Skip to main content
SpringerLink
Log in

Acyclic Diene Metathesis (ADMET) as Powerful Tool for Functional Polymers with Versatile Architectures

  • Topical Reviews
  • Published:
Journal of Inorganic and Organometallic Polymers and Materials Aims and scope Submit manuscript

Abstract

Since the discovery of acyclic diene metathesis (ADMET), researchers have gradually developed ADMET polymerization into a mature methodology for the preparation of versatile polymers with various precise functional groups. As a representative stepwise polymerization method, ADMET enable the polymerization of relatively “inert” acyclic diene monomers. By rational design of monomer structures, the resulted functional materials can be used in various fields such as biomedicine, optoelectronics and stimulus responsive materials. This review will focus on the synthetic strategies of functional polymers with various precise moieties by ADMET over the past few decades, especially functional polyesters, polyethers, polyolefins, and conjugated polymers as well as organometallic polymers will be summarized.

Graphical Abstract

Acyclic diene metathesis not only provides facile method for the polymerization of relatively “inert” acyclic diene monomers, but also gives polymers with versatile architectures and functionalities that cannot prepared via conventional polymerization methods. This comprehensive review summarizes the rational design of monomers for ADMET polymerization and corresponding synthesis of functional polyesters, polyethers, polyolefins, and conjugated polymers as well as organometallic polymers.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11
Fig. 12
Fig. 13

Copyright 2018, American Chemical Society

Fig. 14
Fig. 15
Fig. 16

Similar content being viewed by others

References

  1. J. Peng, B. Chen, Z. Wang, J. Guo, B. Wu, S. Hao, Q. Zhang, L. Gu, Q. Zhou, Z. Liu, S. Hong, S. You, A. Fu, Z. Shi, H. Xie, D. Cao, C.-J. Lin, G. Fu, L.-S. Zheng, Y. Jiang, N. Zheng, Surface coordination layer passivates oxidation of copper. Nature 586(7829), 390–394 (2020)

    Article  CAS  PubMed  Google Scholar 

  2. A.B. Cook, S. Perrier, Branched and dendritic polymer architectures: functional nanomaterials for therapeutic delivery. Adv. Funct. Mater. 30(2), 1901001 (2020)

    Article  CAS  Google Scholar 

  3. A. Das, P. Theato, Activated ester containing polymers: opportunities and challenges for the design of functional macromolecules. Chem. Rev. 116(3), 1434–1495 (2016)

    Article  CAS  PubMed  Google Scholar 

  4. G.R. Whittell, M.D. Hager, U.S. Schubert, I. Manners, Functional soft materials from metallopolymers and metallosupramolecular polymers. Nature Mater. 10(3), 176–188 (2011)

    Article  CAS  Google Scholar 

  5. R.G. Chaudhary, H.D. Juneja, M.P. Gharpure, Thermal degradation behaviour of some metal chelate polymer compounds with bis(bidentate) ligand by TG/DTG/DTA. J. Therm. Anal. Calorim. 112(2), 637–647 (2013)

    Article  CAS  Google Scholar 

  6. R.G. Chaudhary, H.D. Juneja, N.V. Gandhare, Evaluation of kinetic parameters from TG/DTG data of chelate polymer compounds of isophthaoyl bis (paramethoxyphenylcarbamide). J. Chin. Adv. Mater. Soc. 1(4), 305–316 (2013)

    Article  CAS  Google Scholar 

  7. M.A. Haque, R.G. Chaudhary, L.J. Paliwal, Synthesis, structural, morphological, and thermal decomposition kinetics of Iron (II) coordination polymer of sebacoyl bis (isonicotinoylhydrazone). Inorganica Chim. Acta 462, 298–307 (2017)

    Article  CAS  Google Scholar 

  8. J. Yan, H. Huang, Z. Miao, Q. Zhang, Y. Yan, Polyoxometalate-based hybrid supramolecular polymer via orthogonal metal coordination and reversible photo-cross-linking. Macromolecules 52(24), 9545–9554 (2019)

    Article  CAS  Google Scholar 

  9. D. Baskaran, A.H.E. Mueller, Anionic vinyl polymerization - 50 years after Michael Szwarc. Prog. Polym. Sci. 32(2), 173–219 (2007)

    Article  CAS  Google Scholar 

  10. N. Hadjichristidis, M. Pitsikalis, S. Pispas, H. Iatrou, Polymers with complex architecture by living anionic polymerization. Chem. Rev. 101(12), 3747–3792 (2001)

    Article  CAS  PubMed  Google Scholar 

  11. R. Barbey, L. Lavanant, D. Paripovic, N. Schuewer, C. Sugnaux, S. Tugulu, H.-A. Klok, Polymer brushes via surface-initiated controlled radical polymerization: synthesis, characterization, properties, and applications. Chem. Rev. 109(11), 5437–5527 (2009)

    Article  CAS  PubMed  Google Scholar 

  12. M.F. Cunningham, Controlled/living radical polymerization in aqueous dispersed systems. Prog. Polym. Sci. 33(4), 365–398 (2008)

