从<italic style="font-style: italic">O</italic>-羧基环内酸酐的开环聚合到阴离子结合催化聚合方法的发现

李茂盛; 陶友华

doi:10.11777/j.issn1000-3304.2024.24271

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从O-羧基环内酸酐的开环聚合到阴离子结合催化聚合方法的发现

专论 | 更新时间：2025-02-27

- 从O-羧基环内酸酐的开环聚合到阴离子结合催化聚合方法的发现
- From Ring-opening Polymerization of O-carboxyanhydride to the Discovery of Anion-binding Catalytic Polymerization
- 高分子学报 2025年56卷第3期页码：361-376
- 作者机构：
  
  中国科学院长春应用化学研究所中国科学院生态环境高分子材料重点实验室长春 130022
- 作者简介：
  
  [ "李茂盛，男，1990年生‍. 中国科学院长春应用化学研究所副研究员‍. 2012年本科毕业于吉林大学化学学院；2020年于中国科学院长春应用化学研究所高分子化学与物理专业获博士学位，导师为陶友华研究员‍. 荣获2021年度中国科学院优秀博士学位论文，并入选2023年度中国科学院青年创新促进会会员‍. 主持了国家自然科学基金青年科学基金和面上项目、吉林省科技厅国际科技合作项目等‍. 主要研究方向为非共价催化聚合‍." ]
  [ "陶友华，男，1981年生. 中国科学院长春应用化学研究所研究员，博士生导师. 获得国家杰出青年科学基金资助. 2008年在长春应化所获理学博士学位；随后在日本名古屋大学以及美国科罗拉多大学博尔德分校作博士后研究‍. 2013年回到中国科学院长春应用化学研究所，并入选中科院高层次人才计划. 主要从事非共价催化的氨基酸高分子合成研究，在生物基尼龙及闭环回收的聚硫酯的制备、性能研究方面也有很好的积累‍. 以通讯作者在Nat. Synth.、J. Am. Chem. Soc.、Angew. Chem. Int. Ed.等杂志发表论文五十余篇，发明的七元环状赖氨酸单体正在与中石化合作推进工业化. 获2023年度“中国化学会高分子科学邀请报告荣誉奖”，并在2023年全国高分子学术论文报告会作大会报告. 现任中国化学会应用化学学科委员会秘书长，《高分子学报》等期刊编委." ]
- 基金信息：
  
  国家重点研发计划(基金号 2022YFE0130500);国家自然科学基金(基金号 ┣22001243);22371274┫;中国科学院国际伙伴计划(基金号 121522KYSB20210045)
- DOI：10.11777/j.issn1000-3304.2024.24271
  中图分类号：
- CSTR：32057.14.GFZXB.2024.7335
- 收稿日期：2024-11-04，
  
  录用日期：2024-12-19，
  
  网络出版日期：2025-01-23，
  
  纸质出版日期：2025-03-20
- 稿件说明：
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李茂盛, 陶友华. 从O-羧基环内酸酐的开环聚合到阴离子结合催化聚合方法的发现. 高分子学报, 2025, 56(3), 361-376

Li, M. S.; Tao, Y. H. From ring-opening polymerization of O-carboxyanhydride to the discovery of anion-binding catalytic polymerization. Acta Polymerica Sinica, 2025, 56(3), 361-376
李茂盛, 陶友华. 从O-羧基环内酸酐的开环聚合到阴离子结合催化聚合方法的发现. 高分子学报, 2025, 56(3), 361-376 DOI： 10.11777/j.issn1000-3304.2024.24271. CSTR： 32057.14.GFZXB.2024.7335.

Li, M. S.; Tao, Y. H. From ring-opening polymerization of O-carboxyanhydride to the discovery of anion-binding catalytic polymerization. Acta Polymerica Sinica, 2025, 56(3), 361-376 DOI： 10.11777/j.issn1000-3304.2024.24271. CSTR： 32057.14.GFZXB.2024.7335.

摘要

随着全球社会对可持续发展的日益重视，探索高效、绿色、安全及经济的可持续聚合新方法，实现高分子材料的精准合成，已成为高分子合成化学的研究重点. 近年来，我们突破链式聚合主要依赖金属催化剂调控链末端的局限，创新性地提出阴离子结合催化聚合理念，旨在通过氢键给体与阴离子物种之间的非共价相互作用来动态结合、识别与活化链末端，从而实现聚合活性和选择性的统一. 本文首先从

-羧基环内酸酐单体的开环聚合研究出发，综述了该领域的发展脉络和代表性研究进展. 接着，回顾和梳理了我们针对该领域的关键挑战而开展的系列研究工作，重点介绍了阴离子结合催化聚合方法的提出背景与建立过程. 最后，展望了这种新兴催化聚合方法的未来发展趋势. 我们相信，利用非共价相互作用来催化挑战性的离子聚合，代表了一个前景广阔的聚合催化研究新方向，必将在推动高分子科学及其产业的可持续发展中发挥重要作用.

Abstract

With the increasingly emphasizes on sustainable development

exploring efficient

green

safe

and economical new sustainable polymerization methodologies has become a central focus in polymer synthesis. To address the limitations of chain polymerization primarily relying on metal catalysts to regulate chain ends

we have recently developed an innovative concept of anion-binding catalytic polymerization

where the hydrogen bond donors could leverage non-covalent anion-binding interactions to dynamically bind

recognize and activate propagating species

thereby achieving ideal polymerization activity and selectivity. This article begins by reviewing the development and representative research progress in ring-opening p

olymerization (ROP) of

-carboxyanhydrides (OCA). It then revisits and organizes our series of research efforts for addressing key challenges in this area

with a particular focus on the background and establishment of the anion-binding catalytic polymerization method. Finally

we discuss the future development trends of this emerging catalytic polymerization approach. We believe that utilizing non-covalent interactions to catalyze challenging ionic polymerization represents a promising new direction in polymerization catalysis

which will significantly contribute to the sustainable development of polymer science and its associated industries.

