Abstract
The development of degradable and recyclable polymers is an attractive strategy to tackle the post-consumption pollution issue of commercial plastics. Cyclic-acyclic monomers metathesis polymerization (CAMMP) has been recently reported to produce degradable thermoset, thermoplastic and elastomeric polymers, and their degradability is enabled with addition of various chemicals. In this contribution, we demonstrate that the utilization of diene comonomers containing photodegradable moiety can give access to thermoset and thermoplastic materials bearing photo-degradation capabilities The copolymerization of a series easily accessible diene comonomers bearing photodegradable ortho-nitrobenzyl moieties with dicyclopentadiene (DCPD) or cyclooctene (COE) leads to the formation of photodegradable pDCPD thermosets and pCOE thermoplastic polymers with mechanical properties comparable to their non-degradable counterparts. Most importantly, their photo-degradation properties can be efficiently tuned with the addition of ultraviolet absorber during in-situ polymerization.
References
Borrelle SB, Ringma J, Law KL, Monnahan CC, Lebreton L, McGivern A, Murphy E, Jambeck J, Leonard GH, Hilleary MA, Eriksen M, Possingham HP, De Frond H, Gerber LR, Polidoro B, Tahir A, Bernard M, Mallos N, Barnes M, Rochman CM. Science, 2020, 369: 1515–1518
Stürzel M, Mihan S, Mülhaupt R. Chem Rev, 2016, 116: 1398–1433
Sun H, Kabb CP, Sims MB, Sumerlin BS. Prog Polym Sci, 2019, 89: 61–75
Geyer R, Jambeck JR, Law KL. Sci Adv, 2017, 3: e1700782
Mu H, Zhou G, Hu X, Jian Z. Coord Chem Rev, 2021, 435: 213802
MacLeod M, Arp HPH, Tekman MB, Jahnke A. Science, 2021, 373: 61–65
Law KL, Narayan R. Nat Rev Mater, 2022, 7: 104–116
Adili A, Korpusik AB, Seidel D, Sumerlin BS. Angew Chem Int Ed, 2022, 61: e202209085
Garrison JB, Hughes RW, Sumerlin BS. ACS Macro Lett, 2022, 11: 441–446
Garrison JB, Hughes RW, Young JB, Sumerlin BS. Polym Chem, 2022, 13: 982–988
Abel BA, Snyder RL, Coates GW. Science, 2021, 373: 783–789
Jehanno C, Alty JW, Roosen M, De Meester S, Dove AP, Chen EYX, Leibfarth FA, Sardon H. Nature, 2022, 603: 803–814
Yan YT, Wu G, Chen SC, Wang YZ. Sci China Chem, 2022, 65: 943–953
Häußler M, Eck M, Rothauer D, Mecking S. Nature, 2021, 590: 423–427
Eck M, Schwab ST, Nelson TF, Wurst K, Iberl S, Schleheck D, Link C, Battagliarin G, Mecking S. Angew Chem Int Ed, 2023, 62: e202213438
Li C, Guo C, Fitzpatrick V, Ibrahim A, Zwierstra MJ, Hanna P, Lechtig A, Nazarian A, Lin SJ, Kaplan DL. Nat Rev Mater, 2020, 5: 61–81
Tang X, Westlie AH, Caporaso L, Cavallo L, Falivene L, Chen EY. Angew Chem Int Ed, 2020, 59: 7881–7890
Clarke RW, Sandmeier T, Franklin KA, Reich D, Zhang X, Vengallur N, Patra TK, Tannenbaum RJ, Adhikari S, Kumar SK, Rovis T, Chen EYX. Nature, 2023, 616: 731–739
Shieh P, Zhang W, Husted KEL, Kristufek SL, Xiong B, Lundberg DJ, Lem J, Veysset D, Sun Y, Nelson KA, Plata DL, Johnson JA. Nature, 2020, 583: 542–547
Liu Z, Fang Z, Zheng N, Yang K, Sun Z, Li S, Li W, Wu J, Xie T. Nat Chem, 2023, 15: 1773–1779
Xiong W, Lu H. Sci China Chem, 2023, 66: 725–738
Bhatkhande DS, Pangarkar VG, Beenackers AACM. J Chem Tech Biotech, 2002, 77: 102–116
Feng X, Yu Z, Sun Y, Long R, Shan M, Li X, Liu Y, Liu J. Ceramics Int, 2021, 47: 7321–7343
Nasir AM, Awang N, Jaafar J, Ismail AF, Othman MHD, A. Rahman M, Aziz F, Mat Yajid MA. J Water Process Eng, 2021, 40: 101878