    Article  CAS  Google Scholar 

  13. W.A. Braunecker, K. Matyjaszewski, Controlled/living radical polymerization: Features, developments, and perspectives. Prog. Polym. Sci. 32(1), 93–146 (2007)

    Article  CAS  Google Scholar 

  14. G. Moad, E. Rizzardo, S.H. Thang, End-functional polymers, thiocarbonylthio group removal/transformation and reversible addition-fragmentation-chain transfer (RAFT) polymerization. Polym. Int. 60(1), 9–25 (2011)

    Article  CAS  Google Scholar 

  15. S. Perrier, P. Takolpuckdee, Macromolecular design via reversible addition-fragmentation chain transfer (RAFT)/Xanthates (MADIX) polymerization. J. Polym. Sci. Part A 43(22), 5347–5393 (2005)

    Article  CAS  Google Scholar 

  16. X. Liu, F. Liu, W. Liu, H. Gu, ROMP and MCP as versatile and forceful tools to fabricate dendronized polymers for functional applications. Polym. Rev. 61(1), 1–53 (2021)

    Article  Google Scholar 

  17. Z. He, G. Wang, C. Wang, L. Guo, R. Wei, G. Song, D. Pan, R. Das, N. Naik, Z. Hu, Z. Guo, Overview of anion exchange membranes based on ring opening metathesis polymerization (ROMP). Polym. Rev. 61, 689–713 (2021)

    Article  CAS  Google Scholar 

  18. B.M. Novak, W. Risse, R.H. Grubbs, The development of well-defined catalysts for ring-opening olefin metathesis polymerizations (ROMP). Adv. Polym. Sci. 102, 47–72 (1992)

    Article  CAS  Google Scholar 

  19. A.A. W., M.N. G., U.S. Patent, 1955.

  20. J. Pribyl, K.B. Wagener, G. Rojas, ADMET polymers: synthesis, structure elucidation, and function. Mater. Chem. Front. 5(1), 14–43 (2021)

    Article  CAS  Google Scholar 

  21. T.W. Baughman, K.B. Wagener, recent advances in ADMET polymerization, in: M.R. Buchmeiser (Ed.), Metathesis Polymerization, pp. 1–42 (2005)

  22. Y. Sha, Z. Shen, H. Jia, Z. Luo, Main-chain ferrocene-containing polymers prepared by acyclic diene metathesis polymerization: a review. Curr. Org. Chem. 24(9), 1010–1017 (2020)

    Article  CAS  Google Scholar 

  23. L.C. da Silva, G. Rojas, M.D. Schulz, K.B. Wagener, Acyclic diene metathesis polymerization: History, methods and applications. Prog. Polym. Sci. 69, 79–107 (2017)

    Article  Google Scholar 

  24. E.A. Zuech, W.B. Hughes, D.H. Kubicek, E.T. Kittleman, Homogeneous catalysts for olefin disproportionations from nitrosyl molybdenum and tungsten compounds. J. Am. Chem. Soc. 92(3), 528–531 (1970)

    Article  CAS  Google Scholar 

  25. L. Caire da Silva, G. Rojas, M.D. Schulz, K.B. Wagener, Acyclic diene metathesis polymerization: History, methods and applications. Prog. Polym. Sci. 69, 79–107 (2017)

    Article  CAS  Google Scholar 

  26. M.D. Schulz, K.B. Wagener, Precision Polymers through ADMET Polymerization. Macromol. Chem. Phys. 215(20), 1936–1945 (2014)

    Article  CAS  Google Scholar 

  27. E.B. Berda, K.B. Wagener, Advances in acyclic diene metathesis polymerization. Polym Sci 5, 195–216 (2012)

    CAS  Google Scholar 

  28. K.L. Opper, K.B. Wagener, ADMET: metathesis polycondensation. J. Polym. Sci. Part A 49(4), 821–831 (2011)

    Article  CAS  Google Scholar 

  29. T.W. Baughman, K.B. Wagener, Recent advances in ADMET polymerization. Adv. Polym. Sci. 176, 1–42 (2005)

    Article  CAS  Google Scholar 

  30. H. Mutlu, L.M. de Espinosa, M.A.R. Meier, Acyclic diene metathesis: a versatile tool for the construction of defined polymer architectures. Chem. Soc. Rev. 40(3), 1404–1445 (2011)

    Article  CAS  PubMed  Google Scholar 

  31. T.W. Gaines, K.R. Williams, K.B. Wagener, G. Rojas, Microwave-assisted ADMET polymerization. Tetrahedron Lett. 56(25), 3923–3927 (2015)

    Article  CAS  Google Scholar 

  32. N.F. Sauty, L. Caire da Silva, C. Gallagher, R. Graf, K.B. Wagener, Unveiling the hyperbolic thermal behaviour of poly(p-phenylene alkylene)s. Polym. Chem. 6(33), 6073–6082 (2015)

    Article  CAS  Google Scholar 

  33. P.A. Delgado, D.Y. Liu, Z. Kean, K.B. Wagener, Synthesis of Poly(3-dodecyl-2,5-thienylene vinylene) by solid-state metathesis polycondensation. Macromolecules 44(24), 9529–9532 (2011)