关键词

Keywords

references

Staudinger, H. Über polymerisation . Ber. Dtsch. Chem. Ges. A/B , 1920 , 53 ( 6 ), 1073 - 1085 . doi: 10.1002/cber.19200530627 http://dx.doi.org/10.1002/cber.19200530627

安泽胜 , 陈昶乐 , 何军坡 , 洪春雁 , 李志波 , 李子臣 , 刘超 , 吕小兵 , 秦安军 , 曲程科 , 唐本忠 , 陶友华 , 宛新华 , 王国伟 , 王佳 , 郑轲 , 邹文凯 . 中国高分子合成化学的研究与发展动态 . 高分子学报 , 2019 , 50 ( 10 ), 1083 - 1132 . doi: 10.11777/j.issn1000-3304.2019.19136 http://dx.doi.org/10.11777/j.issn1000-3304.2019.19136

陈学思 , 陈国强 , 陶友华 , 王玉忠 , 吕小兵 , 张立群 , 朱锦 , 张军 , 王献红 . 生态环境高分子的研究进展 . 高分子学报 , 2019 , 50 ( 10 ), 1068 - 1082 . doi: 10.11777/j.issn1000-3304.2019.19124 http://dx.doi.org/10.11777/j.issn1000-3304.2019.19124

张留乔 , 黄智豪 , 张正彪 , 朱秀林 . 序列可控高分子的合成及应用 . 高分子学报 , 2018 , ( 9 ), 1144 - 1154 . doi: 10.11777/j.issn1000-3304.2018.18101 http://dx.doi.org/10.11777/j.issn1000-3304.2018.18101

Kato M. ; Kamigaito M. ; Sawamoto M. ; Higashimura T. Polymerization of methyl methacrylate with the carbon tetrachloride/dichlorotris-‍(triphenylphosphine)ruthenium(II)/methylaluminum ‍bis ( 2 ,‍ 6 -di-tert-butylphenoxide) initiating system: possibility of living radical polymerization . Macromolecules, 1995, 28 ( 5 ), 1721 - 1723 . doi: 10.1021/ma00109a056 http://dx.doi.org/10.1021/ma00109a056

Wang J. S. ; Matyjaszewski K. Controlled/"living" radical polymerization. Atom transfer radical polymerization in the presence of transition-metal complexes . J. Am. Chem. Soc. , 1995 , 117 ( 20 ), 5614 - 5615 . doi: 10.1021/ja00125a035 http://dx.doi.org/10.1021/ja00125a035

Grubbs R. H. ; Tumas W. Polymer synthesis and organotransition metal chemistry . Science , 1989 , 243 ( 4893 ), 907 - 915 . doi: 10.1126/science.2645643 http://dx.doi.org/10.1126/science.2645643

Lund H. ; Hanngren Å. ; Theander O. ; Zackrisson M. ; Ernster L. ; Diczfalusy E. Infrared spectra properties of hydrogen bonding systems containing anions . Acta Chem. Scand. , 1958 , 12 , 298 - 302 . doi: 10.3891/acta.chem.scand.12-0298 http://dx.doi.org/10.3891/acta.chem.scand.12-0298

Hedstrom L. Serine protease mechanism and specificity . Chem. Rev. , 2002 , 102 ( 12 ), 4501 - 4524 . doi: 10.1021/cr000033x http://dx.doi.org/10.1021/cr000033x

Dutzler R. ; Campbell E. B. ; Cadene M. ; Chait B. T. ; MacKinnon R. X-ray structure of a ClC chloride channel at 3.0 Å reveals the molecular basis of anion selectivity . Nature , 2002 , 415 ( 6869 ), 287 - 294 . doi: 10.1038/415287a http://dx.doi.org/10.1038/415287a

Dutzler R. ; Campbell E. B. ; MacKinnon R. Gating the selectivity filter in ClC chloride channels . Science , 2003 , 300 ( 5616 ), 108 - 112 . doi: 10.1126/science.1082708 http://dx.doi.org/10.1126/science.1082708

Davis A. P. ; Sheppard D. N. ; Smith B. D. Development of synthetic membrane transporters for anions . Chem. Soc. Rev. , 2007 , 36 ( 2 ), 348 - 357 . doi: 10.1039/b512651g http://dx.doi.org/10.1039/b512651g

Dressler F. ; Schreiner, P. From anion recognition to organocatalytic chemical reactions . In: Anion‐Binding Catalysis , 2022 . 1 - 77 . doi: 10.1002/9783527830664.ch1 http://dx.doi.org/10.1002/9783527830664.ch1

Beer P. D. ; Gale P. A. Anion recognition and sensing: the state of the art and future perspectives . Angew. Chem. Int. Ed. , 2001 , 40 ( 3 ), 486 - 516 . doi: 10.1002/1521-3773(20010202)40:3<486::aid-anie486>3.0.co;2-p http://dx.doi.org/10.1002/1521-3773(20010202)40:3<486::aid-anie486>3.0.co;2-p

