Abstract
Developing new chemically recyclable polymers is important for a circular plastics economy. Herein, we prepared a class of 1,4-dithian-2-one (DTO) with thioether and thioester functionalities. These sulfur-substituted monomers (DTO) showed excellent reactivity for ring-opening polymerization (turnover frequency (TOF) up to 2.3 × 104h−1), which afforded poly(thioether-thioester)s (P(DTO)s) with high air stability, high crystallinity, and commercial high-density polyethylene-like mechanical property (σB = 29.59 ± 1.08 MPa and εB = 749% ± 36%). Intriguingly, chemical recycling of P(DTO) to monomer could be accomplished with excellent efficiency in dilute solution (1 min) at room temperature or even from a commodity plastic waste mixture under catalyst-free thermal bulk condition (180 °C), thus establishing its circular life cycle. P(Me-DTO) could be applied for selective removal of Hg2+ with >99% removal efficiency. More importantly, Me-DTO could be recovered in high yield after utilization for Hg2+ adsorption.
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References
Law KL, Narayan R. Nat Rev Mater, 2022, 7: 104–116
Cywar RM, Rorrer NA, Hoyt CB, Beckham GT, Chen EYX. Nat Rev Mater, 2022, 7: 83–103
Zhu Y, Romain C, Williams CK. Nature, 2016, 540: 354–362
Hong M, Chen EYX. Green Chem, 2017, 19: 3692–3706
Coates GW, Getzler YDYL. Nat Rev Mater, 2020, 5: 501–516
Xu G, Wang Q. Green Chem, 2022, 24: 2321–2346
Lu XB, Liu Y, Zhou H. Chem Eur J, 2018, 24: 11255–11266
Hong M, Chen EYX. Nat Chem, 2016, 8: 42–49
Zhu JB, Watson EM, Tang J, Chen EYX. Science, 2018, 360: 398–403
Abel BA, Snyder RL, Coates GW. Science, 2021, 373: 783–789
Singer FN, Deacy AC, McGuire TM, Williams CK, Buchard A. Angew Chem Int Ed, 2022, 61: e202201785
MacDonald JP, Shaver MP. Polym Chem, 2016, 7: 553–559
Li C, Wang L, Yan Q, Liu F, Shen Y, Li Z. Angew Chem Int Ed, 2022, 61: e202201407
Nishida H, Yamashita M, Hattori N, Endo T, Tokiwa Y. Polym Degrad Stab, 2000, 70: 485–496
Shi CX, Guo YT, Wu YH, Li ZY, Wang YZ, Du FS, Li ZC. Macromolecules, 2019, 52: 4260–4269
Li LG, Wang QY, Zheng QY, Du FS, Li ZC. Macromolecules, 2021, 54: 6745–6752
Tu YM, Wang XM, Yang X, Fan HZ, Gong FL, Cai Z, Zhu JB. J Am Chem Soc, 2021, 143: 20591–20597
Fan HZ, Yang X, Chen JH, Tu YM, Cai Z, Zhu JB. Angew Chem Int Ed, 2022, 61: e202117639
Zhang W, Dai J, Wu YC, Chen JX, Shan SY, Cai Z, Zhu JB. ACS Macro Lett, 2022, 11: 173–178
Sathe D, Zhou J, Chen H, Su HW, Xie W, Hsu TG, Schrage BR, Smith T, Ziegler CJ, Wang J. Nat Chem, 2021, 13: 743–750
Liu Y, Zhou H, Guo JZ, Ren WM, Lu XB. Angew Chem Int Ed, 2017, 56: 4862–4866
Olsén P, Odelius K, Albertsson AC. Macromolecules, 2014, 47: 6189–6195
Zhang Q, Deng Y, Shi CY, Feringa BL, Tian H, Qu DH. Matter, 2021, 4: 1352–1364
Li J, Liu F, Liu Y, Shen Y, Li Z. Angew Chem Int Ed, 2022, 61: e202207105
Yan YT, Wu G, Chen SC, Wang YZ. Sci China Chem, 2022, 65: 943–953
Yu Y, Gao B, Liu Y, Lu XB. Angew Chem Int Ed, 2022, 61: e202204492
Lim J, Pyun J, Char K. Angew Chem Int Ed, 2015, 54: 3249–3258
