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Open AccessOpen Access JUSTC Chemistry 02 July 2022

Exploring the topological effect of linear and cyclic macroCTAs during polymerization-induced self-assembly (PISA)

  • CAS Key Laboratory of Soft Matter Chemistry, Department of Polymer Science and Engineering, University of Science and Technology of China, Hefei 230026, China

Cite this:
https://doi.org/10.52396/JUSTC-2022-0040
More Information
  • Author Bio:

    Depeng Yin is currently a postgraduate student in CAS Key Laboratory of Soft Matter Chemistry, Department of Polymer Science and Engineering under the supervision of Prof. Chunyan Hong at the University of Science and Technology of China. His research mainly focuses on polymerization induced self-assembly

    Chao Liu is currently a postdoctoral fellow at the University of Science and Technology of China (USTC). He received his Ph.D. in Chemistry from USTC in 2019 under the supervision of Profs. Chunyan Hong and Caiyuan Pan. He then joined Prof. Chunyan Hong's group as a postdoctoral fellow in July 2019. His scientific interests include the synthesis of topological polymers and polymerization-induced self-assembly

    Chunyan Hong is a Professor at the University of Science and Technology of China (USTC). She obtained her Ph.D. in Chemistry from USTC in 2002. Her research interests include controlled radical polymerization, the synthesis of stimuli responsive polymers and biodegradable polymers, the fabrication of functionalized nanomaterials, and their applications in drug or gene delivery

  • Corresponding author: E-mail: liuchao216@ustc.edu.cn; E-mail: hongcy@ustc.edu.cn
  • Received Date: 28 February 2022
  • Accepted Date: 02 April 2022
    • Available Online: 02 July 2022
    Abstract

  • Abstract

    Polymerization-induced self-assembly (PISA) is a robust strategy for the syntheses of block copolymer nano-objects with various morphologies. Although PISA has been extensively studied, the use of cyclic macromolecular chain transfer agents (macroCTAs) as the hydrophilic block has not been reported. We explored the effects of macroCTA topology on the polymerization kinetics and morphologies of block copolymer assemblies during reversible addition-fragmentation chain transfer (RAFT) dispersion polymerization. To this end, linear and cyclic poly (ethylene oxide) (PEO) with 4-(4-cyanopentanoic acid) dithiobenzoate (CPADB) groups were synthesized and used as CTAs to mediate the RAFT polymerization of benzyl methacrylate (BzMA) and 2,3,4,5,6-pentafluorostyrene (PFSt) under PISA formulation. Interestingly, the nucleation period of the linear PEO is slightly shorter than that of its cyclic analog, and the cyclic hydrophilic segment leads to a delayed morphological transition during PISA.

    Graphical abstract

    The cyclic hydrophilic segment can delay the morphological transition of block copolymer nanoparticles during PISA compared with the linear analog.

    Abstract

    Polymerization-induced self-assembly (PISA) is a robust strategy for the syntheses of block copolymer nano-objects with various morphologies. Although PISA has been extensively studied, the use of cyclic macromolecular chain transfer agents (macroCTAs) as the hydrophilic block has not been reported. We explored the effects of macroCTA topology on the polymerization kinetics and morphologies of block copolymer assemblies during reversible addition-fragmentation chain transfer (RAFT) dispersion polymerization. To this end, linear and cyclic poly (ethylene oxide) (PEO) with 4-(4-cyanopentanoic acid) dithiobenzoate (CPADB) groups were synthesized and used as CTAs to mediate the RAFT polymerization of benzyl methacrylate (BzMA) and 2,3,4,5,6-pentafluorostyrene (PFSt) under PISA formulation. Interestingly, the nucleation period of the linear PEO is slightly shorter than that of its cyclic analog, and the cyclic hydrophilic segment leads to a delayed morphological transition during PISA.

    • Public Summary

    • A cyclic macromolecular chain transfer agent (macroCTA) was synthesized via UV-induced cyclization.
    • The effects of the topological structures of macroCTA on the polymerization kinetics and morphologies of block copolymer assemblies during reversible addition fragmentation chain transfer (RAFT) dispersion polymerization were explored.
    • The cyclic hydrophilic segment could lead to a longer nucleation period and delay the morphology transition of block copolymer nanoparticles during PISA.