    Article  CAS  Google Scholar 

  34. G.W. Oakley, S.E. Lehman, J.A. Smith, P. van Gerven, K.B. Wagener, Solid-state metathesis polycondensation. Macromolecules 36(3), 539–542 (2003)

    Article  CAS  Google Scholar 

  35. H. Weychardt, H. Plenio, acyclic diene metathesis polymerization of divinylarenes and divinylferrocenes with grubbs-type olefin metathesis catalysts. Organometallics 27(7), 1479–1485 (2008)

    Article  CAS  Google Scholar 

  36. T. Lebarbe, A.S. More, P.S. Sane, E. Grau, C. Alfos, H. Cramail, Bio-based aliphatic polyurethanes through ADMET polymerization in bulk and green solvent. Macromol. Rapid Commun. 35(4), 479–483 (2014)

    Article  CAS  PubMed  Google Scholar 

  37. M.B. Canalp, W.H. Binder, Hybrid polymers bearing oligo-l-lysine(carboxybenzyl)s: synthesis and investigations of secondary structure. RSC Adv. 10(3), 1287–1295 (2020)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  38. Y. Sha, H. Jia, Z. Shen, Z. Luo, Synthetic strategies, properties, and applications of unsaturated main-chain metallopolymers prepared by olefin metathesis polymerization. Polym. Rev. 15, 1–41 (2020)

    Google Scholar 

  39. F.C. Courchay, J.C. Sworen, I. Ghiviriga, K.A. Abboud, K.B. Wagener, Understanding structural isomerization during ruthenium-catalyzed olefin metathesis: A deuterium labeling study. Organometallics 25(26), 6074–6086 (2006)

    Article  CAS  Google Scholar 

  40. P.A. Fokou, M.A. Meier, Studying and suppressing olefin isomerization side reactions during ADMET polymerizations. Macromol. Rapid Commun. 31(4), 368–373 (2010)

    Article  CAS  PubMed  Google Scholar 

  41. M. Bell, H.G. Hester, A.N. Gallman, V. Gomez, J. Pribyl, G. Rojas, A. Riegger, T. Weil, H. Watanabe, Y. Chujo, K.B. Wagener, Bulk acyclic diene metathesis polycondensation. Macromol. Chem. Phys. 220(15), 1900223 (2019)

    Article  Google Scholar 

  42. S. Karabulut, C. Aydogdu, B. Düz, Y. İmamoglu, Metal-containing polymers synthesized via acyclic diene metathesis (ADMET) polymerization using electrochemically-reduced tungsten-based catalyst: Polycarbosilanes. J. Inorg. Organomet. Polym. Mater. 17(3), 517–523 (2007)

    Article  CAS  Google Scholar 

  43. W.J. Wolf, J. Li, S.C. Jones, B.M. Stoltz, R.H. Grubbs, Efficient synthesis of geminal-dialkyl dienes for olefin metathesis polymerization. Macromolecules 53(18), 7803–7809 (2020)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  44. J.M.B.K.B.W.J.T. Patton, Acyclic diene metathesis (ADMET) polymerization. Synth Unsaturated Polyesters. Macromol 25, 3862–3867 (1992)

    CAS  Google Scholar 

  45. K.B. Wagener, K. Brzezinska, Acyclic diene metathesis (ADMET) polymerization: synthesis of unsaturated polyethers. Macromolecules 24(19), 5273–5277 (1991)

    Article  CAS  Google Scholar 

  46. K.B. Wagener, D.W. Smith, Acyclic diene metathesis polymerization: synthesis and characterization of unsaturated poly[carbo(dimethyl)silanes]. Macromolecules 24(23), 6073–6078 (1991)

    Article  CAS  Google Scholar 

  47. Y. Chai, Q. Chen, C. Huang, Q. Zheng, M. North, H. Xie, Introducing the reversible chemistry of CO2 with diols mediated by organic superbases into polycarbonate synthesis. Green Chem. 22(15), 4871–4877 (2020)

    Article  CAS  Google Scholar 

  48. L. Montero de Espinosa, M.A. Meier, Synthesis of star- and block-copolymers using ADMET: head-to-tail selectivity during step-growth polymerization. Chem. Commun. 47(6), 1908–1910 (2011)

    Article  CAS  Google Scholar 

  49. D. Butilkov, N.G. Lemcoff, Jojoba oil olefin metathesis: a valuable source for bio-renewable materials. Green Chem. 16(11), 4728–4733 (2014)

    Article  CAS  Google Scholar 

  50. B.R. Moser, K.E. Vermillion, B.N. Banks, K.M. Doll, Renewable aliphatic polyesters from fatty dienes by acyclic diene metathesis polycondensation. J. Am. Oil Chem. Soc. 97, 517–530 (2020)

    Article  CAS  Google Scholar 

  51. D. Le, C. Samart, S. Kongparakul, K. Nomura, Synthesis of new polyesters by acyclic diene metathesis polymerization of bio-based α, ω-dienes prepared from eugenol and castor oil (undecenoate). RSC Adv. 9(18), 10245–10252 (2019)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  52. A. Lv, Y. Cui, F.-S. Du, Z.-C. Li, Thermally degradable polyesters with tunable degradation temperatures via postpolymerization modification and intramolecular cyclization. Macromolecules 49(22), 8449–8458 (2016)

