Non-activated Esters as Reactive Handles in Direct Post-Polymerization Modification

被引:17
作者
Van Guyse, Joachim F. R. [1 ,2 ]
Bernhard, Yann [1 ,3 ]
Podevyn, Annelore [1 ]
Hoogenboom, Richard [1 ]
机构
[1] Univ Ghent, Ctr Macromol Chem CMaC, Dept Organ & Macromol Chem, Supramol Chem Grp, Krijgslaan 281 S4, B-9000 Ghent, Belgium
[2] Leiden Univ, Leiden Acad Ctr Drug Res LACDR, Einsteinweg 55, NL-2333 CC Leiden, Netherlands
[3] Univ Lorraine, Fac Sci & Technol, CNRS, UMR 7053,L2CM, BP 70239, F-54506 Vandoeuvre Les Nancy, France
基金
日本学术振兴会;
关键词
Amidation; Catalysis; Polymers; Post-Polymerization Modification; Transesterification; RING-OPENING POLYMERIZATION; BIOSYNTHETIC POLY(GAMMA-GLUTAMIC ACID); CROSS-LINKED POLYMERS; BENZYL-L-GLUTAMATE; PS-B-PMMA; THERMOTROPIC POLYPEPTIDES; POLYACRYLOYL HYDRAZIDE; BLOCK-COPOLYMERS; ACYL TRANSFER; SELECTIVE TRANSESTERIFICATION;
D O I
10.1002/anie.202303841
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Non-activated esters are prominently featured functional groups in polymer science, as ester functional monomers display great structural diversity and excellent compatibility with a wide range of polymerization mechanisms. Yet, their direct use as a reactive handle in post-polymerization modification has been typically avoided due to their low reactivity, which impairs the quantitative conversion typically desired in post-polymerization modification reactions. While activated ester approaches are a well-established alternative, the modification of non-activated esters remains a synthetic and economically valuable opportunity. In this review, we discuss past and recent efforts in the utilization of non-activated ester groups as a reactive handle to facilitate transesterification and aminolysis/amidation reactions, and the potential of the developed methodologies in the context of macromolecular engineering.
引用
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页数:16
相关论文
共 214 条
[1]   BASE-CATALYZED FORMATION OF CYCLIC COMPOUNDS FROM POLY-BETA-BENZYL-L-ASPARTATE AND POLY-GAMMA-BENZYL-L-GLUTAMATE [J].
ADLER, AJ ;
FASMAN, GD ;
BLOUT, ER .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (01) :90-&
[2]   An emerging post-polymerization modification technique: The promise of thiol-para-fluoro click reaction [J].
Agar, Soykan ;
Baysak, Elif ;
Hizal, Gurkan ;
Tunca, Umit ;
Durmaz, Hakan .
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2018, 56 (12) :1181-1198
[3]   Facile Approach to Grafting of Poly(2-oxazoline) Brushes on Macroscopic Surfaces and Applications Thereof [J].
Agrawal, Mukesh ;
Carlos Rueda, Juan ;
Uhlmann, Petra ;
Mueller, Martin ;
Simon, Frank ;
Stamm, Manfred .
ACS APPLIED MATERIALS & INTERFACES, 2012, 4 (03) :1357-1364
[4]  
Ajekwene K., 2020, Acrylate Polymers for Advanced Applications, P35
[5]   Synthesis and pharmacological activity of a novel water-soluble hepatocyte-specific polymeric prodrug of prostaglandin E1 using lactosylated poly(L-glutamic hydrazide) as a carrier [J].
Akamatsu, K ;
Yamasaki, Y ;
Nishikawa, M ;
Takakura, Y ;
Hashida, M .
BIOCHEMICAL PHARMACOLOGY, 2001, 62 (11) :1531-1536
[6]   Nitroxide-mediated polymerisation of thioacrylates and their transformation into poly(acrylamide)s [J].
Aksakal, Suzan ;
Liu, Renjie ;
Aksakal, Resat ;
Becer, C. Remzi .
POLYMER CHEMISTRY, 2020, 11 (05) :982-989
[7]   Thioester functional polymers [J].
Aksakal, Suzan ;
Aksakal, Resat ;
Becer, C. Remzi .
POLYMER CHEMISTRY, 2018, 9 (36) :4507-4516
[8]   Poly(thioacrylate)s: expanding the monomer toolbox of functional polymers [J].
Aksakal, Suzan ;
Becer, C. Remzi .
POLYMER CHEMISTRY, 2016, 7 (45) :7011-7018
[9]   Self-healing PEG-poly(aspartic acid) hydrogel with rapid shape recovery and drug release [J].
An, Heng ;
Zhu, Linmiao ;
Shen, Jiafu ;
Li, Wenjuan ;
Wang, Yong ;
Qin, Jianglei .
COLLOIDS AND SURFACES B-BIOINTERFACES, 2020, 185
[10]  
Bae Y, 2005, MOL BIOSYST, V1, P242, DOI 10.1039/b500266d