringa, B. L.; Tian, H.; Qu, D. Assembling a natural small molecule into a supramolecular network with high structural order and dynamic functions. J. Am. Chem. Soc. 2019 , 141 , 12804−12814..

Dikshit, K. V.; Visal, A. M.; Janssen, F.; Larsen, A.; Bruns, C. J. Pressure-sensitive supramolecular adhesives based on lipoic acid and biofriendly dynamic cyclodextrin and polyrotaxane cross-linkers. ACS Appl. Mater. Interfaces 2023 , 15 , 17256−17267..

Raeisi, M.; Tsarevsky, N. V. Radical ring-opening polymerization of lipoates: kinetic and thermodynamic aspects. J. Polym. Sci. 2021 , 59 , 675−684..

Zhang, Q.; Shi, C.; Qu, D.; Long, Y.; Feringa, B. L.; Tian, H. Exploring a naturally tailored small molecule for stretchable, self-healing, and adhesive supramolecular polymers. Sci. Adv. 2018 , 4 , eaat8192..

Chen, C.; Yang, X.; Li, S.; Zhang, C.; Ma, Y.; Ma, Y.; Gao, P.; Gao, S.; Huang, X. Tannic acid–thioctic acid hydrogel: a novel injectable supramolecular adhesive gel for wound healing. Green Chem. 2021 , 23 , 1794−1804..

Chen, J.; Guo, D.; Liang, S.; Liu, Z. A supramolecular copolymer based on small molecules, used for a multifunctional adhesive and rapid hemostasis. Polym. Chem. 2020 , 11 , 6670−6680..

Albanese, K. R.; Okayama, Y.; Morris, P. T.; Gerst, M.; Gupta, R.; Speros, J. C.; Hawker, C. J.; Choi, C.; de Alaniz, J. R.; Bates, C. M. Building tunable degradation into high-performance poly(acrylate) pressure-sensitive adhesives. ACS Macro Lett. 2023 , 12 , 787−793..

Albanese, K. R.; Morris, P. T.; Read de Alaniz, J.; Bates, C. M.; Hawker, C. J. Controlled-radical polymerization of α -lipoic acid: a general route to degradable vinyl copolymers. J. Am. Chem. Soc. 2023 , 145 , 22728−22734..

Pal, S.; Shin, J.; DeFrates, K.; Arslan, M.; Dale, K.; Chen, H.; Ramirez, D.; Messersmith, P. B. Recyclable surgical, consumer, and industrial adhesives of poly( a -lipoic acid). Science 2024 , 385 , 877−883..

Wang, Y.; Sun, S.; Wu, P. Adaptive ionogel paint from room-temperature autonomous polymerization of α -thioctic acid for stretchable and healable electronics. Adv. Funct. Mater. 2021 , 31 , 2101494..

Deng, Y.; Zhang, Q.; Shi, C.; Toyoda, R.; Qu, D.; Tian, H.; Feringa, B. L. Acylhydrazine-based reticular hydrogen bonds enable robust, tough, and dynamic supramolecular materials. Sci. Adv. 2022 , 8 , eabk3286..

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