Caltagirone C. ; Gale P. A. Anion receptor chemistry: highlights from 2007 . Chem. Soc. Rev. , 2009 , 38 ( 2 ), 520 - 563 . doi: 10.1039/b806422a http://dx.doi.org/10.1039/b806422a

Gale P. A. ; Busschaert N. ; Haynes C. J. E. ; Karagiannidis L. E. ; Kirby I. L. Anion receptor chemistry: highlights from 2011 and 2012 . Chem. Soc. Rev. , 2014 , 43 ( 1 ), 205 - 241 . doi: 10.1039/c3cs60316d http://dx.doi.org/10.1039/c3cs60316d

Busschaert N. ; Caltagirone C. ; van Rossom W. ; Gale P. A. Applications of supramolecular anion recognition . Chem. Rev. , 2015 , 115 ( 15 ), 8038 - 8155 . doi: 10.1021/acs.chemrev.5b00099 http://dx.doi.org/10.1021/acs.chemrev.5b00099

Chen L. J. ; Berry S. N. ; Wu X. ; Howe E. N. W. ; Gale P. A. Advances in anion receptor chemistry . Chem , 2020 , 6 ( 1 ), 61 - 141 . doi: 10.1016/j.chempr.2019.12.002 http://dx.doi.org/10.1016/j.chempr.2019.12.002

McNaughton D. A. ; Ryder W. G. ; Gilchrist A. M. ; Wang P. ; Fares M. ; Wu X. ; Gale P. A. New insights and discoveries in anion receptor chemistry . Chem , 2023 , 9 ( 11 ), 3045 - 3112 . doi: 10.1016/j.chempr.2023.07.006 http://dx.doi.org/10.1016/j.chempr.2023.07.006

Wang Q. Q. Anion recognition-directed supramolecular catalysis with functional macrocycles and molecular cages . Acc. Chem. Res. , 2024 , 57 ( 21 ), 3227 - 3240 . doi: 10.1021/acs.accounts.4c00583 http://dx.doi.org/10.1021/acs.accounts.4c00583

Mahlau M. ; List B. Asymmetric counteranion-directed catalysis: concept, definition, and applications . Angew. Chem. Int. Ed. , 2013 , 52 ( 2 ), 518 - 533 . doi: 10.1002/anie.201205343 http://dx.doi.org/10.1002/anie.201205343

Brak K. ; Jacobsen E. N. Asymmetric ion-pairing catalysis . Angew. Chem. Int. Ed. , 2013 , 52 ( 2 ), 534 - 561 . doi: 10.1002/anie.201205449 http://dx.doi.org/10.1002/anie.201205449

Zhang, Z. G.; Schreiner, P. R. (Thio)urea organocatalysis: what can be learnt from anion recognition? Chem. Soc. Rev. , 2009 , 38 ( 4 ), 1187 - 1198 . doi: 10.1039/b801793j http://dx.doi.org/10.1039/b801793j

Knowles R. R. ; Jacobsen E. N. Attractive noncovalent interactions in asymmetric catalysis: links between enzymes and small molecule catalysts . Proc. Natl. Acad. Sci. USA , 2010 , 107 ( 48 ), 20678 - 20685 . doi: 10.1073/pnas.1006402107 http://dx.doi.org/10.1073/pnas.1006402107

Phipps R. J. ; Hamilton G. L. ; Toste F. D. The progression of chiral anions from concepts to applications in asymmetric catalysis . Nat. Chem. , 2012 , 4 , 603 - 614 . doi: 10.1038/nchem.1405 http://dx.doi.org/10.1038/nchem.1405

Neel A. J. ; Hilton M. J. ; Sigman M. S. ; Toste F. D. Exploiting non-covalent π interactions for catalyst design . Nature , 2017 , 543 ( 7647 ), 637 - 646 . doi: 10.1038/nature21701 http://dx.doi.org/10.1038/nature21701

Macheño O. G. , ed. , Anion-Binding Catalysis , Wiley-VCH GmbH . 2022

Olivo G. ; Capocasa G. ; Del Giudice D. ; Lanzalunga O. ; Di Stefano S. New horizons for catalysis disclosed by supramolecular chemistry . Chem. Soc. Rev. , 2021 , 50 ( 13 ), 7681 - 7724 . doi: 10.1039/d1cs00175b http://dx.doi.org/10.1039/d1cs00175b

Min C. ; Seidel D. Asymmetric Brønsted acid catalysis with chiral carboxylic acids . Chem. Soc. Rev. , 2017 , 46 ( 19 ), 5889 - 5902 . doi: 10.1039/c6cs00239k http://dx.doi.org/10.1039/c6cs00239k

Kiesewetter M. K. ; Shin E. J. ; Hedrick J. L. ; Waymouth R. M. Organocatalysis: opportunities and challenges for polymer synthesis . Macromolecules , 2010 , 43 ( 5 ), 2093 - 2107 . doi: 10.1021/ma9025948 http://dx.doi.org/10.1021/ma9025948

Ottou W. N. ; Sardon H. ; Mecerreyes D. ; Vignolle J. ; Taton D. Update and challenges in organo-mediated polymerization reactions . Prog. Polym. Sci. , 2016 , 56 , 64 - 115 . doi: 10.1016/j.progpolymsci.2015.12.001 http://dx.doi.org/10.1016/j.progpolymsci.2015.12.001

Lin B. H. ; Waymouth R. M. Organic ring-opening polymerization catalysts: reactivity control by balancing acidity . Macromolecules , 2018 , 51 ( 8 ), 2932 - 2938 . doi: 10.1021/acs.macromol.8b00540 http://dx.doi.org/10.1021/acs.macromol.8b00540

