Well-controlled Organocatalytic Ring-opening Polymerization of Seven-membered Cyclic Carbonates with Cyclohexyl Fusion

doi:10.1007/s40242-024-4094-5

Abstract

Abstract: Developing green and well-controlled polymerization methods is of great significance for the preparation of biomedical polymer materials. In this contribution, an efficient organocatalytic ring-opening polymerization (ROP) of a class of seven-membered cyclic carbonates (T6DO, T6HDO, C6DO, C6HDO) containing cis- or trans-cyclohexane structure was established. Organic catalyst 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) promoted living polymerization of these cyclic carbonates to deliver polycarbonate and block copolymer products with predictable molecular weights and narrow dispersity. The robust TBD-mediated ROP at 90 ℃ showcased turnover frequency (TOF) up to 10³ h^-1. The resulting amorphous polycarbonates displayed good thermal stability.

Key words: CO₂, Organic catalyst, Living ring-opening polymerization, Aliphatic polycarbonate

ZHANG Wei, SHAN Si-Yi, DAI Jiang, CAI Zhongzheng, ZHU Jian-Bo. Well-controlled Organocatalytic Ring-opening Polymerization of Seven-membered Cyclic Carbonates with Cyclohexyl Fusion[J]. Chemical Research in Chinese Universities, 2024, 40(5): 856-862.

