聚合物添加剂调控手性化合物结晶拆分的研究进展

王兆旭; 陈艺夫; 李婧; 陶艺; 刘应泽; 叶曦翀; 宛新华

doi:10.11777/j.issn1000-3304.2025.25034

您当前的位置：

首页 >

文章列表页 >

聚合物添加剂调控手性化合物结晶拆分的研究进展

综述 | 更新时间：2025-05-08

- 聚合物添加剂调控手性化合物结晶拆分的研究进展
- Progress in the Crystallization Resolution of Chiral Compounds Aided by Polymeric Additives
- 高分子学报 2025年页码：1-14
- 作者机构：
  
  1.北京分子科学国家研究中心高分子化学与物理教育部重点实验室北京大学化学与分子工程学院北京 100871
  2.山西浙大新材料与化工研究院太原 030032
  3.金属材料强度国家重点实验室陕西省软物质国际联合研究中心西安交通大学材料科学与工程学院西安 710049
- 作者简介：
  
  [ "叶曦翀，男，1990年生. 西安交通大学副教授，2018年毕业于北京大学化学学院，并获得理学博士学位. 于2022年入职西安交通大学材料科学与工程学院，获聘副教授，博士生导师，入选西安交通大学青年拔尖人才计划. 以第一作者身份在Angew. Chem. Int. Ed.， Nat. Commun.，Aggregate，Small等国际知名刊物上发表论文十余篇. 主持国家自然科学基金面上项目、青年项目各一项，北京分子科学国家研究中心开放课题和陕西省重点研发计划各一项. 研究方向为光学活性功能高分子材料、手性识别、分离功能材料等." ]
  [ "宛新华，男，1964年生. 北京大学教授，1985、1991年分别于合肥工业大学、中国纺织大学，获工学学士和工学博士学位. 入选教育部长江学者奖励计划(特聘教授)、百千万人才工程国家级人选、教育部跨世纪优秀人才培养计划. 获国家杰出青年基金、国家自然科学奖(三等，排名2)、中国化学会高分子科学创新奖. 主要研究方向为手性功能材料、高性能高分子材料、有机/无机杂化材料等，已发表SCI收录论文270余篇，撰写6本英文书的章节. 现为Chinese Journal of Polymer Science执行副主编，Australian Journal of Chemistry副主编；Chirality，《高等学校化学学报》《功能高分子学报》《高分子材料科学与工程》编委." ]
- 基金信息：
  
  国家自然科学基金(基金号 52333008);石家庄·北京大学合作专项，北京大学博雅博士后项目，北京分子科学研究中心BMS Junior Fellow项目，国家资助博士后研究人员计划(GZC20230031)
- DOI：10.11777/j.issn1000-3304.2025.25034
  中图分类号：
- CSTR：32057.14.GFZXB.2025.7390
- 收稿日期：2025-02-12，
  
  录用日期：2025-03-31，
  
  网络出版日期：2025-05-07，
- 稿件说明：
移动端阅览
王兆旭, 陈艺夫, 李婧, 陶艺, 刘应泽, 叶曦翀, 宛新华. 聚合物添加剂调控手性化合物结晶拆分的研究进展. 高分子学报, doi: 10.11777/j.issn1000-3304.2025.25034

Wang, Z. X.; Chen, Y. F.; Li, J.; Tao, Y.; Liu, Y. Z.; Ye, X. C.; Wan, X. H. Progress in the crystallization resolution of chiral compounds aided by polymeric additives. Acta Polymerica Sinica, doi: 10.11777/j.issn1000-3304.2025.25034
王兆旭, 陈艺夫, 李婧, 陶艺, 刘应泽, 叶曦翀, 宛新华. 聚合物添加剂调控手性化合物结晶拆分的研究进展. 高分子学报, doi: 10.11777/j.issn1000-3304.2025.25034 DOI： CSTR： 32057.14.GFZXB.2025.7390.

Wang, Z. X.; Chen, Y. F.; Li, J.; Tao, Y.; Liu, Y. Z.; Ye, X. C.; Wan, X. H. Progress in the crystallization resolution of chiral compounds aided by polymeric additives. Acta Polymerica Sinica, doi: 10.11777/j.issn1000-3304.2025.25034 DOI： CSTR： 32057.14.GFZXB.2025.7390.