Dharmaratne N. U. ; Pothupitiya J. U. ; Kiesewetter M. K. The mechanistic duality of (thio)urea organocatalysts for ring-opening polymerization . Org. Biomol. Chem. , 2019 , 17 ( 13 ), 3305 - 3313 . doi: 10.1039/c8ob03174f http://dx.doi.org/10.1039/c8ob03174f

Li M. S. ; Zhang S. ; Zhang X. Y. ; Wang Y. C. ; Chen J. L. ; Tao Y. H. ; Wang X. H. Unimolecular anion-binding catalysts for selective ring-opening polymerization of O-carboxyanhydrides . Angew. Chem. Int. Ed. , 2021 , 60 ( 11 ), 6003 - 6012 . doi: 10.1002/anie.202011352 http://dx.doi.org/10.1002/anie.202011352

Lv W. X. ; Wang Y. C. ; Li M. S. ; Wang X. H. ; Tao Y. H. Precision synthesis of polypeptides via living anionic ring-opening polymerization of N -carboxyanhydrides by tri-thiourea catalysts . J. Am. Chem. Soc. , 2022 , 144 ( 51 ), 23622 - 23632 . doi: 10.1021/jacs.2c10950 http://dx.doi.org/10.1021/jacs.2c10950

Miyamoto M. ; Sawamoto M. ; Higashimura T. Living polymerization of isobutyl vinyl ether with hydrogen iodide/iodine initiating system . Macromolecules , 1984 , 17 ( 3 ), 265 - 268 . doi: 10.1021/ma00133a001 http://dx.doi.org/10.1021/ma00133a001

Faust R. ; Kennedy J. P. Living carbocationic polymerization . Polym. Bull. , 1986 , 15 ( 4 ), 317 - 323 . doi: 10.1007/bf00254850 http://dx.doi.org/10.1007/bf00254850

Sawamoto M. Modern cationic vinyl polymerization . Prog. Polym. Sci. , 1991 , 16 ( 1 ), 111 - 172 . doi: 10.1016/0079-6700(91)90008-9 http://dx.doi.org/10.1016/0079-6700(91)90008-9

Matyjaszewski K. ; Sigwalt P. Unified approach to living and non-living cationic polymerization of alkenes . Polym. Int. , 1994 , 35 ( 1 ), 1 - 26 . doi: 10.1002/pi.1994.210350101 http://dx.doi.org/10.1002/pi.1994.210350101

Li M. S. ; Zhang Z. ; Yan Y. ; Lv W. X. ; Li Z. K. ; Wang X. H. ; Tao Y. H. Anion-binding catalysis enables living cationic polymerization . Nat. Synth. , 2022 , 1 , 815 - 823 . doi: 10.1038/s44160-022-00142-0 http://dx.doi.org/10.1038/s44160-022-00142-0

Li M. S. ; Li H. Y. ; Zhang X. Y. ; Wang X. H. ; Tao Y. H. Mechanistic insight into anion-binding catalytic living cationic polymerization . Angew. Chem. Int. Ed. , 2023 , 62 ( 26 ), e 202303237 . doi: 10.1002/anie.202303237 http://dx.doi.org/10.1002/anie.202303237

Davies W. H. 302. Anhydrocarboxy-derivatives of hydroxy- and mercapto-acids . J. Chem. Soc. , 1951 , 1357 . doi: 10.1039/jr9510001357 http://dx.doi.org/10.1039/jr9510001357

Farthing A. C. ; Reynolds R. J. W. Anhydro- N -carboxy- DL - β -phenylalanine . Nature , 1950 , 165 , 647 . doi: 10.1038/165647a0 http://dx.doi.org/10.1038/165647a0

Tighe B. J. Ring opening reactions of 5 , 5 -dimethyl-1,3-dioxolan-2,4 -dione . Chem. Ind. 1969, ( 51 ), 1837 .

Smith I. J. ; Tighe B. J. Studies in ring-opening polymerization. IV. Thermal polymerization of phenyl-substituted 1,3-dioxolan-2,4-diones . J. Polym. Sci. Polym. Chem. Ed. , 1976 , 14 ( 4 ), 949 - 960 . doi: 10.1002/pol.1976.170140415 http://dx.doi.org/10.1002/pol.1976.170140415

Smith I. J. ; Tighe B. J. S tudies in ring opening polymerisation, 6. Tertiary base initiated polymerisation of 5-phenyl-1,3-dioxolan-2,4-dione . Makromol. Chem. , 1981 , 182 ( 2 ), 313 - 324 . doi: 10.1002/macp.1981.021820204 http://dx.doi.org/10.1002/macp.1981.021820204

Kricheldorf H. ; Jonté J. New polymer syntheses . Polym. Bull. , 1983 , 9 , 276 - 283 .