Zhang M, Yang Y, An X, Hou L. Chem Eng J, 2021, 412: 128663
Oh XY, Nguyen TM, Ye E, Luo HK, Singh PND, Loh XJ, Truong VX. ACS Macro Lett, 2023, 12: 690–696
Koo B, Kim D, Song DY, Han WJ, Kim D, Park JW, Kim M, Kim C. Polym Chem, 2022, 13: 6268–6273
Yuan P, Sun Y, Xu X, Luo Y, Hong M. Nat Chem, 2022, 14: 294–303
Zhang X, Guo W, Zhang C, Zhang X. Nat Commun, 2023, 14: 5423
Huang HY, Xiong W, Huang YT, Li K, Cai Z, Zhu JB. Nat Catal, 2023, 6: 720–728
Liu J, Ren W, Lu X. Sci China Chem, 2015, 58: 999–1004
Li XL, Clarke RW, Jiang JY, Xu TQ, Chen EYX. Nat Chem, 2023, 15: 278–285
Lidston CAL, Abel BA, Coates GW. J Am Chem Soc, 2020, 142: 20161–20169
Eck M, Bernabeu L, Mecking S. ACS Sustain Chem Eng, 2023, 11: 4523–4530
Arrington AS, Brown JR, Win MS, Winey KI, Long TE. Polym Chem, 2022, 13: 3116–3125
Si G, Tan C, Chen M, Chen C. Angew Chem Int Ed, 2022, 61: e202203796
Parke SM, Lopez JC, Cui S, LaPointe AM, Coates GW. Angew Chem Int Ed, 2023, 62: e202301927
Kocen AL, Cui S, Lin TW, LaPointe AM, Coates GW. J Am Chem Soc, 2022, 144: 12613–12618
Pearce AK, Foster JC, O’Reilly RK. J Polym Sci PartA-Polym Chem, 2019, 57: 1621–1634
Neary WJ, Isais TA, Kennemur JG. J Am Chem Soc, 2019, 141: 14220–14229
Bachmann J, Petit C, Michalek L, Catel Y, Blasco E, Blinco JP, Unterreiner AN, Barner-Kowollik C. ACS Macro Lett, 2021, 10: 447–452
Bai J, Wang Y, You W. Sci China Chem, 2022, 65: 2182–2187
Feist JD, Lee DC, Xia Y. Nat Chem, 2022, 14: 53–58
Feist JD, Xia Y. J Am Chem Soc, 2020, 142: 1186–1189
Elling BR, Su JK, Xia Y. ACS Macro Lett, 2020, 9: 180–184
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
Zhou J, Sathe D, Wang J. J Am Chem Soc, 2022, 144: 928–934
Sample CS, Kellstedt EA, Hillmyer MA. ACS Macro Lett, 2022, 11: 608–614
Shieh P, Nguyen HVT, Johnson JA. Nat Chem, 2019, 11: 1124–1132
Husted KEL, Shieh P, Lundberg DJ, Kristufek SL, Johnson JA. ACS Macro Lett, 2021, 10: 805–810
Si G, Chen C. Nat Synth, 2022, 1: 956–966
Deng X, Zheng N, Song Z, Yin L, Cheng J. Biomaterials, 2014, 35: 5006–5015
Wang Q, Min Z, Wong YD, Li M, Huang W. JAppl Polym Sci, 2023, 140: e53913
Liu L, Liu L, Liu Z, Yang C, Pan B, Li W. Materials, 2022, 15: 8110
Acknowledgements
This work was supported by the National Key R&D Program of China (2021YFA1501700), the National Natural Science Foundation of China (52025031, 22261142664, 22301294), China Postdoctoral Science Foundation (BX20230339, 2023M743352), the CAS Project for Young Scientists in Basic Research (YSBR-094), and Anhui Province Key Research and Development Plan Project (2022j11020004).
Author information
Authors and Affiliations
Corresponding authors
Ethics declarations
Conflict of interest The authors declare no conflict of interest.
Additional information
Supporting information The supporting information is available online at http://chem.scichina.com and http://link.springer.com/journal/11426. The supporting materials are published as submitted, without typesetting or editing. The responsibility for scientific accuracy and content remains entirely with the authors.
Rights and permissions
About this article
Cite this article
Li, W., Liao, D., Li, Y. et al. Cyclic-acyclic monomers metathesis polymerization to access photodegradable polydicyclopentadiene and polyethylene-like materials. Sci. China Chem. 67, 1311–1315 (2024). https://doi.org/10.1007/s11426-023-1883-4
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11426-023-1883-4