摘要

由于操作简便、成本低，结晶拆分目前仍然是工业上获得单一构型手性药物或其中间体的重要手段. 基于“量身定制”添加剂的逆向结晶方法适用底物范围大，拆分效率高，应用前景广阔. 本文重点介绍了逆向结晶过程中均聚物、共聚物、多糖衍生物、聚合物组装体以及高分子/纳米粒子杂化体系调控手性化合物立体选择性结晶的研究进展，讨论了聚合物添加剂的构效关系和高效回收策略，并对其今后发展提出一些看法.

Abstract

Among chiral resolution methods

crystallization resolution is still a frequency used methods for obtaining enantiomerically pure chiral drugs or their intermediates in pharmaceutical industry owing to its simple operation and low cost. The reverse crystallization with the assistance of "tailor-made" additives is suitable for a wide range of substrates

shows high resolution efficiency

and has broad application prospects. Recent research advancements in the field of crystallization resolution using polymeroc additives have been comprehensively reviewed in this article. It includes homopolymers

copolymers

polysaccharide derivatives

polymer assemblies

and polymer/nanoparticle hybrids. In addition

the structure-activity relationship and efficient recovery strategy of the polymeric additives are discussed

and the future development of polymeric additives is proposed.

关键词

Keywords

references

Sakai K. ; Hirayama N. ; Tamura R. Novel Optical Resolution Technologies. Springer, 2007 . doi: 10.1007/978-3-540-46320-7 http://dx.doi.org/10.1007/978-3-540-46320-7

Bredikhin A. A. ; Bredikhina Z. A. Stereoselective crystallization as a basis for single-enantiomer drug production . Chem. Eng. Technol. , 2017 , 40 ( 7 ), 1211 - 1220 . doi: 10.1002/ceat.201600649 http://dx.doi.org/10.1002/ceat.201600649

Kasprzyk-Hordern B. Pharmacologically active compounds in the environment and their chirality . Chem. Soc. Rev. , 2010 , 39 ( 11 ), 4466 - 4503 . doi: 10.1039/c000408c http://dx.doi.org/10.1039/c000408c

Núñez M. C. ; García-Rubiño M. E. ; Conejo-García A. ; Cruz-López O. ; Kimatrai M. ; Gallo M. A. ; Espinosa A. ; Campos J. M. Homochiral drugs: a demanding tendency of the pharmaceutical industry . Curr. Med. Chem. , 2009 , 16 ( 16 ), 2064 - 2074 . doi: 10.2174/092986709788682173 http://dx.doi.org/10.2174/092986709788682173

Lorenz H. ; Seidel-Morgenstern A. Processes to separate enantiomers . Angew. Chem. Int. Ed. , 2014 , 53 ( 5 ), 1218 - 1250 . doi: 10.1002/anie.201302823 http://dx.doi.org/10.1002/anie.201302823

Li Y. ; Kang S. M. ; Shi G. ; Chen Y. F. ; Li B. W. ; Zhang J. ; Wan X. H. Synthesis of proline-derived helical copolyacetylenes as chiral stationary phases for HPLC enantioseparation . Chinese J. Polym. Sci. , 2025 , 43 ( 1 ), 61 - 69 . doi: 10.1007/s10118-024-3249-7 http://dx.doi.org/10.1007/s10118-024-3249-7

Cascella F. ; Seidel-Morgenstern A. ; Lorenz H. Exploiting ternary solubility phase diagrams for resolution of enantiomers: an instructive example . Chem. Eng. Technol. , 2020 , 43 ( 2 ), 329 - 336 . doi: 10.1002/ceat.201900421 http://dx.doi.org/10.1002/ceat.201900421

Saseendran A. S. K. ; Jayaraj H. ; Kalathil K. K. ; Sarala A. S. Crystallisation based deracemisation and chiral resolution of small molecules . Chem. Asian J. , 2025 , Doi: 10.1002/asia.202401465 http://dx.doi.org/10.1002/asia.202401465

Gotrane D. M. ; Deshmukh R. D. ; Ranade P. V. ; Sonawane S. P. ; Bhawal B. M. ; Gharpure M. M. ; Gurjar M. K. A novel method for resolution of amlodipine . Org. Process Res. Dev. , 2010 , 14 ( 3 ), 640 - 643 . doi: 10.1021/op900283z http://dx.doi.org/10.1021/op900283z

Braga D. ; Degli Esposti L. ; Rubini K. ; Shemchuk O. ; Grepioni F. Ionic cocrystals of racemic and enantiopure histidine: an intriguing case of homochiral preference . Cryst. Growth Des. , 2016 , 16 ( 12 ), 7263 - 7270 . doi: 10.1021/acs.cgd.6b01426 http://dx.doi.org/10.1021/acs.cgd.6b01426