    Article  CAS  Google Scholar 

  53. T.W. Gaines, T. Nakano, Y. Chujo, E.B. Trigg, K.I. Winey, K.B. Wagener, Precise sulfite functionalization of polyolefins via ADMET polymerization. ACS Macro Lett. 4(6), 624–627 (2015)

    Article  CAS  PubMed  Google Scholar 

  54. A. Cankaya, M. Steinmann, Y. Bülbül, I. Lieberwirth, F.R. Wurm, Side-chain poly(phosphoramidate)s via acyclic diene metathesis polycondensation. Polym. Chem. 7(31), 5004–5010 (2016)

    Article  CAS  Google Scholar 

  55. T. Haider, O. Suraeva, M.L. O’Duill, J. Mars, M. Mezger, I. Lieberwirth, F.R. Wurm, Controlling the crystal structure of precisely spaced polyethylene-like polyphosphoesters. Polym. Chem. 11(20), 3404–3415 (2020)

    Article  CAS  Google Scholar 

  56. C. Simocko, T.C. Young, K.B. Wagener, ADMET polymers containing precisely spaced pendant boronic acids and esters. Macromolecules 48(16), 5470–5473 (2015)

    Article  CAS  Google Scholar 

  57. I. Kawarazaki, A. Takasu, Synthesis of unsaturated nonionic poly(ester-sulfones) via acyclic diene metathesis (ADMET) polymerization and anode-selective electrophoretic deposition. Macromol. Chem. Phys. 217(23), 2595–2600 (2016)

    Article  CAS  Google Scholar 

  58. T.W. Gaines, E.B. Trigg, K.I. Winey, K.B. Wagener, High melting precision sulfone polyethylenes synthesized by ADMET chemistry. Macromol. Chem. Phys. 217(21), 2351–2359 (2016)

    Article  CAS  Google Scholar 

  59. K. Nomura, P. Chaijaroen, M.M. Abdellatif, Synthesis of biobased long-chain polyesters by acyclic diene metathesis polymerization and tandem hydrogenation and depolymerization with ethylene. ACS Omega 5(29), 18301–18312 (2020)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  60. L. Montero de Espinosa, M.A.R. Meier, Plant oils: The perfect renewable resource for polymer science?! Eur. Polym. J. 47(5), 837–852 (2011)

    Article  CAS  Google Scholar 

  61. I. Barbara, A.L. Flourat, F. Allais, Renewable polymers derived from ferulic acid and biobased diols via ADMET. Eur. Polym. J. 62, 236–243 (2015)

    Article  CAS  Google Scholar 

  62. L. Hollande, A.S. Jaufurally, P.-H. Ducrot, F. Allais, ADMET polymerization of biobased monomers deriving from syringaresinol. RSC Adv. 6(50), 44297–44304 (2016)

    Article  CAS  Google Scholar 

  63. T. Ren, Q. Chen, C. Zhao, Q. Zheng, H. Xie, M. North, Introducing the Tishchenko reaction into sustainable polymer chemistry. Green Chem. 22(5), 1542–1547 (2020)

    Article  CAS  Google Scholar 

  64. M. Piccini, D.J. Leak, C.J. Chuck, A. Buchard, Polymers from sugars and unsaturated fatty acids: ADMET polymerisation of monomers derived from d-xylose, d-mannose and castor oil. Polym. Chem. 11, 2681–2691 (2020)

    Article  CAS  Google Scholar 

  65. M. Piccini, J. Lightfoot, B.C. Dominguez, A. Buchard, Xylose-Based polyethers and polyesters via ADMET polymerization toward polyethylene-like materials. ACS Appl. Polym. Mater. 3, 5870–5881 (2021)

    Article  CAS  Google Scholar 

  66. S. Luleburgaz, M. Abuaf, U. Tunca, G. Hizal, H. Durmaz, Synthesis of Poly(vitamin C) through ADMET. Macromol. Rapid Commun. 38(11), 15 (2017)

    Article  Google Scholar 

  67. J. Freudenberg, W.H. Binder, Multisegmented hybrid polymer based on oligo-amino acids: synthesis and secondary structure in solution and in the solid state. Macromolecules 52(12), 4534–4544 (2019)

    Article  CAS  Google Scholar 

  68. J. Freudenberg, S. Poppe, W.H. Binder, Precision polymers containing main-chain-amino acids: ADMET polymerization and crystallization. RSC Adv. 7(75), 47507–47519 (2017)

    Article  CAS  Google Scholar 

  69. E.G.G. Hibert, D. Pintori, S. Lecommandoux, H. Cramail, ADMET polymerization of α, ω-unsaturated glycolipids: synthesis and physico-chemical properties of the resulting polymers. Polym. Chem. 8, 3731–3739 (2019)