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    • References(44)
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    [17]
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    Discher D E, Eisenberg A. Polymer vesicles. Science, 2002, 297 (5583): 967–973. doi: 10.1126/science.1074972
    [22]
    Tian H, Qin J, Hou D, et al. General interfacial self-assembly engineering for patterning two-dimensional polymers with cylindrical mesopores on graphene. Angew. Chem. Int. Ed., 2019, 131 (30): 10279–10284. doi: 10.1002/ange.201903684
    [23]
    Wang Z, Van Oers M C, Rutjes F P, et al. Polymersome colloidosomes for enzyme catalysis in a biphasic system. Angew. Chem. Int. Ed., 2012, 124 (43): 10904–10908. doi: 10.1002/ange.201206555
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    Zhang L, Shen H, Eisenberg A. Phase separation behavior and crew-cut micelle formation of polystyrene-b-poly (acrylic acid) copolymers in solutions. Macromolecules, 1997, 30 (4): 1001–1011. doi: 10.1021/ma961413g
    [25]
    Liu F, Eisenberg A. Preparation and pH triggered inversion of vesicles from poly (acrylic acid)-block-polystyrene-block-Poly (4-vinyl pyridine). J. Am. Chem. Soc., 2003, 125 (49): 15059–15064. doi: 10.1021/ja038142r
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    Foster J C, Varlas S, Couturaud B, et al. Getting into shape: Reflections on a new generation of cylindrical nanostructures’ self-assembly using polymer building blocks. J. Am. Chem. Soc., 2019, 141 (7): 2742–2753. doi: 10.1021/jacs.8b08648
    [27]
    D'agosto F, Rieger J, Lansalot M. RAFT-mediated polymerization-induced self-assembly. Angew. Chem. Int. Ed., 2020, 59 (22): 8368–8392. doi: 10.1002/anie.201911758
    [28]
    Cornel E J, Jiang J, Chen S, et al. Principles and characteristics of polymerization-induced self-assembly with various polymerization techniques. CCS Chem., 2021, 3 (4): 2104–2125. doi: 10.31635/ccschem.020.202000470
    [29]
    Zeng M, Zhou S, Sui X, et al. Effect of solvophilic chain length in PISA particles on Pickering emulsion. Chin. J. Chem., 2021, 39 (12): 3448–3454. doi: 10.1002/cjoc.202100457
    [30]
    Cai W B, Liu D D, Chen Y, et al. Enzyme-assisted photoinitiated polymerization-induced self-assembly in continuous flow reactors with oxygen tolerance. Chinese J. Polym. Sci., 2021, 39 (9): 1127–1137. doi: 10.1007/s10118-021-2533-z
    [31]
    Charleux B, Delaittre G, Rieger J, et al. Polymerization-induced self-assembly: From soluble macromolecules to block copolymer nano-objects in one step. Macromolecules, 2012, 45 (17): 6753–6765. doi: 10.1021/ma300713f
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    Penfold N J, Yeow J, Boyer C, et al. Emerging trends in polymerization-induced self-assembly. ACS Macro Lett., 2019, 8 (8): 1029–1054. doi: 10.1021/acsmacrolett.9b00464
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    Zhang Y, Han G, Cao M, et al. Influence of solvophilic homopolymers on RAFT polymerization-induced self-assembly. Macromolecules, 2018, 51 (11): 4397–4406. doi: 10.1021/acs.macromol.8b00690
    [37]
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    [41]
    Yamamoto T, Yagyu S, Tezuka Y. Light-and heat-triggered reversible linear–cyclic topological conversion of telechelic polymers with anthryl end groups. J. Am. Chem. Soc., 2016, 138 (11): 3904–3911. doi: 10.1021/jacs.6b00800
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    Tang Q, Wu Y, Sun P, et al. Powerful ring-closure method for preparing varied cyclic polymers. Macromolecules, 2014, 47 (12): 3775–3781. doi: 10.1021/ma500799w
    [43]
    Warren N J, Mykhaylyk O O, Mahmood D, et al. RAFT aqueous dispersion polymerization yields poly (ethylene glycol)-based diblock copolymer nano-objects with predictable single phase morphologies. J. Am. Chem. Soc., 2014, 136 (3): 1023–1033. doi: 10.1021/ja410593n
    [44]
    Gao L, Ji Z, Zhao Y, et al. Synthesis and solution self-assembly properties of cyclic rod–coil diblock copolymers. ACS Macro Lett., 2019, 8 (12): 1564–1569. doi: 10.1021/acsmacrolett.9b00747
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    1..  Synthesis of LPEO-CPADB and CPEO-CPADB.