Shemchuk O. ; Song L. X. ; Robeyns K. ; Braga D. ; Grepioni F. ; Leyssens T. Solid-state chiral resolution mediated by stoichiometry: crystallizing etiracetam with ZnCl 2 . Chem. Commun. , 2018 , 54 ( 77 ), 10890 - 10892 . doi: 10.1039/c8cc06199h http://dx.doi.org/10.1039/c8cc06199h

Collet A. ; Brienne M. J. ; Jacques J. Optical resolution by direct crystallization of enantiomer mixtures . Chem. Rev. , 1980 , 80 ( 3 ), 215 - 230 . doi: 10.1021/cr60325a001 http://dx.doi.org/10.1021/cr60325a001

Mahieux J. ; Sanselme M. ; Harthong S. ; Melan C. ; Aronica C. ; Guy L. ; Coquerel G. Preparative resolution of (±)- bis -tetralone by means of autoseeded preferential crystallization induced by solvent evaporation (ASPre CISE) . Cryst. Growth Des. , 2013 , 13 ( 8 ), 3621 - 3631 . doi: 10.1021/cg400589u http://dx.doi.org/10.1021/cg400589u

Gendron F. X. ; Mahieux J. ; Sanselme M. ; Coquerel G. Resolution of baclofenium hydrogenomaleate by using preferential crystallization . A first case of complete solid solution at high temperature and a large miscibility gap in the solid state. Cryst. Growth Des. , 2019 , 19 ( 8 ), 4793 - 4801 . doi: 10.1021/acs.cgd.9b00665 http://dx.doi.org/10.1021/acs.cgd.9b00665

Temmel E. ; Eicke M. J. ; Cascella F. ; Seidel-Morgenstern A. ; Lorenz H. Resolution of racemic guaifenesin applying a coupled preferential crystallization-selective dissolution process: rational process development . Cryst. Growth Des. , 2019 , 19 ( 6 ), 3148 - 3157 . doi: 10.1021/acs.cgd.8b01660 http://dx.doi.org/10.1021/acs.cgd.8b01660

Hein J. E. ; Cao B. H. ; van der Meijden M. W. ; Leeman M. ; Kellogg R. M. Resolution of omeprazole using coupled preferential crystallization: efficient separation of a nonracemizable conglomerate salt under near-equilibrium conditions . Org. Process Res. Dev. , 2013 , 17 ( 6 ), 946 - 950 . doi: 10.1021/op400081c http://dx.doi.org/10.1021/op400081c

洪诗斌 , 袁耀锋 . 晶体形成与三维分子结构的相关性研究——2021年沃尔夫化学奖浅析 . 大学化学 , 2022 , 37 ( 1 ), 2104048 - 2104054 .

Addadi L. ; Berkovitch-Yellin Z. ; Domb N. ; Gati E. ; Lahav M. ; Leiserowitz L. Resolution of conglomerates by stereoselective habit modifications . Nature , 1982 , 296 ( 5852 ), 21 - 26 . doi: 10.1038/296021a0 http://dx.doi.org/10.1038/296021a0

Weissbuch I. ; Lahav M. ; Leiserowitz L. Toward stereochemical control, monitoring, and understanding of crystal nucleation . Cryst. Growth Des. , 2003 , 3 ( 2 ), 125 - 150 . doi: 10.1021/cg0200560 http://dx.doi.org/10.1021/cg0200560

Addadi L. ; Weinstein S. ; Gati E. ; Weissbuch I. ; Lahav M. Resolution of conglomerates with the assistance of tailor-made impurities . Generality and mechanistic aspects of the "rule of reversal". A new method for assignment of absolute configuration. J. Am. Chem. Soc. , 1982 , 104 ( 17 ), 4610 - 4617 . doi: 10.1021/ja00381a018 http://dx.doi.org/10.1021/ja00381a018

Zbaida D. ; Weissbuch I. ; Shavit-Gati E. ; Addadi L. ; Leiserowitz L. ; Lahav M. Design of chiral polymers for the kinetic resolution of racemic conglomerates . React. Polym. Ion Exch. Sorbents , 1987 , 6 ( 2-3 ), 241 - 253 . doi: 10.1016/0167-6989(87)90095-x http://dx.doi.org/10.1016/0167-6989(87)90095-x

