Cascade RAFT Polymerization of Hetero Diels-Alder Cycloaddition Reaction

Ruyue Cao; Jingjing Xiao; Yixuan Wang; Xiangyu Li; Anchao Feng; Liqun Zang

doi:10.7536/PC221129

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Prog Chem ›› 2023, Vol. 35 ›› Issue (5) : 721-734. DOI: 10.7536/PC221129

Review

Cascade RAFT Polymerization of Hetero Diels-Alder Cycloaddition Reaction

Ruyue Cao ¹^,²^,³ ,
Jingjing Xiao ¹^,²^,³ ,
Yixuan Wang ¹^,²^,³ ,
Xiangyu Li ¹^,²^,³ ,
Anchao Feng ¹^,²^,³^,^* ,
Liqun Zang ¹^,²^,³

Author information +

History +

Abstract

Diels-Alder (DA) reaction is temperature-reversible, catalyst-free, efficient and fast with none harmful products, making it a favorable choice to build a self-healing and recyclable dynamic covalent elastomer network. However, classic DA reactions (such as the reaction between furan and maleimide) still have the problems of long reaction time, low efficiency and poor chemical modularity. Recent studies have shown that the efficient cascade of HDA reaction (Diels-Alder cycloaddition reaction containing heteroatom sulfur) and RAFT polymerization can be realized by highly reactive dienes reacting with specific RAFT agents, which can reduce the reaction temperature and time of DA. By virtue of the RAFT polymerization, it can control polymer molecular weight and its distribution at the same time. RAFT-HDA cascade reaction shows wide potential applications especially in the preparation of high molecular weight block or grafted polymer and surface modification. In this paper, the research and application of HDA-RAFT cascade reaction in the past 15 years are summarized, existing problems and solutions are discussed and the future development of this field is also prospected.

Contents

1 Introduction

2 RAFT-HDA reaction between cyclic conjugated diene and BPDF/BDEPDF

2.1 Preparation of high molecular weight copolymer by chain extension

2.2 Material surface finish

2.3 self healing and Self reporting materials

2.4 crosslinking networks with thermally reversible Crosslinking sites

3 RAFT-HDA reaction between linear conjugated diene and BPDF/BDEPDF

3.1 Preparation of high molecular weight copolymer by chain extension

3.2 Material surface finish

3.3 self healing and Self reporting materials

3.4 crosslinking networks with thermally reversible Crosslinking sites

4 Others

5 Conclusion and outlooks

Key words

hetero Diels-Alder cycloaddition reaction / RAFT polymerization / graft polymer / surface modification

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Ruyue Cao , Jingjing Xiao , Yixuan Wang , et al . Cascade RAFT Polymerization of Hetero Diels-Alder Cycloaddition Reaction[J]. Progress in Chemistry. 2023, 35(5): 721-734 https://doi.org/10.7536/PC221129

References

List( Publishing order | Descend order by publishing year | Descend order by cited within ) Chart analysis

[1]	Ouchi M, Terashima T, Sawamoto M. Chem. Rev., 2009, 109(11): 4963. Cited in this article [1]

[2]	Braunecker W A, Matyjaszewski K. Prog. Polym. Sci., 2007, 32(1): 93. Cited in this article [1]

[3]	Moad G, Rizzardo E, Thang S H. Aust. J. Chem., 2012, 65(8): 985. Cited in this article [1]

[4]	Moad G, Rizzardo E, Thang S H. Polymer, 2008, 49(5): 1079. Cited in this article [1]

[5]	Inglis A J, Barner-kowollik C. Macromol. Rapid Commun., 2010, 31(14): 1247. Cited in this article [1]

[6]	Adzima B J, Bowman C N. AIChE J., 2012, 58(10): 2952. Cited in this article [1]

[7]	Masson G, Lalli C, Benohoud M. Chem. Soc. Rev., 2013, 42(3): 902. Cited in this article [1]

[8]	Tasdelen M A. Polym. Chem., 2011, 2(10): 2133. Cited in this article [1]

[9]	Wang Z P, Yuan J Y. Prog. Chem., 2012, 24(12): 2342. Cited in this article [1]

[10]	Knall A C, Slugovc C. Chem. Soc. Rev., 2013, 42(12): 5131. Cited in this article [1]