    2..  Synthesis of diblock copolymer nano-objects via polymerization-induced self-assembly (PISA) using (a) CPEO-CPADB and (b) LPEO-CPADB as macroCTA, respectively.

    Figure  1.  1H-NMR spectra of LPEO-CPADB (a) and CPEO-CPADB (b) (in CDCl3).

    Figure  2.  GPC traces of LPEO-CPADB and CPEO-CPADB with THF as eluent.

    Figure  3.  Polymerizations were conducted using [BzMA]0 : [macro-RAFT agent]0 : [AIBN]0 = 400:1:0.4. 1H-NMR spectra of PEO-b-PBzMA recorded during the RAFT dispersion polymerization of BzMA using (a) LPEO-CPADB and (b) CPEO-CPADB as the macroCTA in an ethanol/water mixture (70/30, w/w). Solid concentration, 10% w/w (in CDCl3).

    Figure  4.  Conversion vs. time (black line) and ln([M]0/[M]t) vs. time (red line) plots of BzMA during the RAFT dispersion polymerization using (a) LPEO-CPADB and (c) CPEO-CPADB as the macroCTA. GPC traces of (b) LPEO-b-PBzMA and (d) CPEO-b-PBzMA copolymers were obtained at different polymerization times.

    Figure  5.  TEM images of the PEO-b-PBzMA copolymer nano-objects with different DPs of PBzMA in the ethanol/water mixture (70/30, w/w), and the solid content = 20% (w/w).

    Figure  6.  TEM images of the PEO-b-PPFSt copolymer nano-objects with different DPs of PPFSt in the ethanol/DMF mixture (95/5, w/w), and the solid content = 25% (w/w).