    Article  Google Scholar 

  70. W. Song, Y. You, T.-J. Li, J. Li, L. Ding, Perylene bisimide in-chain polyethylene with unique self-assembly nanostructure through acyclic diene metathesis (ADMET) polymerization. Chin. J. Polym. Sci. 36(6), 703–711 (2018)

    Article  CAS  Google Scholar 

  71. P.K. Dannecker, U. Biermann, A. Sink, F.R. Bloesser, J.O. Metzger, M.A.R. Meier, Fatty acid-derived aliphatic long chain polyethers by a combination of catalytic ester reduction and ADMET or thiol-ene polymerization. Macromol. Chem. Phys. 220, 1800440 (2018)

    Article  Google Scholar 

  72. D.M. Pesko, M.A. Webb, Y. Jung, Q. Zheng, T.F. Miller, G.W. Coates, N.P. Balsara, Universal relationship between conductivity and solvation-site connectivity in ether-based polymer electrolytes. Macromolecules 49(14), 5244–5255 (2016)

    Article  CAS  Google Scholar 

  73. K.A. Miller, E.G. Morado, S.R. Samanta, B.A. Walker, A.Z. Nelson, S. Sen, D.T. Tran, D.J. Whitaker, R.H. Ewoldt, P.V. Braun, S.C. Zimmerman, Acid-triggered, acid-generating, and self-amplifying degradable polymers. J. Am. Chem. Soc. 141(7), 2838–2842 (2019)

    Article  CAS  PubMed  Google Scholar 

  74. S. Song, W. Guo, S. Zou, Z. Fu, J. Xu, Z. Fan, Polyethylene containing aliphatic ring and aromatic ring defects in the main chain: Synthesis via ADMET and comparisons of thermal properties and crystalline structure. Polymer 107, 113–121 (2016)

    Article  CAS  Google Scholar 

  75. Y. Cao, G. Hu, S. Lin, G.L. Rempel, Q. Pan, Synthesis of precisely diphenyl ether-functionalized polyethylene via acyclic diene metathesis polymerization. Polymer 175, 41–48 (2019)

    Article  CAS  Google Scholar 

  76. L. Wang, M. Wang, L.-X. Guo, Y. Sun, X.-Q. Zhang, B.-P. Lin, H. Yang, Oligodeoxynucleosides with olefin bridges. Macromolecules 52(2), 649–659 (2018)

    Article  Google Scholar 

  77. L. Vlaminck, S. Lingier, A. Hufendiek, F.E. Du Prez, Lignin inspired phenolic polyethers synthesized via ADMET: Systematic structure-property investigation. Eur. Polym. J. 95, 503–513 (2017)

    Article  CAS  Google Scholar 

  78. Y. Suzuki, T. Sakamoto, M. Yoshio, T. Kato, Development of functional nanoporous membranes based on photocleavable columnar liquid crystals—selective adsorption of ionic dyes. Eur. Polym. J. 134, 109859 (2020)

    Article  CAS  Google Scholar 

  79. S.-F. Song, Y.-T. Guo, R.-Y. Wang, Z.-S. Fu, J.-T. Xu, Z.-Q. Fan, Synthesis and crystallization behavior of equisequential ADMET polyethylene containing arylene ether defects: remarkable effects of substitution position and arylene size. Macromolecules 49(16), 6001–6011 (2016)

    Article  CAS  Google Scholar 

  80. X. Liu, T. Chen, F. Yu, Y. Shang, X. Meng, Z.-R. Chen, AIE-active random conjugated copolymers synthesized by ADMET polymerization as a fluorescent probe specific for palladium detection. Macromolecules 53(4), 1224–1232 (2020)

    Article  CAS  Google Scholar 

  81. N. Hu, C.K. Mai, G.H. Fredrickson, G.C. Bazan, One-pot synthesis of semicrystalline/amorphous multiblock copolymers via divinyl-terminated telechelic polyolefins. Chem. Commun. 52(11), 2237–2240 (2016)

    Article  CAS  Google Scholar 

  82. B. Zhang, C. He, X. Chen, Z. Tian, F. Li, The synergistic effect of polyamidoamine dendrimers and sodium silicate on the corrosion of carbon steel in soft water. Corros. Sci. 90, 585–596 (2015)

    Article  CAS  Google Scholar 

  83. F.-R. Zeng, Q.-L. Zhu, Z.-L. Li, Sequential modification of ADMET polyketone via oxime chemistry and electrophilic alkoxyetherification. Aust. J. Chem. 71(6), 449–454 (2018)

    Article  CAS  Google Scholar 

  84. E.B. Trigg, B.J. Tiegs, G.W. Coates, K.I. Winey, High morphological order in a nearly precise acid-containing polymer and ionomer. ACS Macro Lett. 6(9), 947–951 (2017)

    Article  CAS  PubMed  Google Scholar 

  85. C.D.C. Travis, W. Baughman, K.I. Winey, K.B. Wagener, Synthesis and morphology of well-defined poly(ethylene-co-acrylic acid). Copolym. Macromol. 40(18), 6564–6571 (2007)

    Article  Google Scholar 

  86. T.W. Gaines, M.H. Bell, E.B. Trigg, K.I. Winey, K.B. Wagener, Precision sulfonic acid polyolefins via heterogenous to homogenous deprotection. Macromol. Chem. Phys. 219(11), 1700634 (2018)