Mutlu H, Ceper EB, Li X, Yang J, Dong W, Ozmen MM, Theato P. Macromol Rapid Commun, 2019, 40: 1800650
Hasell T, Parker DJ, Jones HA, McAllister T, Howdle SM. Chem Commun, 2016, 52: 5383–5386
Cao W, Dai F, Hu R, Tang BZ. J Am Chem Soc, 2020, 142: 978–986
Chung WJ, Griebel JJ, Kim ET, Yoon H, Simmonds AG, Ji HJ, Dirlam PT, Glass RS, Wie JJ, Nguyen NA, Guralnick BW, Park J, Somogyi A, Theato P, Mackay ME, Sung YE, Char K, Pyun J. Nat Chem, 2013, 5: 518–524
Zhang CJ, Zhu TC, Cao XH, Hong X, Zhang XH. J Am Chem Soc, 2019, 141: 5490–5496
Suzuki M, Makimura K, Matsuoka S. Biomacromolecules, 2016, 17: 1135–1141
Yue TJ, Zhang MC, Gu GG, Wang LY, Ren WM, Lu XB. Angew Chem Int Ed, 2019, 58: 618–623
Yuan P, Sun Y, Xu X, Luo Y, Hong M. Nat Chem, 2022, 14: 294–303
Yang X, Zhang W, Huang HY, Dai J, Wang MY, Fan HZ, Cai Z, Zhang Q, Zhu JB. Macromolecules, 2022, 55: 2777–2786
Yuan J, Xiong W, Zhou X, Zhang Y, Shi D, Li Z, Lu H. J Am Chem Soc, 2019, 141: 4928–4935
Shi C, McGraw ML, Li ZC, Cavallo L, Falivene L, Chen EYX. Sci Adv, 2020, 6: eabc0495
Xiong W, Chang W, Shi D, Yang L, Tian Z, Wang H, Zhang Z, Zhou X, Chen EQ, Lu H. Chem, 2020, 6: 1831–1843
Wang Y, Li M, Chen J, Tao Y, Wang X. Angew Chem Int Ed, 2021, 60: 22547–22553
Yang KK, Wang XL, Wang YZ. J MacroMol Sci Part C-Polym Rev, 2002, 42: 373–398
Tian GQ, Yang ZH, Zhang W, Chen SC, Chen L, Wu G, Wang YZ. Green Chem, 2022, 24: 4490–4497
Liu ZP, Ding SD, Sui YJ, Wang YZ. J Appl Polym Sci, 2009, 112: 3079–3086
Stellmach KA, Paul MKK, Xu M, Su YL, Fu L, Toland AR, Tran H, Chen L, Ramprasad R, Gutekunst WR. ACS Macro Lett, 2022, 11: 895–901
Larsen J, Lenoir C. Synthesis, 1989, 1989: 134
Yang ZH, Tian GQ, Chen SC, Wu G. Acta Polym Sin, 2022, 53: 236–244
Li L, Chen X, Xia Q, Wei X, Liu J, Fan Z, Guo M. Carbohydr Polym, 2016, 142: 82–90
Sperling L. Mechanical behavior of polymers. In: Sperling LH, Ed. Introduction to Physical Polymer Science. 4th Ed. Chapter 11. Hoboken: John Wiley & Sons, Inc., 2005. 557–612
Lipinski BM, Morris LS, Silberstein MN, Coates GW. J Am Chem Soc, 2020, 142: 6800–6806
Rapagnani RM, Dunscomb RJ, Fresh AA, Tonks IA. Nat Chem, 2022, 14: 877–883
Acknowledgements
This work was supported by the National Key R&D Program of China (2021YFA1501700), the National Natural Science Foundation of China (51903177, U19A2095), the “1000-Youth Talents Program”, and the Fundamental Research Funds for the Central Universities (YJ201924, YJ202209). We would like to thank Dr. Dongyan Deng from the College of Chemistry, Sichuan University for NMR testing and Dr. Xi Wu from the analytic testing center, Sichuan University for AAS testing.
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Dai, J., Xiong, W., Du, MR. et al. A facile approach towards high-performance poly(thioether-thioester)s with full recyclability. Sci. China Chem. 66, 251–258 (2023). https://doi.org/10.1007/s11426-022-1392-8
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DOI: https://doi.org/10.1007/s11426-022-1392-8