Thillaye du Boullay O. ; Marchal E. ; Martin-Vaca B. ; Cossío F. P. ; Bourissou D. An activated equivalent of lactide toward organocatalytic ring-opening polymerization . J. Am. Chem. Soc. , 2006 , 128 ( 51 ), 16442 - 16443 . doi: 10.1021/ja067046y http://dx.doi.org/10.1021/ja067046y

Hillmyer M. A. ; Tolman W. B. Aliphatic polyester block polymers: renewable, degradable, and sustainable . Acc. Chem. Res. , 2014 , 47 ( 8 ), 2390 - 2396 . doi: 10.1021/ar500121d http://dx.doi.org/10.1021/ar500121d

Schneiderman D. K. ; Hillmyer M. A. 50 th Anniversary perspective: There is a great future in sustainable polymers . Macromolecules , 2017 , 50 ( 10 ), 3733 - 3749 . doi: 10.1021/acs.macromol.7b00293 http://dx.doi.org/10.1021/acs.macromol.7b00293

Haque F. M. ; Ishibashi J. S. A. ; Lidston C. A. L. ; Shao H. L. ; Bates F. S. ; Chang A. B. ; Coates G. W. ; Cramer C. J. ; Dauenhauer P. J. ; Dichtel W. R. ; Ellison C. J. ; Gormong E. A. ; Hamachi L. S. ; Hoye T. R. ; Jin M. Y. ; Kalow J. A. ; Kim H. J. ; Kumar G. ; LaSalle C. J. ; Liffland S. ; Lipinski B. M. ; Pang Y. T. ; Parveen R. ; Peng X. Y. ; Popowski Y. ; Prebihalo E. A. ; Reddi Y. ; Reineke T. M. ; Sheppard D. T. ; Swartz J. L. ; Tolman W. B. ; Vlaisavljevich B. ; Wissinger J. ; Xu S. ; Hillmyer M. A. Defining the macromolecules of tomorrow through synergistic sustainable polymer research . Chem. Rev. , 2022 , 122 ( 6 ), 6322 - 6373 . doi: 10.1021/acs.chemrev.1c00173 http://dx.doi.org/10.1021/acs.chemrev.1c00173

Dechy-Cabaret O. ; Martin-Vaca B. ; Bourissou D. Controlled ring-opening polymerization of lactide and glycolide . Chem. Rev. , 2004 , 104 ( 12 ), 6147 - 6176 . doi: 10.1021/cr040002s http://dx.doi.org/10.1021/cr040002s

Ovitt T. M. ; Coates G. W. Stereochemistry of lactide polymerization with chiral catalysts: new opportunities for stereocontrol using polymer exchange mechanisms . J. Am. Chem. Soc. , 2002 , 124 ( 7 ), 1316 - 1326 . doi: 10.1021/ja012052+ http://dx.doi.org/10.1021/ja012052+

Liao X. ; Su Y. ; Tang X. Y. Stereoselective synthesis of biodegradable polymers by salen-type metal catalysts . Sci. China Chem. , 2022 , 65 ( 11 ), 2096 - 2121 . doi: 10.1007/s11426-022-1377-5 http://dx.doi.org/10.1007/s11426-022-1377-5

Kamber N. E. ; Jeong W. ; Waymouth R. M. ; Pratt R. C. ; Lohmeijer B. G. G. ; Hedrick J. L. Organocatalytic ring-opening polymerization . Chem. Rev. , 2007 , 107 ( 12 ), 5813 - 5840 . doi: 10.1021/cr068415b http://dx.doi.org/10.1021/cr068415b

Martin Vaca B. ; Bourissou D. O-carboxyanhydrides: useful tools for the preparation of well-defined functionalized polyesters . ACS Macro Lett. , 2015 , 4 ( 7 ), 792 - 798 . doi: 10.1021/acsmacrolett.5b00376 http://dx.doi.org/10.1021/acsmacrolett.5b00376

Xie L. H. ; Tong R. ; Feng Q. Y. ; Zhong Y. L. Recent advances in ring-opening polymerization of O-carboxyanhydrides . Synlett , 2017 , 28 ( 15 ), 1857 - 1866 . doi: 10.1055/s-0036-1590841 http://dx.doi.org/10.1055/s-0036-1590841

Tong R. New chemistry in functional aliphatic polyesters . Ind. Eng. Chem. Res. , 2017 , 56 ( 15 ), 4207 - 4219 . doi: 10.1021/acs.iecr.7b00524 http://dx.doi.org/10.1021/acs.iecr.7b00524

Zhong Y. L. ; Tong R. Living ring-opening polymerization of O -carboxyanhydrides: the search for catalysts . Front. Chem. , 2018 , 6 , 641 . doi: 10.3389/fchem.2018.00641 http://dx.doi.org/10.3389/fchem.2018.00641

Wang X. Q. ; Chin A. L. ; Tong R. Controlled ring-opening polymerization of O -carboxyanhydrides to synthesize functionalized poly( α -hydroxy acids) . Org. Mater. , 2021 , 3 ( 1 ), 41 - 50 .

Yin Q. ; Yin L. C. ; Wang H. ; Cheng J. J. Synthesis and biomedical applications of functional poly( α -hydroxy acids) via ring-opening polymerization of O -carboxyanhydrides . Acc. Chem. Res. , 2015 , 48 ( 7 ), 1777 - 1787 . doi: 10.1021/ar500455z http://dx.doi.org/10.1021/ar500455z

Wang J. Q. ; Tao Y. H. Synthesis of sustainable polyesters via organocatalytic ring-opening polymerization of o -carboxyanhydrides: advances and perspectives . Macromol. Rapid Commun. , 2021 , 42 ( 3 ), 2000535 . doi: 10.1002/marc.202000535 http://dx.doi.org/10.1002/marc.202000535

Liang J. P. ; Yang J. Sequence-controlled copolymerization of salicylic O -carboxyanhydrides by organocatalysts . Macromolecules , 2024 , 57 ( 8 ), 3623 - 3635 . doi: 10.1021/acs.macromol.4c00563 http://dx.doi.org/10.1021/acs.macromol.4c00563