    Article  Google Scholar 

  87. O. Kreye, T. Tóth, M.A.R. Meier, Poly-α, β-unsaturated aldehydes derived from castor oil via ADMET polymerization. Eur. J. Lipid Sci. Tech. 113(1), 31–38 (2011)

    Article  CAS  Google Scholar 

  88. E. Boz, K.B. Wagener, A. Ghosal, R. Fu, R.G. Alamo, Synthesis and crystallization of precision ADMET polyolefins containing halogens. Macromolecules 39(13), 4437–4447 (2006)

    Article  CAS  Google Scholar 

  89. K.B.W.E. Boz, Synthesis and crystallization of precision ADMET polyolefins containing halogens. Macromolecules 39, 4437–4447 (2006)

    Article  CAS  Google Scholar 

  90. A. Morontsev, M. Gringolts, V. Lakhtin, E. Finkelshtein, Synthesis of high-molecular weight poly(1,1-dimethyl-1-silapentene) by olefin metathesis polymerization in the presence of Grubbs catalysts. J. Organomet. Chem. 911, 121156 (2020)

    Article  Google Scholar 

  91. B.S. Aitken, M. Lee, M.T. Hunley, H.W. Gibson, K.B. Wagener, Synthesis of precision ionic polyolefins derived from ionic liquids. Macromolecules 43(4), 1699–1701 (2010)

    Article  CAS  Google Scholar 

  92. J. Friebel, C.P. Ender, M. Mezger, J. Michels, M. Wagner, K.B. Wagener, T. Weil, Synthesis of precision poly(1,3-adamantylene alkylene)s via acyclic diene metathesis polycondensation. Macromolecules 52(12), 4483–4491 (2019)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  93. P. Żak, M. Majchrzak, G. Wilkowski, B. Dudziec, M. Dutkiewicz, B. Marciniec, Synthesis and characterization of functionalized molecular and macromolecular double-decker silsesquioxane systems. RSC Adv. 6(12), 10054–10063 (2016)

    Article  Google Scholar 

  94. P. Żak, D. Frąckowiak, M. Grzelak, M. Bołt, M. Kubicki, B. Marciniec, Olefin Metathesis of vinylgermanium derivatives as method for the synthesis of functionalized cubic and double-decker germasilsesquioxanes. Adv. Synth. Catal. 358(20), 3265–3276 (2016)

    Article  Google Scholar 

  95. P. Zak, C. Pietraszuk, Application of olefin metathesis in the synthesis of functionalized polyhedral oligomeric silsesquioxanes (POSS) and POSS-containing polymeric materials. Beilstein J. Org. Chem. 15, 310–332 (2019)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  96. N. Ren, X. Zhu, Synthesis of hyperbranched polyolefins and polyethylenes via ADMET of monomers bearing non-selective olefins. Polym. Chem. 10(45), 6174–6182 (2019)

    Article  CAS  Google Scholar 

  97. U.H. Bunz, D. Maker, M. Porz, Alkene metathesis - a tool for the synthesis of conjugated polymers. Macromol. Rapid Commun. 33(10), 886–910 (2012)

    Article  CAS  PubMed  Google Scholar 

  98. M.A.-H. Michael, G. Organ, S. Avola, N. Hadei, C.J.O.B.J. Nasielski, C. Valente, Biaryls made easy: PEPPSI and the Kumada–Tamao–Corriu reaction. Chem. Eur. J 13, 150–157 (2007)

    Article  Google Scholar 

  99. U.H.F.B.S. Setayesh, Synthesis of cymantrene-containing organometallic polymers using the suzuki coupling. Organometallics 15, 5470 (1996)

    Article  CAS  Google Scholar 

  100. S.M.W. James, N. Wilson, U.H.F.B.K. McAlpine, Acetylene gas: a reagent in the synthesis of high molecular weight poly(p-phenyleneethynylene)s utilizing very low catalyst loadings. Macromolecules 35, 3799 (2002)

    Article  Google Scholar 

  101. G.C. Fu, The development of versatile methods for palladium-catalyzed coupling reactions of aryl electrophiles through the use of P(t-Bu)3 and PCy3 as ligands. Acc. Chem. Res. 41, 1555 (2008)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  102. A.M.N. Blouin, M. Leclerc, A low-bandgap poly(2,7-Carbazole) derivative for use in high-performance solar cells. Adv. Mater. 19, 2295 (2007)

    Article  CAS  Google Scholar 

  103. W. Joo, C.W. Bielawski, Design, synthesis and study of a photochromic alpha, omega-diene: toward new classes of photoswitchable polymers. Org. Biomol. Chem. 17(9), 2486–2491 (2019)

    Article  CAS  PubMed  Google Scholar 

  104. J.C. Speros, B.D. Paulsen, B.S. Slowinski, C.D. Frisbie, M.A. Hillmyer, Band gap and HOMO level control in poly(thienylene vinylene)s prepared by ADMET polymerization. ACS Macro Lett. 1(8), 986–990 (2012)