Berfeld M. ; Zbaida D. ; Leiserowitz L. ; Lahav M. 'tailor-made' polymers for the removal of lamellar twinning: resolution of α -amino acids by entrainment . Adv. Mater. , 1999 , 11 ( 4 ), 328 - 331 . doi: 10.1002/(sici)1521-4095(199903)11:4<328::aid-adma328>3.0.co;2-v http://dx.doi.org/10.1002/(sici)1521-4095(199903)11:4<328::aid-adma328>3.0.co;2-v

Staab E. ; Addadi L. ; Leiserowitz L. ; Lahav M. Control of polymorphism by 'tailor-made' polymeric crystallization auxiliaries . Preferential precipitation of a metastable polar form for second harmonic generation. Adv. Mater. , 1990 , 2 ( 1 ), 40 - 43 . doi: 10.1002/adma.19900020108 http://dx.doi.org/10.1002/adma.19900020108

Weissbuch I. ; Zbaida D. ; Addadi L. ; Leiserowitz L. ; Lahav M. Design of polymeric inhibitors for the control of crystal polymorphism . Induced enantiomeric resolution at racemic histidine by crystallization at 25 ℃. J. Am. Chem. Soc ., 1987 , 109 ( 6 ), 1869 - 1871 . doi: 10.1021/ja00240a052 http://dx.doi.org/10.1021/ja00240a052

Li N. ; Wang H. ; Zhang J. ; Wan X. H. Controlled synthesis of chiral polymers for the kinetic resolution of racemic amino acids . Polym. Chem. , 2014 , 5 ( 5 ), 1702 - 1710 . doi: 10.1039/c3py01297b http://dx.doi.org/10.1039/c3py01297b

Ye X. C. ; Zhang J. ; Cui J. X. ; Wan X. H. Thermo-responsive recoverable polymeric inhibitors for the resolution of racemic amino acids . Chem. Commun. , 2018 , 54 ( 22 ), 2785 - 2787 . doi: 10.1039/c8cc00333e http://dx.doi.org/10.1039/c8cc00333e

Ye X. C. ; Wang Z. X. ; Zhang J. ; Wan X. H. Noncovalently functionalized commodity polymers as tailor-made additives for stereoselective crystallization . Angew. Chem. Int. Ed. , 2021 , 60 ( 37 ), 20243 - 20248 . doi: 10.1002/anie.202106603 http://dx.doi.org/10.1002/anie.202106603

Li J. ; Wang Z. ; Ye X. ; Wan X. Efficient preparation of "tailor-made" polymeric additives for the selective crystallization of racemates . Acta Polymerica Sinica , 2023 , 10.11777/j.issn1000-3304.2023.23091

Zhan J. ; Lin H. P. ; Mou C. Y. Biomimetic formation of porous single-crystalline CaCO 3 via nanocrystal aggregation . Adv. Mater. , 2003 , 15 ( 7-8 ), 621 - 623 . doi: 10.1002/adma.200304600 http://dx.doi.org/10.1002/adma.200304600

Antonietti M. ; Breulmann M. ; Göltner C. G. ; Cölfen H. ; Wong K. K. W. ; Walsh D. ; Mann S. Inorganic/organic mesostructures with complex architectures: precipitation of calcium phosphate in the presence of double-hydrophilic block copolymers . Chem. Eur. J. , 1998 , 4 ( 12 ), 2493 - 2500 . doi: 10.1002/(sici)1521-3765(19981204)4:12<2493::aid-chem2493>3.0.co;2-v http://dx.doi.org/10.1002/(sici)1521-3765(19981204)4:12<2493::aid-chem2493>3.0.co;2-v

Qi L. M. ; Cölfen H. ; Antonietti M. Crystal design of barium sulfate using double-hydrophilic block copolymers . Angew. Chem. Int. Ed. , 2000 , 39 ( 3 ), 604 - 607 . doi: 10.1002/(sici)1521-3773(20000204)39:3<604::aid-anie604>3.0.co;2-b http://dx.doi.org/10.1002/(sici)1521-3773(20000204)39:3<604::aid-anie604>3.0.co;2-b

Menahem T. ; Pravda M. ; Mastai Y. Correlation between structures of chiral polymers and their efficiency for chiral resolution by crystallization . Chirality , 2009 , 21 ( 9 ), 862 - 870 . doi: 10.1002/chir.20724 http://dx.doi.org/10.1002/chir.20724