Thillaye du Boullay O. ; Bonduelle C. ; Martin-Vaca B. ; Bourissou D. Functionalized polyesters from organocatalyzed ROP of gluOCA, the O -carboxyanhydride derived from glutamic acid . Chem. Commun. , 2008 , ( 15 ), 1786 - 1788 . doi: 10.1039/b800852c http://dx.doi.org/10.1039/b800852c

Lu Y. B. ; Yin L. C. ; Zhang Y. F. ; Zhang Z. H. ; Xu Y. X. ; Tong R. ; Cheng J. J. Synthesis of water-soluble poly( α - hydroxy acids) from living ring-opening polymerization of O-benzyl-l-serine carboxyanhydrides . ACS Macro Lett. , 2012 , 1 ( 4 ), 441 - 444 . doi: 10.1021/mz200165c http://dx.doi.org/10.1021/mz200165c

Chen X. Y. ; Lai H. W. ; Xiao C. S. ; Tian H. Y. ; Chen X. S. ; Tao Y. H. ; Wang X. H. New bio-renewable polyester with rich side amino groups from l-lysine via controlled ring-opening polymerization . Polym. Chem. , 2014 , 5 ( 22 ), 6495 - 6502 . doi: 10.1039/c4py00930d http://dx.doi.org/10.1039/c4py00930d

Bonduelle C. ; Martín-Vaca B. ; Cossío F. P. ; Bourissou D. Monomer versus alcohol activation in the 4-dimethylaminopyridine-catalyzed ring-opening polymerization of lactide and lactic O-carboxylic anhydride . Chemistry , 2008 , 14 ( 17 ), 5304 - 5312 . doi: 10.1002/chem.200800346 http://dx.doi.org/10.1002/chem.200800346

Pounder R. J. ; Fox D. J. ; Barker I. A. ; Bennison M. J. ; Dove A. P. Ring-opening polymerization of an O -carboxyanhydride monomer derived from l-malic acid . Polym. Chem. , 2011 , 2 ( 10 ), 2204 - 2212 . doi: 10.1039/c1py00254f http://dx.doi.org/10.1039/c1py00254f

Buchard A. ; Carbery D. R. ; Davidson M. G. ; Ivanova P. K. ; Jeffery B. J. ; Kociok-Köhn G. I. ; Lowe J. P. Preparation of stereoregular isotactic poly(mandelic acid) through organocatalytic ring-opening polymerization of a cyclic O -carboxyanhydride . Angew. Chem. Int. Ed , 2014 , 53 ( 50 ), 13858 - 13861 . doi: 10.1002/anie.201407525 http://dx.doi.org/10.1002/anie.201407525

Bexis P. ; De Winter J. ; Coulembier O. ; Dove A. P. Isotactic degradable polyesters derived from O-carboxyanhydrides of l-lactic and l-malic acid using a single organocatalyst/initiator system . Eur. Polym. J. , 2017 , 95 , 660 - 670 . doi: 10.1016/j.eurpolymj.2017.05.038 http://dx.doi.org/10.1016/j.eurpolymj.2017.05.038

Wang R. B. ; Zhang J. W. ; Yin Q. ; Xu Y. X. ; Cheng J. J. ; Tong R. Controlled ring-opening polymerization of O -carboxyanhydrides using a β -diiminate zinc catalyst . Angew. Chem. Int. Ed. , 2016 , 55 ( 42 ), 13010 - 13014 . doi: 10.1002/anie.201605508 http://dx.doi.org/10.1002/anie.201605508

Sun Y. Y. ; Jia Z. W. ; Chen C. J. ; Cong Y. ; Mao X. Y. ; Wu J. C. Alternating sequence controlled copolymer synthesis of α‍-hydroxy acids via syndioselective ring-opening polymerization of O -carboxyanhydrides using zirconium/hafnium alkoxide initiators . J. Am. Chem. Soc. , 2017 , 139 ( 31 ), 10723 - 10732 . doi: 10.1021/jacs.7b04712 http://dx.doi.org/10.1021/jacs.7b04712

Cui Y. Q. ; Jiang J. X. ; Pan X. B. ; Wu J. C. Highly isoselective ring-opening polymerization of rac- O -carboxyanhydrides using a zinc alkoxide initiator . Chem. Commun. , 2019 , 55 ( 86 ), 12948 - 12951 . doi: 10.1039/c9cc06108h http://dx.doi.org/10.1039/c9cc06108h

Jiang J. X. ; Cui Y. Q. ; Lu Y. G. ; Zhang B. ; Pan X. B. ; Wu J. C. Weak lewis pairs as catalysts for highly isoselective ring-opening polymerization of epimerically labile rac - O -carboxyanhydride of mandelic acid . Macromolecules , 2020 , 53 ( 3 ), 946 - 955 . doi: 10.1021/acs.macromol.9b02302 http://dx.doi.org/10.1021/acs.macromol.9b02302

Feng Q. Y. ; Tong R. Controlled photoredox ring-opening polymerization of O -carboxyanhydrides . J. Am. Chem. Soc. , 2017 , 139 ( 17 ), 6177 - 6182 . doi: 10.1021/jacs.7b01462 http://dx.doi.org/10.1021/jacs.7b01462

Feng Q. Y. ; Yang L. ; Zhong Y. L. ; Guo D. ; Liu G. L. ; Xie L. H. ; Huang W. ; Tong R. Stereoselective photoredox ring-opening polymerization of O -carboxyanhydrides . Nat. Commun. , 2018 , 9 ( 1 ), 1559 . doi: 10.1038/s41467-018-03879-5 http://dx.doi.org/10.1038/s41467-018-03879-5