[11]	Inglis A J, Stenzel M H, Barner-kowollik C. Macromol. Rapid Commun., 2009, 30(21): 1792. Cited in this article [3]

[12]	Espinosa E, Glassner M, Boisson C. Macromol. Rapid Commun., 2011, 32(18): 1447. Cited in this article [1]

[13]	Langer M, Brandt J, Lederer A, Goldmann A S, Schacher F H, Barner-Kowollik C. Polym. Chem., 2014, 5(18): 5330. Cited in this article [3]

[14]	Dürr C J, Hlalele L, Kaiser A, Brandau S, Barner-Kowollik C. Macromolecules, 2013, 46(1): 49. Cited in this article [3]

[15]	Glassner M, Delaittre G, Kaupp M, Blinco J P, Barner-Kowollik C. J. Am. Chem. Soc., 2012, 134(17): 7274. Cited in this article [1]

[16]	Kawaguchi H. Prog. Polym. Sci., 2000, 25(8): 1171. Cited in this article [1]

[17]	Zhu J M, Li P. J. Polym. Sci. A Polym. Chem., 2003, 41(21): 3346. Cited in this article [1]

[18]	Blomberg S, Ostberg S, Harth E, Bosman A W, Van Horn B, Hawker C J. J. Polym. Sci. A Polym. Chem., 2002, 40(9): 1309. Cited in this article [1]

[19]	Voccia S, JÉrôme C, Detrembleur C, Leclère P, Gouttebaron R, Hecq M, Gilbert B, Lazzaroni R, JÉrôme R. Chem. Mater., 2003, 15(4): 923. Cited in this article [1]

[20]	Parvole J, Montfort J P, Reiter G, Borisov O, Billon L. Polymer, 2006, 47(4): 972. Cited in this article [1]

[21]	Garcia F G, Pinto M R, Soares B G. Eur. Polym. J., 2002, 38(4): 759. Cited in this article [1]

[22]	Vivek A V, Dhamodharan R. J. Polym. Sci. A Polym. Chem., 2007, 45(17): 3818. Cited in this article [1]

[23]	Inoue Y, Matsugi T, Kashiwa N, Matyjaszewski K. Macromolecules, 2004, 37(10): 3651. Cited in this article [1]

[24]	Li Y, Schadler L S, Benicewicz B C. Handbook of RAFT Polymerization. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2008. 423. Cited in this article [1]

[25]	Quinn J F, Davis T P, Barner L, Barner-Kowollik C. Polymer, 2007, 48(22): 6467. Cited in this article [1]

[26]	Nebhani L, Schmiedl D, Barner L, Barner-Kowollik C. Adv. Funct. Mater., 2010, 20(12): 2010. Cited in this article [3]

[27]	Tischer T, Goldmann A S, Linkert K, Trouillet V, Börner H G, Barner-Kowollik C. Adv. Funct. Mater., 2012, 22(18): 3853. Cited in this article [3]

[28]	Spitalsky Z, Tasis D, Papagelis K, Galiotis C. Prog. Polym. Sci., 2010, 35(3): 357. Cited in this article [1]

[29]	Zydziak N, Hübner C, Bruns M, Barner-Kowollik C. Macromolecules, 2011, 44(9): 3374. Cited in this article [1]

[30]	Zydziak N, Preuss C M, Winkler V, Bruns M, Hübner C, Barner-Kowollik C. Macromol. Rapid Commun., 2013, 34(8): 672. Cited in this article [1]

[31]	Kaupp M, Vogt A P, Natterodt J C, Trouillet V, Gruendling T, Hofe T, Barner L, Barner-Kowollik C. Polym. Chem., 2012, 3(9): 2605. Cited in this article [1]

[32]	Ge G, Lu Y, Qu X. ACS Nano, 2020, 14(1): 218. Cited in this article [1]

[33]	Zhang F, Ju P F, Pan M Q, Zhang D W, Huang Y, Li G L, Li X G. Corros. Sci., 2018, 144: 74. Cited in this article [1]

[34]	Wang H, Wang P P, Feng Y P, Liu J, Wang J Q, Hu M M, Wei J, Huang Y. ChemElectroChem, 2019, 6(6): 1605. Cited in this article [1]

[35]	Döhler D, Michael P, Binder W H. Acc. Chem. Res., 2017, 50(10): 2610. Cited in this article [1]