Mastai Y. ; Sedlák M. ; Cölfen H. ; Antonietti M. The separation of racemic crystals into enantiomers by chiral block copolymers . Chem. Eur. J. , 2002 , 8 ( 11 ), 2429 - 2437 . doi: 10.1002/1521-3765(20020603)8:11<2429::aid-chem2429>3.0.co;2-6 http://dx.doi.org/10.1002/1521-3765(20020603)8:11<2429::aid-chem2429>3.0.co;2-6

Wohlrab S. ; Pinna N. ; Antonietti M. ; Cölfen H. Polymer-induced alignment of dl-alanine nanocrystals to crystalline mesostructures . Chem. Eur. J. , 2005 , 11 ( 10 ), 2903 - 2913 . doi: 10.1002/chem.200400420 http://dx.doi.org/10.1002/chem.200400420

Mori H. ; Matsuyama M. ; Endo T. Assembled structures and chiroptical properties of amphiphilic block copolymers synthesized by RAFT polymerization of N-acryloyl-L-alanine . Macromol. Chem. Phys. , 2008 , 209 ( 20 ), 2100 - 2112 . doi: 10.1002/macp.200800254 http://dx.doi.org/10.1002/macp.200800254

Kim B. S. ; Qiu J. M. ; Wang J. P. ; Andrew Taton T. Magnetomicelles: composite nanostructures from magnetic nanoparticles and cross-linked amphiphilic block copolymers . Nano Lett. , 2005 , 5 ( 10 ), 1987 - 1991 . doi: 10.1021/nl0513939 http://dx.doi.org/10.1021/nl0513939

Ladmiral V. ; Semsarilar M. ; Canton I. ; Armes S. P. Polymerization-induced self-assembly of galactose-functionalized biocompatible diblock copolymers for intracellular delivery . J. Am. Chem. Soc. , 2013 , 135 ( 36 ), 13574 - 13581 . doi: 10.1021/ja407033x http://dx.doi.org/10.1021/ja407033x

Ding L. ; Chen C. N. ; Deng J. P. ; Yang W. T. Optically active thermosensitive amphiphilic polymer brushes based on helical polyacetylene: preparation through "click" onto grafting method and self-assembly . Polym. Bull. , 2012 , 69 ( 9 ), 1023 - 1040 . doi: 10.1007/s00289-012-0790-2 http://dx.doi.org/10.1007/s00289-012-0790-2

Tan J. J. ; Li Y. X. ; Liu R. G. ; Kang H. L. ; Wang D. Q. ; Ma L. ; Liu W. Y. ; Wu M. ; Huang Y. Micellization and sustained drug release behavior of EC- g -PPEGMA amphiphilic copolymers . Carbohydr. Polym. , 2010 , 81 ( 2 ), 213 - 218 . doi: 10.1016/j.carbpol.2010.02.017 http://dx.doi.org/10.1016/j.carbpol.2010.02.017

Yang L. ; Tang Y. ; Liu N. ; Liu C. H. ; Ding Y. S. ; Wu Z. Q. Facile synthesis of hybrid silica nanoparticles grafted with helical poly(phenyl isocyanide)s and their enantioselective crystallization ability . Macromolecules , 2016 , 49 ( 20 ), 7692 - 7702 . doi: 10.1021/acs.macromol.6b01870 http://dx.doi.org/10.1021/acs.macromol.6b01870

Ye X. C. ; Cui J. X. ; Li B. W. ; Li N. ; Zhang J. ; Wan X. H. Self-reporting inhibitors: a single crystallization process to obtain two optically pure enantiomers . Angew. Chem. Int. Ed. , 2018 , 57 ( 27 ), 8120 - 8124 . doi: 10.1002/anie.201803480 http://dx.doi.org/10.1002/anie.201803480

Li B. W. ; Li N. ; Wang Z. X. ; Ye X. C. ; Zhang J. ; Wan X. H. High-performance nano-splitters containing aggregation-induced emission luminogens for stereoselective crystallization obtained via polymerization-induced self-assembly . Aggregate , 2021 , 2 ( 6 ), e 129 . doi: 10.1002/agt2.129 http://dx.doi.org/10.1002/agt2.129

Ye X. C. ; Cui J. X. ; Li B. W. ; Li N. ; Wang R. ; Yan Z. J. ; Tan J. Y. ; Zhang J. ; Wan X. H. Enantiomer-selective magnetization of conglomerates for quantitative chiral separation . Nat. Commun. , 2019 , 10 , 1964 . doi: 10.1038/s41467-019-09997-y http://dx.doi.org/10.1038/s41467-019-09997-y