    [1]
    Bielawski C W, Benitez D, Grubbs R H. An" endless" route to cyclic polymers. Science, 2002, 297 (5589): 2041–2044. doi: 10.1126/science.1075401
    [2]
    Gonsales S A, Kubo T, Flint M K, et al. Highly tactic cyclic polynorbornene: Stereoselective ring expansion metathesis polymerization of norbornene catalyzed by a new tethered tungsten-alkylidene catalyst. J. Am. Chem. Soc., 2016, 138 (15): 4996–4999. doi: 10.1021/jacs.6b00014
    [3]
    Nadif S S, Kubo T, Gonsales S A, et al. Introducing “Ynene” metathesis: Ring-expansion metathesis polymerization leads to highly cis and syndiotactic cyclic polymers of norbornene. J. Am. Chem. Soc., 2016, 138 (20): 6408–6411. doi: 10.1021/jacs.6b03247
    [4]
    Roland C D, Li H, Abboud K A, et al. Cyclic polymers from alkynes. Nat. Chem., 2016, 8 (8): 791–796. doi: 10.1038/nchem.2516
    [5]
    Culkin D A, Jeong W, Csihony S, et al. Zwitterionic polymerization of lactide to cyclic poly (lactide) by using N-heterocyclic carbene organocatalysts. Angew. Chem. Int. Ed., 2007, 119 (15): 2681–2684. doi: 10.1002/ange.200604740
    [6]
    Kapnistos M, Lang M, Vlassopoulos D, et al. Unexpected power-law stress relaxation of entangled ring polymers. Nat. Mater., 2008, 7 (12): 997–1002. doi: 10.1038/nmat2292
    [7]
    Di Marzio E A, Guttman C M. The glass temperature of polymer rings. Macromolecules, 1987, 20 (6): 1403–1407. doi: 10.1021/ma00172a040
    [8]
    Clarson S, Semlyen J. Cyclic polysiloxanes: 1. Preparation and characterization of poly (phenylmethylsiloxane). Polymer, 1986, 27 (10): 1633–1636. doi: 10.1016/0032-3861(86)90115-1
    [9]
    Hadziioannou G, Cotts P, Ten Brinke G, et al. Thermodynamic and hydrodynamic properties of dilute solutions of cyclic and linear polystyrenes. Macromolecules, 1987, 20 (3): 493–497. doi: 10.1021/ma00169a006
    [10]
    Jang S S, Çağin T, Goddard III W A. Effect of cyclic chain architecture on properties of dilute solutions of polyethylene from molecular dynamics simulations. J. Chem. Phys., 2003, 119 (3): 1843–1854. doi: 10.1063/1.1580802
    [11]
    Tezuka Y, Oike H. Topological polymer chemistry: Systematic classification of nonlinear polymer topologies. J. Am. Chem. Soc., 2001, 123 (47): 11570–11576. doi: 10.1021/ja0114409
    [12]
    Tezuka Y, Mori K, Oike H. Efficient synthesis of cyclic poly (oxyethylene) by electrostatic self-assembly and covalent fixation with telechelic precursor having cyclic ammonium salt groups. Macromolecules, 2002, 35 (14): 5707–5711. doi: 10.1021/ma020182c
    [13]
    Yamamoto T, Tezuka Y. Topological polymer chemistry: A cyclic approach toward novel polymer properties and functions. Polym. Chem., 2011, 2 (9): 1930–1941. doi: 10.1039/c1py00088h
    [14]
    Kimura A, Hasegawa T, Yamamoto T, et al. ESA-CF synthesis of linear and cyclic polymers having densely appended perylene units and topology effects on their thin-film electron mobility. Macromolecules, 2016, 49 (16): 5831–5840. doi: 10.1021/acs.macromol.6b01225
    [15]
    Laurent B A, Grayson S M. Synthetic approaches for the preparation of cyclic polymers. Chem. Soc. Rev., 2009, 38 (8): 2202–2213. doi: 10.1039/b809916m
    [16]
    Trachsel L, Romio M, Grob B, et al. Functional nanoassemblies of cyclic polymers show amplified responsiveness and enhanced protein-binding ability. ACS Nano, 2020, 14 (8): 10054–10067. doi: 10.1021/acsnano.0c03239
    [17]
    Honda S, Yamamoto T, Tezuka Y. Topology-directed control on thermal stability: Micelles formed from linear and cyclized amphiphilic block copolymers. J. Am. Chem. Soc., 2010, 132 (30): 10251–10253. doi: 10.1021/ja104691j
    [18]
    Honda S, Yamamoto T, Tezuka Y. Tuneable enhancement of the salt and thermal stability of polymeric micelles by cyclized amphiphiles. Nat. Commun., 2013, 4 (1): 1574. doi: 10.1038/ncomms2585
    [19]
    Discher B M, Won Y Y, Ege D S, et al. Polymersomes: Tough vesicles made from diblock copolymers. Science, 1999, 284 (5417): 1143–1146. doi: 10.1126/science.284.5417.1143
    [20]
    Mai Y, Eisenberg A. Self-assembly of block copolymers. Chem. Soc. Rev., 2012, 41 (18): 5969–5985. doi: 10.1039/c2cs35115c
    [21]
    Discher D E, Eisenberg A. Polymer vesicles. Science, 2002, 297 (5583): 967–973. doi: 10.1126/science.1074972
    [22]
    Tian H, Qin J, Hou D, et al. General interfacial self-assembly engineering for patterning two-dimensional polymers with cylindrical mesopores on graphene. Angew. Chem. Int. Ed., 2019, 131 (30): 10279–10284. doi: 10.1002/ange.201903684
    [23]
    Wang Z, Van Oers M C, Rutjes F P, et al. Polymersome colloidosomes for enzyme catalysis in a biphasic system. Angew. Chem. Int. Ed., 2012, 124 (43): 10904–10908. doi: 10.1002/ange.201206555