[36]	Zhang Q H, Niu S M, Wang L, Lopez J, Chen S C, Cai Y F, Du R C, Liu Y X, Lai J C, Liu L, Li C H, Yan X Z, Liu C G, Tok J B H, Jia X D, Bao Z N. Adv. Mater., 2018, 30(33): 1801435. Cited in this article [1]

[37]	Mutlu H, Schmitt C W, Wedler-Jasinski N, Woehlk H, Fairfull-Smith K E, Blinco J P, Barner-Kowollik C. Polym. Chem., 2017, 8(40): 6199. Cited in this article [1]

[38]	Guimard N K, Ho J, Brandt J, Lin C Y, Namazian M, Mueller J O, Oehlenschlaeger K K, Hilf S, Lederer A, Schmidt F G, Coote M L, Barner-Kowollik C. Chem. Sci., 2013, 4(7): 2752. Cited in this article [1]

[39]	Schenzel A M, Klein C, Rist K, Moszner N, Barner-Kowollik C. Adv. Sci., 2016, 3(3): 1500361. Cited in this article [1]

[40]	Inglis A J, Sinnwell S, Davis T P, Barner-Kowollik C, Stenzel M H. Macromolecules, 2008, 41(12): 4120. Cited in this article [3]

[41]	Sinnwell S, Inglis A J, Davis T P, Stenzel M H, Barner-Kowollik C. Chem. Commun., 2008, (17): 2052. Cited in this article [1]

[42]	Sinnwell S, Inglis A J, Stenzel M H, Barner-Kowollik C. Macromol. Rapid Commun., 2008, 29(12/13): 1090. Cited in this article [1]

[43]	Sinnwell S, Lammens M, Stenzel M H, Du Prez F E, Barner-Kowollik C. J. Polym. Sci. A Polym. Chem., 2009, 47(8): 2207.S. Cited in this article [1]

[44]	Bousquet A, Barner-Kowollik C, Stenzel M H. J. Polym. Sci. A Polym. Chem., 2010, 48(8): 1773. Cited in this article [3]

[45]	Wang Z J, Ma Z Y, Zhang Z Y, Wu F, Jiang H, Jia X R. Polym. Chem., 2014, 5(24): 6893. Cited in this article [1]

[46]	Nebhani L, Sinnwell S, Inglis A J, Stenzel M H, Barner-Kowollik C, Barner L. Macromol. Rapid Commun., 2008, 29(17): 1431. Cited in this article [3]

[47]	Nebhani L, Gerstel P, Atanasova P, Bruns M, Barner-Kowollik C. J. Polym. Sci. A Polym. Chem., 2009, 47(24): 7090. Cited in this article [1]

[48]	Le Droumaguet B, Nicolas J. Polym. Chem., 2010, 1(5): 563. Cited in this article [1]

[49]	Gauthier M A, Klok H A. Polym. Chem., 2010, 1(9): 1352. Cited in this article [1]

[50]	Ko J H, Maynard H D. Chem. Soc. Rev., 2018, 47(24): 8998. Cited in this article [1]

[51]	Wright T A, Page R C, Konkolewicz D. Polym. Chem., 2019, 10(4): 434. Cited in this article [1]

[52]	Beloqui A, Mane S R, Langer M, Glassner M, Bauer D M, Fruk L, Barner-Kowollik C, Delaittre G. Angew. Chem. Int. Ed., 2020, 59(45): 19951. Cited in this article [1]

[53]	Zhou J W, Guimard N K, Inglis A J, Namazian M, Lin C Y, Coote M L, Spyrou E, Hilf S, Schmidt F G, Barner-Kowollik C. Polym. Chem., 2012, 3(3): 628. Cited in this article [1]

[54]	Rajappan S C, Davis B J, Dishner I T, Thornell T L, Peyrefitte J J, Simon Y C. Polym. Chem., 2022, 13(6): 741. Cited in this article [3]

[55]	Nebhani L, Sinnwell S, Lin C Y, Coote M L, Stenzel M H, Barner-Kowollik C. J. Polym. Sci. A Polym. Chem., 2009, 47(22): 6053. Cited in this article [1]

[56]	Oehlenschlaeger K K, Mueller J O, Heine N B, Glassner M, Guimard N K, Delaittre G, Schmidt F G, Barner-Kowollik C. Angew. Chem. Int. Ed., 2013, 52(2): 762. Cited in this article [3]