Medina D. D. ; Goldshtein J. ; Margel S. ; Mastai Y. Enantioselective crystallization on chiral polymeric microspheres . Adv. Funct. Mater. , 2007 , 17 ( 6 ), 944 - 950 . doi: 10.1002/adfm.200600408 http://dx.doi.org/10.1002/adfm.200600408

Chen B. ; Deng J. P. ; Yang W. T. Hollow two-layered chiral nanoparticles consisting of optically active helical polymer/silica: preparation and application for enantioselective crystallization . Adv. Funct. Mater. , 2011 , 21 ( 12 ), 2345 - 2350 . doi: 10.1002/adfm.201100113 http://dx.doi.org/10.1002/adfm.201100113

Zhang D. ; Song C. ; Deng J. ; Yang W. Chiral microspheres consisting purely of optically active helical substituted polyacetylene: the first preparation via precipitation polymerization and application in enantioselective crystallization . Macromolecules , 2012 , 45 ( 18 ), 7329 - 7338 . doi: 10.1021/ma301250u http://dx.doi.org/10.1021/ma301250u

Xiao Y. ; Wang H. Q. ; Zhang H. ; Jiang Z. Q. ; Wang Y. Q. ; Li H. ; Yin J. ; Zhu Y. Y. ; Wu Z. Q. Grafting polymerization of single-handed helical poly(phenyl isocyanide)s on graphene oxide and their application in enantioselective separation . J. Polym. Sci. Part A Polym. Chem. , 2017 , 55 ( 12 ), 2092 - 2103 . doi: 10.1002/pola.28599 http://dx.doi.org/10.1002/pola.28599

Xu L. ; Wu Y. J. ; Gao R. T. ; Li S. Y. ; Liu N. ; Wu Z. Q. Visible helicity induction and memory in polyallene toward circularly polarized luminescence, helicity discrimination, and enantiomer separation . Angew. Chem. Int. Ed. , 2023 , 62 ( 13 ), e 202217234 . doi: 10.1002/anie.202217234 http://dx.doi.org/10.1002/anie.202217234

Ilevbare G. A. ; Liu H. Y. ; Edgar K. J. ; Taylor L. S. Understanding polymer properties important for crystal growth inhibition: impact of chemically diverse polymers on solution crystal growth of ritonavir . Cryst. Growth Des. , 2012 , 12 ( 6 ), 3133 - 3143 . doi: 10.1021/cg300325p http://dx.doi.org/10.1021/cg300325p

Schram C. J. ; Beaudoin S. P. ; Taylor L. S. Impact of polymer conformation on the crystal growth inhibition of a poorly water-soluble drug in aqueous solution . Langmuir , 2015 , 31 ( 1 ), 171 - 179 . doi: 10.1021/la503644m http://dx.doi.org/10.1021/la503644m

Petrova R. I. ; Swift J. A. Selective growth and distribution of crystalline enantiomers in hydrogels . J. Am. Chem. Soc. , 2004 , 126 ( 4 ), 1168 - 1173 . doi: 10.1021/ja0392263 http://dx.doi.org/10.1021/ja0392263

Alexander A. J. Crystallization of sodium chlorate with d -glucose co-solute is not enantios elective . Cryst. Growth Des. , 2008 , 8 ( 8 ), 2630 - 2632 . doi: 10.1021/cg800540z http://dx.doi.org/10.1021/cg800540z

Jiang L. ; Titmuss S. ; Cowley A. ; Klein J. Direct measurement of forces between cell-coating polymers and chiral crystal surfaces: the enantioselectivity of hyaluronan . Soft Matter , 2008 , 4 ( 7 ), 1521 - 1530 . doi: 10.1039/b717940e http://dx.doi.org/10.1039/b717940e

Wang Z. X. ; Ye X. C. ; Chen Y. F. ; Liu Y. Z. ; Xie S. Y. ; Tao Y. ; Zhang J. ; Wan X. H. Stereoselective crystallization of chiral pharmaceuticals aided by cellulose derivatives through helical pattern matching . Chem. Eur. J. , 2024 , 30 ( 49 ), e 202401550 . doi: 10.1002/chem.202401550 http://dx.doi.org/10.1002/chem.202401550

浏览量

下载量

CSCD

文章被引用时，请邮件提醒。

提交

工具集

关联资源

基于超临界溶剂热法的共价有机框架单晶超快制备

透射电子显微镜在聚合物不同层次结构研究中的应用

多金属氧簇-聚合物复合物磁共振成像及光热-化学治疗性质

聚合物热激活延迟荧光材料的分子设计与器件性能

聚集诱导发光聚合物