    Article  CAS  PubMed  Google Scholar 

  105. Z. Zhang, Y. Qin, Synthesis and characterization of poly(selenylene vinylene) and poly(selenylene vinylene)-co-poly(thienylene vinylene) through acyclic diene metathesis (ADMET) polymerization. ACS Macro Lett. 4(7), 679–683 (2015)

    Article  CAS  PubMed  Google Scholar 

  106. Z. Zhang, Y. Qin, Structurally diverse poly(thienylene vinylene)s (PTVs) with systematically tunable properties through acyclic diene metathesis (ADMET) and postpolymerization modification. Macromolecules 49(9), 3318–3327 (2016)

    Article  CAS  Google Scholar 

  107. T. Miyashita, K. Nomura, Catalytic one-pot synthesis of end-functionalized poly(9,9′-di-n-octylfluorenevinylene)s by acyclic diene metathesis (ADMET) polymerization using ruthenium-carbene catalysts. Macromolecules 49(2), 518–526 (2016)

    Article  CAS  Google Scholar 

  108. T. Miyashita, M. Kunisawa, S. Sueki, K. Nomura, Synthesis of poly(arylene vinylene)s with different end groups by combining acyclic diene metathesis polymerization with wittig-type couplings. Angew. Chem. Int. Ed. 56(19), 5288–5293 (2017)

    Article  CAS  Google Scholar 

  109. J.T. Offenloch, J. Willenbacher, P. Tzvetkova, C. Heiler, H. Mutlu, C. Barner-Kowollik, Degradable fluorescent single-chain nanoparticles based on metathesis polymers. Chem. Commun. 53(4), 775–778 (2017)

    Article  CAS  Google Scholar 

  110. H. Mutlu, C. Barner-Kowollik, Green chain-shattering polymers based on a self-immolative azobenzene motif. Polym. Chem. 7(12), 2272–2279 (2016)

    Article  CAS  Google Scholar 

  111. C. Appiah, G. Woltersdorf, W.H. Binder, Synthesis of photoresponsive main-chain oligomers with azobenzene moieties via ADMET oligomerization and their micellization properties. Polym. Chem. 8(18), 2752–2763 (2017)

    Article  CAS  Google Scholar 

  112. L. Ding, M. Xu, J. Wang, Y. Liao, J. Qiu, Controlled synthesis of azobenzene functionalized homo and copolymers via direct acyclic diene metathesis polymerization. Polymer 55(7), 1681–1687 (2014)

    Article  CAS  Google Scholar 

  113. L. Ding, J. Li, T. Li, L. Zhang, W. Song, Linear, Y-shaped, and H-shaped amphiphilic azobenzene copolymers: Facile synthesis and topological effect on self-assembly and photoresponsive property. React. Funct. Polym. 121, 15–22 (2017)

    Article  CAS  Google Scholar 

  114. L. Liu, M. Wang, L.-X. Guo, Y. Sun, X.-Q. Zhang, B.-P. Lin, H. Yang, Aggregation-induced emission luminogen-functionalized liquid crystal elastomer soft actuators. Macromolecules 51(12), 4516–4524 (2018)

    Article  CAS  Google Scholar 

  115. H.A.G. Singh, R.M. Peetz, Studies on homologous random and alternating segmented conjugated polymers with and without silicon synthesized by ADMET. Polym. Chem. 7, 669–679 (2016)

    Article  CAS  Google Scholar 

  116. H.P.H. Weychardt, Acyclic diene metathesis polymerization of divinylarenes and divinylferrocenes with grubbs-type olefin metathesis catalysts. Organometallics 27, 1479–1485 (2008)

    Article  CAS  Google Scholar 

  117. L. Greb, H. Mutlu, C. Barner-Kowollik, J.-M. Lehn, Photo- and metallo-responsive N-Alkyl α-bisimines as orthogonally addressable main-chain functional groups in metathesis polymers. J. Am. Chem. Soc. 138(4), 1142–1145 (2016)

    Article  CAS  PubMed  Google Scholar 

  118. L. Ding, J. Qiu, J. Li, C. Wang, L. Wang, Novel Photoresponsive linear, graft, and comb-like copolymers with azobenzene chromophores in the main-chain and/or side-chain: facile one-pot synthesis and photoresponse properties. Macromol. Rapid Commun. 36(17), 1578–1584 (2015)

    Article  CAS  PubMed  Google Scholar 

  119. L. Ding, W. Song, R. Jiang, L. Zhu, Macrocycle-based topological azo-polymers: facile synthesis and unusual photoresponsive properties. Polym. Chem. 8(46), 7133–7142 (2017)

    Article  CAS  Google Scholar 

  120. G. Singh, H. Ardolic, R.M. Peetz, Studies on homologous random and alternating segmented conjugated polymers with and without silicon synthesized by ADMET. Polym. Chem. 7, 669–679 (2016)

    Article  CAS  Google Scholar 

  121. R.G. Chaudhary, H.D. Juneja, R. Pagadala, N.V. Gandhare, M.P. Gharpure, Synthesis, characterisation and thermal degradation behaviour of some coordination polymers by using TG–DTG and DTA techniques. J. Saudi Chem. Soc. 19(4), 442–453 (2015)