Zhong Y. L. ; Feng Q. Y. ; Wang X. Q. ; Chen J. ; Cai W. J. ; Tong R. Functionalized polyesters via stereoselective electrochemical ring-opening polymerization of O -carboxyanhydrides . ACS Macro Lett. , 2020 , 9 ( 8 ), 1114 - 1118 . doi: 10.1021/acsmacrolett.0c00364 http://dx.doi.org/10.1021/acsmacrolett.0c00364

Wang X. Q. ; Chin A. L. ; Zhou J. Y. ; Wang H. ; Tong R. Resilient poly( α‍ -hydroxy acids) with improved strength and ductility via scalable stereosequence-controlled polymerization . J. Am. Chem. Soc. , 2021 , 143 ( 40 ), 16813 - 16823 . doi: 10.1021/jacs.1c08802 http://dx.doi.org/10.1021/jacs.1c08802

MacMillan D. W. C. The advent and development of organocatalysis . Nature , 2008 , 455 ( 7211 ), 304 - 308 . doi: 10.1038/nature07367 http://dx.doi.org/10.1038/nature07367

Doyle A. G. ; Jacobsen E. N. Small-molecule H-bond donors in asymmetric catalysis . Chem. Rev. , 2007 , 107 ( 12 ), 5713 - 5743 . doi: 10.1021/cr068373r http://dx.doi.org/10.1021/cr068373r

Liu T. Q. ; Simmons T. L. ; Bohnsack D. A. ; MacKay M. E. ; Smith M. R. ; Baker G. L. Synthesis of polymandelide: a degradable polylactide derivative with polystyrene-like properties . Macromolecules , 2007 , 40 ( 17 ), 6040 - 6047 . doi: 10.1021/ma061839n http://dx.doi.org/10.1021/ma061839n

Taylor M. S. ; Jacobsen E. N. Asymmetric catalysis by chiral hydrogen-bond donors . Angew. Chem. Int. Ed. , 2006 , 45 ( 10 ), 1520 - 1543 . doi: 10.1002/anie.200503132 http://dx.doi.org/10.1002/anie.200503132

Miyabe H. ; Takemoto Y. Discovery and application of asymmetric reaction by multi-functional thioureas . Bull. Chem. Soc. Jpn. , 2008 , 81 ( 7 ), 785 - 795 . doi: 10.1246/bcsj.81.785 http://dx.doi.org/10.1246/bcsj.81.785

Chauhan P. ; Mahajan S. ; Kaya U. ; Hack D. ; Enders D. Bifunctional amine-squaramides: powerful hydrogen-bonding organocatalysts for asymmetric domino/cascade reactions . Adv. Synth. Catal. , 2015 , 357 ( 2-3 ), 253 - 281 . doi: 10.1002/adsc.201401003 http://dx.doi.org/10.1002/adsc.201401003

Takemoto Y. ; Yamaoka Y. ; Miyabe H. ; Yasui Y. Chiral-thiourea-catalyzed direct mannich reaction . Synthesis , 2007 , 2007( 16 ), 2571 - 2575 . doi: 10.1055/s-2007-983795 http://dx.doi.org/10.1055/s-2007-983795

Okino T. ; Hoashi Y. ; Takemoto Y. Enantioselective Michael reaction of malonates to nitroolefins catalyzed by bifunctional organocatalysts . J. Am. Chem. Soc. , 2003 , 125 ( 42 ), 12672 - 12673 . doi: 10.1021/ja036972z http://dx.doi.org/10.1021/ja036972z

Okino T. ; Hoashi Y. ; Furukawa T. ; Xu X. N. ; Takemoto Y. Enantio- and diastereoselective Michael reaction of 1 ,‍ 3 -dicarbonyl compounds to nitroolefins catalyzed by a bifunctional thiourea . J. Am. Chem. Soc., 2005, 127 ( 1 ), 119 - 125 . doi: 10.1021/ja044370p http://dx.doi.org/10.1021/ja044370p

Dove A. P. ; Pratt R. C. ; Lohmeijer B. G. G. ; Waymouth R. M. ; Hedrick J. L. Thiourea-based bifunctional organocatalysis: supramolecular recognition for living polymerization . J. Am. Chem. Soc. , 2005 , 127 ( 40 ), 13798 - 13799 . doi: 10.1021/ja0543346 http://dx.doi.org/10.1021/ja0543346

Zhu J. B. ; Chen E. Y. X. From meso-lactide to isotactic polylactide: epimerization by B/N lewis pairs and kinetic resolution by organic catalysts . J. Am. Chem. Soc. , 2015 , 137 ( 39 ), 12506 - 12509 . doi: 10.1021/jacs.5b08658 http://dx.doi.org/10.1021/jacs.5b08658

Geng X. W. ; Liu X. ; Yu Q. L. ; Zhang C. J. ; Zhang X. H. Advancing H-bonding organocatalysis for ring-opening polymerization: intramolecular activation of initiator/chain end . J. Am. Chem. Soc. , 2024 , 146 ( 37 ), 25852 - 25859 . doi: 10.1021/jacs.4c09394 http://dx.doi.org/10.1021/jacs.4c09394

Wang L. Y. ; Liu Y. Y. ; Shen Y. ; Li Z. B. Ring-opening polymerization of cyclic esters mediated by base/(thio)urea binary catalysts toward sustainable polyesters . Polym. Chem. , 2024 , 15 ( 38 ), 3832 - 3846 . doi: 10.1039/d4py00884g http://dx.doi.org/10.1039/d4py00884g