    [24]
    Zhang L, Shen H, Eisenberg A. Phase separation behavior and crew-cut micelle formation of polystyrene-b-poly (acrylic acid) copolymers in solutions. Macromolecules, 1997, 30 (4): 1001–1011. doi: 10.1021/ma961413g
    [25]
    Liu F, Eisenberg A. Preparation and pH triggered inversion of vesicles from poly (acrylic acid)-block-polystyrene-block-Poly (4-vinyl pyridine). J. Am. Chem. Soc., 2003, 125 (49): 15059–15064. doi: 10.1021/ja038142r
    [26]
    Foster J C, Varlas S, Couturaud B, et al. Getting into shape: Reflections on a new generation of cylindrical nanostructures’ self-assembly using polymer building blocks. J. Am. Chem. Soc., 2019, 141 (7): 2742–2753. doi: 10.1021/jacs.8b08648
    [27]
    D'agosto F, Rieger J, Lansalot M. RAFT-mediated polymerization-induced self-assembly. Angew. Chem. Int. Ed., 2020, 59 (22): 8368–8392. doi: 10.1002/anie.201911758
    [28]
    Cornel E J, Jiang J, Chen S, et al. Principles and characteristics of polymerization-induced self-assembly with various polymerization techniques. CCS Chem., 2021, 3 (4): 2104–2125. doi: 10.31635/ccschem.020.202000470
    [29]
    Zeng M, Zhou S, Sui X, et al. Effect of solvophilic chain length in PISA particles on Pickering emulsion. Chin. J. Chem., 2021, 39 (12): 3448–3454. doi: 10.1002/cjoc.202100457
    [30]
    Cai W B, Liu D D, Chen Y, et al. Enzyme-assisted photoinitiated polymerization-induced self-assembly in continuous flow reactors with oxygen tolerance. Chinese J. Polym. Sci., 2021, 39 (9): 1127–1137. doi: 10.1007/s10118-021-2533-z
    [31]
    Charleux B, Delaittre G, Rieger J, et al. Polymerization-induced self-assembly: From soluble macromolecules to block copolymer nano-objects in one step. Macromolecules, 2012, 45 (17): 6753–6765. doi: 10.1021/ma300713f
    [32]
    Penfold N J, Yeow J, Boyer C, et al. Emerging trends in polymerization-induced self-assembly. ACS Macro Lett., 2019, 8 (8): 1029–1054. doi: 10.1021/acsmacrolett.9b00464
    [33]
    Jennings J, He G, Howdle S M, et al. Block copolymer synthesis by controlled/living radical polymerisation in heterogeneous systems. Chem. Soc. Rev., 2016, 45 (18): 5055–5084. doi: 10.1039/C6CS00253F
    [34]
    Cai W, Wan W, Hong C, et al. Morphology transitions in RAFT polymerization. Soft Matter, 2010, 6 (21): 5554–5561. doi: 10.1039/c0sm00284d
    [35]
    Sun J T, Hong C Y, Pan C Y. Recent advances in RAFT dispersion polymerization for preparation of block copolymer aggregates. Polym. Chem., 2013, 4 (4): 873–881. doi: 10.1039/C2PY20612A
    [36]
    Zhang Y, Han G, Cao M, et al. Influence of solvophilic homopolymers on RAFT polymerization-induced self-assembly. Macromolecules, 2018, 51 (11): 4397–4406. doi: 10.1021/acs.macromol.8b00690
    [37]
    Huo M, Zeng M, Li D, et al. Tailoring the multicompartment nanostructures of fluoro-containing ABC triblock terpolymer assemblies via polymerization-induced self-assembly. Macromolecules, 2017, 50 (20): 8212–8220. doi: 10.1021/acs.macromol.7b01629
    [38]
    Li D, Huo M, Liu L, et al. Overcoming kinetic trapping for morphology evolution during polymerization-induced self-assembly. Macromol. Rapid Commun., 2019, 40 (16): 1900202. doi: 10.1002/marc.201900202
    [39]
    Zhang W J, Hong C Y, Pan C Y. Fabrication of electrospinning fibers from spiropyran-based polymeric nanowires and their photochromic properties. Macromol. Chem. Phys., 2013, 214 (21): 2445–2453. doi: 10.1002/macp.201300428
    [40]
    Liu C, Fei Y Y, Zhang H L, et al. Effective construction of hyperbranched multicyclic polymer by combination of ATRP, UV-induced cyclization, and self-accelerating click reaction. Macromolecules, 2019, 52 (1): 176–184. doi: 10.1021/acs.macromol.8b02192
    [41]
    Yamamoto T, Yagyu S, Tezuka Y. Light-and heat-triggered reversible linear–cyclic topological conversion of telechelic polymers with anthryl end groups. J. Am. Chem. Soc., 2016, 138 (11): 3904–3911. doi: 10.1021/jacs.6b00800
    [42]
    Tang Q, Wu Y, Sun P, et al. Powerful ring-closure method for preparing varied cyclic polymers. Macromolecules, 2014, 47 (12): 3775–3781. doi: 10.1021/ma500799w
    [43]
    Warren N J, Mykhaylyk O O, Mahmood D, et al. RAFT aqueous dispersion polymerization yields poly (ethylene glycol)-based diblock copolymer nano-objects with predictable single phase morphologies. J. Am. Chem. Soc., 2014, 136 (3): 1023–1033. doi: 10.1021/ja410593n
    [44]
    Gao L, Ji Z, Zhao Y, et al. Synthesis and solution self-assembly properties of cyclic rod–coil diblock copolymers. ACS Macro Lett., 2019, 8 (12): 1564–1569. doi: 10.1021/acsmacrolett.9b00747
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