    Article  Google Scholar 

  122. R.G. Chaudhary, P. Ali, N.V. Gandhare, J.A. Tanna, H.D. Juneja, Thermal decomposition kinetics of some transition metal coordination polymers of fumaroyl bis (paramethoxyphenylcarbamide) using DTG/DTA techniques. Arab. J. Chem. 12(7), 1070–1082 (2019)

    Article  CAS  Google Scholar 

  123. R. Bagade, R.G. Chaudhary, A. Potbhare, A. Mondal, M. Desimone, K. Dadure, R. Mishra, H. Juneja, Microspheres/custard-apples copper (II) chelate polymer: characterization. Dock. Antioxid. Antibact. Assay Chem. Select 4(20), 6233–6244 (2019)

    CAS  Google Scholar 

  124. R. Bagade, V. Sonkusare, A.K. Potbhare, R.G. Chaudhary, R. Husain, H.D. Juneja, Fabrication of microflower-shaped mesoporous Fe (II) chelate polymer for photocatalytic performance under visible light. Mater. Today 15, 566–574 (2019)

    CAS  Google Scholar 

  125. C.G. Hardy, J. Zhang, Y. Yan, L. Ren, C. Tang, Metallopolymers with transition metals in the side-chain by living and controlled polymerization techniques. Prog. Polym. Sci. 39(10), 1742–1796 (2014)

    Article  CAS  Google Scholar 

  126. Y. Yan, J. Zhang, L. Ren, C. Tang, Metal-containing and related polymers for biomedical applications. Chem. Soc. Rev. 45(19), 5232–5263 (2016)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  127. T. Zhu, Y. Sha, J. Yan, P. Pageni, M.A. Rahman, Y. Yan, C. Tang, Metallo-polyelectrolytes as a class of ionic macromolecules for functional materials. Nat. Commun. 9(1), 4329 (2018)

    Article  PubMed  PubMed Central  Google Scholar 

  128. Y. Yan, P. Pageni, M.P. Kabir, C.B. Tang, Metallocenium chemistry and its emerging impact on synthetic macromolecular chemistry. Synlett 27(7), 984–1005 (2016)

    Article  CAS  Google Scholar 

  129. J.T.P. Alan, S. Gamble, J.M. Boncella, Acyclic diene metathesis polymerizations of ferrocene monomers. Makromol. Chem. Rapid Commun. 13, 109–115 (1993)

    Google Scholar 

  130. A. Hildebrandt, K. Al-Khalyfeh, J.F. Nawroth, R. Jordan, Electron transfer studies on conjugated ferrocenyl-containing oligomers. Organometallics 35(21), 3713–3719 (2016)

    Article  CAS  Google Scholar 

  131. H. Zhang, F. Liu, J. Cao, L. Ling, R.-F. Sun, Ferrocene-containing polymers synthesized by acyclic diene metathesis (ADMET) polymerization. Chin. J. Polym. Sci. 34(2), 242–252 (2015)

    Article  Google Scholar 

  132. X. Gao, L. Deng, J. Hu, H. Zhang, Ferrocene-containing conjugated oligomers synthesized by acyclic diene metathesis polymerization. Polymers (Basel) 11(8), 15 (2019)

    Article  Google Scholar 

  133. B.L. Dewing, N.G. Bible, C.J. Ellison, M.K. Mahanthappa, Electrochemically stable, high transference number lithium bis(malonato)borate polymer solution electrolytes. Chem. Mater. 32(9), 3794–3804 (2020)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We would like to acknowledge the support by the NSFC (No. 21975205, 21504068), Natural Science Foundation of Chongqing (cstc2020jcyj-msxmX1078), Shaanxi National Science Foundation (2020JM-138), Fundamental Research Funds for the Central Universities (3102017jc01001), and Open Project of State Key Laboratory of Supramolecular Structure and Materials (sklssm2022022).

Funding

The authors have not disclosed any funding.

Author information

Authors and Affiliations

  1. Chongqing Technology Innovation Centre, Northwestern Polytechnical University, Chongqing, 401135, People’s Republic of China

    Shuang Liu, Jing Yan & Yi Yan

  2. Key Laboratory of Special Functional and Smart Polymer Materials of Ministry of Industry and Information Technology, Department of Chemistry, School of Chemistry and Chemical Engineering, Northwestern Polytechnical University, Xi’an, 710129, People’s Republic of China

    Shuang Liu, Jing Yan, Qiuyu Zhang & Yi Yan

Authors
  1. Shuang Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jing Yan
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Qiuyu Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Yi Yan
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Jing Yan or Yi Yan.

Ethics declarations

Conflict of interest

There are no conflicts to declare.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Liu, S., Yan, J., Zhang, Q. et al. Acyclic Diene Metathesis (ADMET) as Powerful Tool for Functional Polymers with Versatile Architectures. J Inorg Organomet Polym 32, 3368–3394 (2022). https://doi.org/10.1007/s10904-022-02386-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10904-022-02386-x

Keywords

Search

Navigation