Zhang C. J. ; Wu H. L. ; Li Y. ; Yang J. L. ; Zhang X. H. Precise synthesis of sulfur-containing polymers via cooperative dual organocatalysts with high activity . Nat. Commun. , 2018 , 9 ( 1 ), 2137 . doi: 10.1038/s41467-018-04554-5 http://dx.doi.org/10.1038/s41467-018-04554-5

Zhang X. Y. ; Jones G. O. ; Hedrick J. L. ; Waymouth R. M. Fast and selective ring-opening polymerizations by alkoxides and thioureas . Nat. Chem. , 2016 , 8 ( 11 ), 1047 - 1053 . doi: 10.1038/nchem.2574 http://dx.doi.org/10.1038/nchem.2574

Zhang J. ; Lui K. H. ; Zunino R. ; Jia Y. ; Morodo R. ; Warlin N. ; Hedrick J. L. ; Talarico G. ; Waymouth R. M. Highly selective O -phenylene bisurea catalysts for ROP: stabilization of oxyanion transition state by a semiflexible hydrogen bond pocket . J. Am. Chem. Soc. , 2024 , 146 ( 32 ), 22295 - 22305 . doi: 10.1021/jacs.4c04740 http://dx.doi.org/10.1021/jacs.4c04740

Xia Y. N. ; Chen Y. ; Song Q. L. ; Hu S. Y. ; Zhao J. P. ; Zhang G. Z. Base-to-base organocatalytic approach for one-pot construction of poly(ethylene oxide)-based macromolecular structures . Macromolecules , 2016 , 49 ( 18 ), 6817 - 6825 . doi: 10.1021/acs.macromol.6b01542 http://dx.doi.org/10.1021/acs.macromol.6b01542

Jiang Z. L. ; Zhao J. P. ; Zhang G. Z. Ionic organocatalyst with a urea anion and tetra- n -butyl ammonium cation for rapid, selective, and versatile ring-opening polymerization of lactide . ACS Macro Lett. , 2019 , 8 ( 7 ), 759 - 765 . doi: 10.1021/acsmacrolett.9b00418 http://dx.doi.org/10.1021/acsmacrolett.9b00418

Li M. S. ; Tao Y. ; Tang J. D. ; Wang Y. C. ; Zhang X. Y. ; Tao Y. H. ; Wang X. H. Synergetic organocatalysis for eliminating epimerization in ring-opening polymerizations enables synthesis of stereoregular isotactic polyester . J. Am. Chem. Soc. , 2019 , 141 ( 1 ), 281 - 289 . doi: 10.1021/jacs.8b09739 http://dx.doi.org/10.1021/jacs.8b09739

Schreiner P. R. Metal-free organocatalysis through explicit hydrogen bonding interactions . Chem. Soc. Rev. , 2003 , 32 ( 5 ), 289 - 296 . doi: 10.1039/b107298f http://dx.doi.org/10.1039/b107298f

Aoshima S. ; Kanaoka S. A renaissance in living cationic polymerization . Chem. Rev. , 2009 , 109 ( 11 ), 5245 - 5287 . doi: 10.1021/cr900225g http://dx.doi.org/10.1021/cr900225g

Faust, R. Cationic polymerization of nonpolar vinyl monomers . In: Matyjaszewski, K.; Möller, M., eds. Polymer Science: A Comprehensive Reference . Amsterdam : Elsevier , 2012 . 501 - 526 . doi: 10.1016/b978-0-444-53349-4.00074-1 http://dx.doi.org/10.1016/b978-0-444-53349-4.00074-1

Uchiyama M. ; Satoh K. ; Kamigaito M. Cationic RAFT and DT polymerization . Prog. Polym. Sci. , 2022 , 124 , 101485 . doi: 10.1016/j.progpolymsci.2021.101485 http://dx.doi.org/10.1016/j.progpolymsci.2021.101485

Wu L. Q. ; Rondon B. ; Dym S. ; Wang W. Q. ; Chen K. R. ; Niu J. Regulating cationic polymerization: from structural control to life cycle management . Prog. Polym. Sci. , 2023 , 145 , 101736 . doi: 10.1016/j.progpolymsci.2023.101736 http://dx.doi.org/10.1016/j.progpolymsci.2023.101736

Chen Y. N. ; Zhang L. ; Jin Y. ; Lin X. R. ; Chen M. Recent advances in living cationic polymerization with emerging initiation/controlling systems . Macromol. Rapid Commun. , 2021 , 42 ( 13 ), e 2100148 . doi: 10.1002/marc.202100148 http://dx.doi.org/10.1002/marc.202100148

Singha S. ; Pan S. ; Tallury S. S. ; Nguyen G. ; Tripathy R. ; De P. Recent developments on cationic polymerization of vinyl ethers . ACS Polym. Au , 2024 , 4 ( 3 ), 189 - 207 . doi: 10.1021/acspolymersau.3c00055 http://dx.doi.org/10.1021/acspolymersau.3c00055

Zhu Y. ; Yu Z. P. ; Liu R. F. ; Jin Y. S. ; Shi Q. S. ; Wu Y. B. Recent advances in green cationic polymerization . J. Polym. Sci. , 2024 , 62 ( 11 ), 2549 - 2573 . doi: 10.1002/pol.20230971 http://dx.doi.org/10.1002/pol.20230971

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DOI：10.11777/j.issn1000-3304.2024.24271

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