References

[1] Zhang X., Zhao B. W., Fu S. W., Seruya R. S., Madey J. F., III, Bukhryakova E., Zhang F. W., Macromolecules, 2024, 57, 2858.
[2] Wu R., Gilavan M. T., Akbar M. A., Fan L., Selvaganapathy P. R., Carbon, 2024, 216, 118597.
[3] Wei P. R., Bhat G. A., Darensbourg D. J., Angew. Chem. Int. Ed., 2023, 135, e202307507.
[4] Chen C. X., Hou Z. P., Chen S. W., Guo J., Chen Z. P., Hu J. S., Yang L. Q., Compos Part B: Eng., 2022, 240, 109985.
[5] Shen Y. D., Leng M. W., Yang Y. C., Boopathi S. K., Sun G. R., Wooley K. L., J. Am. Chem. Soc., 2023, 145, 15405.
[6] Sundermann D. A., Park B., Hirschberg V., Schaefer J. L., Théato P., ACS Omega, 2023, 8, 23510.
[7] Sun W., Lu K. Y., Wang L., Hao Q., Liu J. R., Wang Y., Wu Z. Q., Chen H., J. Mater. Chem. B, 2022, 10, 5203.
[8] Watanabe Y., Takaoka S., Haga Y., Kishi K., Hakozaki S., Narumi A., Kato T., Tanaka M., Fukushima K., Polym. Chem., 2022, 13, 5193.
[9] Yu W., Maynard E., Chiaradia V., Arno M. C., Dove A. P., Chem. Rev., 2021, 121, 10865.
[10] Chanthaset N., Beckerle K., Okuda J., Ajiro H., J. Appl. Polym. Sci., 2020, 137, 49073.
[11] Li M., Behzadi S., Chen M., Pang W. M., Wang F. Z., Tan C., Organometallics, 2019, 38, 461.
[12] Okamoto H., Sogabe A., Honda S., Commun. Chem., 2024, 7, 61.
[13] Li Z. D., Duan S. W., Zhao N., Li Z. B., J. Polym. Sci., 2023, 61, 1688.
[14] Zaky M. S., Wirotius A.-L., Coulembier O., Guichard G., Taton D., ACS Macro Lett., 2022, 11, 1148.
[15] Ungpittagul T., Virachotikul A., Monot J., Martín-Vaca B., Bourissou D., Adv. Synth. Catal., 2024, 366, 733.
[16] McMichael P., Schultze X., Cramail H., Peruch F., Eur. Polym. J., 2024, 208, 112859.
[17] Sardon H., Macromolecules, 2022, 55, 3769.
[18] Dove A. P., ACS Macro Lett., 2012, 1, 1409.
[19] Dai J., Xiong W., Li D.-Y., Cai Z., Zhu J.-B., Chem. Commun., 2023, 59, 12731.
[20] Liu Y. X., Zhang J. B., Kou X. H., Liu S. F., Li Z. B., ACS Macro Lett., 2022, 11, 1183.
[21] Jiang X., Zhao N., Li Z. B., Chin. J. Chem., 2021, 39, 2403.
[22] Zhu J.-B., Chen E. Y. X., J. Am. Chem. Soc., 2015, 137, 12506.
[23] Orhan B., Tschan M. J. L., Wirotius A.-L., Dove A. P., Coulembier O., Taton D., ACS Macro Lett., 2018, 7, 1413.
[24] Lv C. D., Zhou L., Yuan R. T., Mahmood Q., Xu G. Q., Wang Q. G., New J. Chem., 2020, 44, 1648.
[25] Li Z. Y., Qian Y. L., Lai Y. H., Du F.-S., Li Z.-C., Biomacromolecules, 2022, 23, 5213.
[26] Lin B. H., Waymouth R. M., Macromolecules, 2018, 51, 2932.
[27] Lv C. D., Yang R. L., Xu G. Q., Zhou L., Wang Q. G., Eur. Polym. J., 2020, 133, 109792.
[28] Wang X.-M., Huang H.-Y., Tu Y.-M., Cai Z., Zhu J.-B., Polym. Chem., 2023, 14, 2027.
[29] Wang M. Q., Ding Z. Q., Shi X. C., Ma Z., Wang B., Li Y. S., Macromolecules, 2024, 57, 869.
[30] Dai J., Xiong W., Du M.-R., Wu G., Cai Z., Zhu J.-B., Sci. China Chem., 2022, 66, 251.
[31] Stellmach K. A., Paul M. K., Xu M. Z., Su Y. L., Fu L. B., Toland A. R., Tran H., Chen L. H., Ramprasad R., Gutekunst W. R., ACS Macro Lett., 2022, 11, 895.
[32] Xia Y. L., Yuan P. J., Zhang Y. P., Sun Y. Y., Hong M., Angew. Chem. Int. Ed., 2023, 62, e202217812.
[33] Wang Y. C., Zhu Y. N., Lv W. X., Wang X. H., Tao Y. H., J. Am. Chem. Soc., 2023, 145, 1877.
[34] Yuan J. S., Xiong W., Zhou X. H., Zhang Y., Shi D., Li Z. C., Lu H., J. Am. Chem. Soc., 2019, 141, 4928.
[35] Xiong W., Chang W. Y., Shi D., Yang L. J., Tian Z. Y., Wang H., Zhang Z. C., Zhou X. H., Chen E.-Q., Lu H., Chem, 2020, 6, 1831.
[36] Shen Y. D., Yang X., Song Y., Tran D. K., Wang H., Wilson J., Dong M., Vazquez M., Sun G. R., Wooley K. L., JACS Au, 2022, 2, 515.
[37] Lamparelli D. H., Villar-Yanez A., Dittrich L., Rintjema J., Bravo F., Bo C., Kleij A. W., Angew. Chem., 2023, 135, e202314659.
[38] Makiguchi K., Ogasawara Y., Kikuchi S., Satoh T., Kakuchi T., Macromolecules, 2013, 46, 1772.
[39] Fukushima K., Honda K., Inoue Y., Tanaka M., Eur. Polym. J., 2017, 95, 728.
[40] Fukushima K., Nozaki K., Macromolecules, 2020, 53, 5018.
[41] Venkataraman S., Ng V. W. L., Coady D. J., Horn H. W., Jones G. O., Fung T. S., Sardon H., Waymouth R. M., Hedrick J. L., Yang Y. Y., J. Am. Chem. Soc., 2015, 137, 13851.
[42] Helou M., Miserque O., Brusson J. M., Carpentier J. F., Guillaume S. M., Chem.-Eur. J., 2010, 16, 13805.
[43] Siragusa F., Van Den Broeck E., Ocando C., Müller A. J., De Smet G., Maes B. U. W., De Winter J., Van Speybroeck V., Grignard B., Detrembleur C., ACS Sustain. Chem. Eng., 2021, 9, 1714.
[44] Shan S.-Y., Zhang W., Cao Q., Ye Y.-C., Cai Z., Zhu J.-B., Polym. Chem., 2024, 15, 1070.
[45] Zhang W., Dai J., Wu Y.-C., Chen J.-X., Shan S.-Y., Cai Z., Zhu J.-B., ACS Macro Lett., 2022, 11, 173.
[46] Wu Y.-C., Fan H.-Z., Zhang W., Wang M.-Y., Cai Z., Zhu J.-B., Macromolecules, 2022, 55, 9232.
[47] Wu Y.-C., Fan H.-Z., Shan S.-Y., Wang S.-Q., Cai Z., Zhu J.-B., Chem. Res. Chinese Universities, 2023, 39, 809.
[48] Yang X., Zhang W., Huang H.-Y., Dai J., Wang M.-Y., Fan H.-Z., Cai Z., Zhang Q., Zhu J.-B., Macromolecules, 2022, 55, 2777.