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Progress in Chemistry 2022, Vol. 34 Issue (10): 2159-2172 DOI: 10.7536/PC220306 Previous Articles   Next Articles

• Review •

Application of Deep Eutectic Solvents in Polymer Synthesis

Li Jintao, Zhang Mingzu, He Jinlin(), Ni Peihong   

  1. College of Chemistry, Chemical Engineering and Materials Science, State and Local Joint Engineering Laboratory for Novel Functional Polymeric Materials, Jiangsu Key Laboratory of Advanced Functional Polymer Design and Application, Suzhou Key Laboratory of Macromolecular Design and Precision Synthesis, Soochow University,Suzhou 215123, China
  • Received: Revised: Online: Published:
  • Contact: He Jinlin
  • Supported by:
    National Natural Science Foundation of China(21774081); Natural Science Foundation of the Jiangsu Higher Education Institutions of China(20KJA150009); Beijing Key Lab of Special Elastomeric Composite Materials, and the Priority Academic Development of Jiangsu Higher Education Institutions.
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Deep eutectic solvents (DES) are one kind of low-transition-temperature mixture composed of two or several components mixed in a certain ratio. The melting points of DES are significantly lower than that of each pure component, and they can be considered as a new type of ionic liquid. Compared with traditional organic solvents, DES possess the advantages of broad resource of raw materials, low cost, easy preparation, low toxicity and biodegradability. These characteristics make them become a promising green reaction media, which have been widely used in many areas including extraction and separation, inorganic synthesis, organic synthesis and ion gels. In recent years, the applications of DES in polymer chemistry have attracted broad research interests. Starting from a brief description of DES and their applications in organic synthesis, this review mainly focuses on the applications of DES in polymerizations, such as condensation polymerization, free radical polymerization, anionic polymerization, electrochemical polymerization, ring-opening polymerization and oxidative polymerization. In the meantime, the prospects of DES in polymer synthesis are also discussed.

Key words: green chemistry, deep eutectic solvents, polymerization, polymeric materials, reaction media
Table 1 General formula for the classification of DES
Type General Formula Terms
Ⅰ Cat+X-zMClx M=Zn, Sn, Fe, Al, Ga, In
Ⅱ Cat+X-zMClx yH2O M=Cr, Co, Cu, Ni, Fe
Ⅲ Cat+X-zRZ Z=CONH2, COOH, OH
Ⅳ MClx+RZ=MC l x - 1 +·
RZ+MC l x + 1 -		 M=Al, Zn and Z=CONH2,
OH
Fig. 1 Typical structures of hydrogen bond acceptors (HBA) and hydrogen bond donors (HBD) for the preparation of DES
Fig. 2 Nucleophilic addition reactions of organometallic reagents in DES[39,41,42,44]
Fig. 3 DES-assisted synthesis of biodegradable antibacterial poly(octanediol-co-citrate)[57]. (a) Preparation of the different DES; (b) DES-assisted synthesis of POC elastomers containing antibacterial compounds; (c) diagram of the synthesis of POC. Copyright 2013, American Chemical Society
Fig. 4 Synthesis and application of photopolymerizable ChCl/AA-type DES. (a) One-step synthesis and its rapid, in-situ polymerization as a transparent, stretchable and conductive elastomer and (b) starfish-shaped tactile sensor[70]. Copyright 2017, The Royal Society of Chemistry. (c) Conductive paper[71]. Copyright 2018, The Royal Society of Chemistry. (d) Patterned optoelectronic devices using transparent piezoresistive balls[72]. Copyright 2020, The Royal Society of Chemistry. (e) Conductive fibers[73]. Copyright 2021, American Chemical Society
Fig. 5 All-in-one molecular networks design concept for autonomously self-healable transparent, stretchable, and conducive elastomers[74]. (a) Chemical structure and optical image of the poly(AAm/ChCl-co-MA/ChCl) elastomers; (b) demonstration of the healing process below zero temperature. Copyright 2020, American Chemical Society
Fig. 6 Fabrication of highly transparent, stretchable, self-healable, and conducive elastomers by the introduction of phytic acid as the hydrogen bonding crosslinker into PDES systems. (a) Design concept for ChCl/AA/PA-type PDES[75]. Copyright 2020, Elsevier. (b) Design concept for TMAC/AA/PA-type PDES[76]. Copyright 2021, The Royal Society of Chemistry
Fig. 7 The ATRP reaction of methyl acrylate displayed “living”/controlled character[91]. Copyright 2016, Wiley Periodicals, Inc
Fig. 8 RAFT polymerizations conducted in the DES of ChCl/Urea. (a) Homopolymerization of HEMA; (b) block copolymerization of HEMA and MMA[97]. Copyright 2019, Wiley Periodicals, Inc
Fig. 9 Organolithium-initiated anionic polymerization of olefins in ChCl-based DES[103]. Copyright 2019, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Fig. 10 Electrochemical polymerization mechanism of pyrrole in ChCl/Urea-type DES[117]. Copyright 2020, Elsevier B. V
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