Register      Login
Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Synthesis of Novel Triazole-Containing Phosphonate Polymers

Ciarán Dolan A B D , Briar Naysmith A D , Simon F. R. Hinkley C , Ian M. Sims C , Margaret A. Brimble A B , David E. Williams A B and Jianyong Jin A B E
+ Author Affiliations
- Author Affiliations

A School of Chemical Sciences, University of Auckland, Private Bag 92019, Auckland 1142, New Zealand.

B The MacDiarmid Institute for Advanced Materials and Nanotechnology, Victoria University of Wellington, PO Box 600, Wellington 6140, New Zealand.

C The Ferrier Research Institute, Victoria University of Wellington, PO Box 33436, Petone 5046, New Zealand.

D Both authors have contributed equally to this work.

E Corresponding author. Email: j.jin@auckland.ac.nz

Australian Journal of Chemistry 68(4) 680-686 https://doi.org/10.1071/CH14513
Submitted: 22 August 2014  Accepted: 5 January 2015   Published: 28 January 2015

Abstract

The objective of this research was to develop novel phosphonate-containing polymers as they remain a relatively under researched area of polymer chemistry. Herein, we report the synthesis and characterization of 2-(1-(2-(diethoxyphosphoryl)ethyl)-1H-1,2,3-triazol-4-yl)ethyl acrylate (M1) and diethyl (2-(4-(2-acrylamidoethyl)-1H-1,2,3-triazol-1-yl)ethyl)phosphonate (M2) monomers using the copper-catalyzed azide–alkyne cycloaddition (CuAAC) ‘click’ reaction, and their subsequent polymerization via both uncontrolled and reversible addition–fragmentation chain transfer (RAFT) polymerization techniques yielding phosphonate polymers (P1P4).


References

[1]  A. Graillot, S. Monge, C. Faur, D. Bouyer, J.-J. Robin, Polym. Chem. 2013, 4, 795.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXjtl2nsQ%3D%3D&md5=826b19b4695b603c933dad902a105a95CAS |

[2]  H. Gali, K. R. Prabhu, S. R. Karra, K. V. Katti, J. Org. Chem. 2000, 65, 676.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXksVSktg%3D%3D&md5=be01290b3d9a0a1e37edc0b0e33b836dCAS |

[3]  A. Z. Albayrak, D. Avci, Des. Monomers Polym. 2004, 7, 291.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXltlGntrc%3D&md5=b5dfbeb36a058ce4c07811dbc3aa82c9CAS |

[4]  L. C. Porto, K. Aissou, C. Giacomelli, T. Baron, C. Rochas, I. Pignot-Paintrand, S. P. Armes, A. L. Lewis, V. Soldi, R. Borsali, Macromolecules 2011, 44, 2240.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXis1aksLY%3D&md5=ea4d0be55b5e5a30322fb747922b6a84CAS |

[5]  K. Kossev, A. Vassilev, Y. Popova, I. Ivanov, K. Troev, Polymer 2003, 44, 1987.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXhsF2gsL0%3D&md5=56e5ab605a9a949907d7f60485f6b2afCAS |

[6]  W.-J. Shu, L.-H. Perng, W.-K. Chin, Polym. J. 2001, 33, 676.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXntVGktrs%3D&md5=a591ec33d17bed1ad3e80558b4030c36CAS |

[7]  I. Yakovlev, T. J. Deming, ACS Macro Lett. 2014, 3, 378.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXlsFymsb8%3D&md5=01f512c2fa9e0a37949abfdaac701680CAS |

[8]  J. D. Goff, P. P. Huffstetler, W. C. Miles, N. Pothayee, C. M. Reinholz, S. Ball, R. M. Davis, J. S. Riffle, Chem. Mater. 2009, 21, 4784.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXht1SnsbnK&md5=246b108ed0009169a890f1bd0b6b0399CAS |

[9]  A. Clearfield, Curr. Opin. Solid State Mater. Sci. 1996, 1, 268.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK28XksF2isbw%3D&md5=2ead73f4439c456ed293b219c63f57cbCAS |

[10]  B. Zhang, L. Zhang, F. Li, W. Hu, P. M. Hannam, Corros. Sci. 2010, 52, 3883.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXht1Onu7fN&md5=2e45fa489e339a77cf5d277a5b262ca8CAS |

[11]  E. Brunet, O. Juanes, L. Jiménez, J. C. Rodríguez-Ubis, Tetrahedron Lett. 2009, 50, 5361.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXps1equ7w%3D&md5=a1a284170cff8b67fadce6cf2988a7f2CAS |

[12]  G. David, C. Negrell-Guirao, F. Iftene, B. Boutevin, K. Chougrani, Polym. Chem. 2012, 3, 265.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XntlemtQ%3D%3D&md5=4cb4bf8b3a3d6a6f578bf9d6dc5eb80aCAS |

[13]  J. E. Klee, U. Lehmann, Beilstein J. Org. Chem. 2009, 5, 72.
         | Crossref | GoogleScholarGoogle Scholar | 20300456PubMed |

[14]  Y. Catel, M. Degrange, L. L. E. Pluart, P.-J. Madec, T.-N. Pham, L. Picton, J. Polym. Sci., Part A: Polym. Chem. 2008, 46, 7074.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhsVSnur7L&md5=6d9642dd936b77f514875c67bb285fd3CAS |

[15]  Y. Shen, Y. Ma, Z. Li, J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 708.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38Xhs1KlsrnI&md5=77ab9b080c575182e07ccb0e60ccd12aCAS |

[16]  G. Moad, E. Rizzardo, S. H. Thang, Aust. J. Chem. 2009, 62, 1402.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhsVers7bN&md5=1ef863345e7f95a5bdf8bc850dae9e0eCAS |

[17]  J. B. McLeary, M. P. Tonge, B. Klumperman, Macromol. Rapid Commun. 2006, 27, 1233.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XosVelsL0%3D&md5=8363379dea1ba41a54164b7a1194f78bCAS |

[18]  A. Vega-Rios, A. Licea-Claveríe, J. Mex. Chem. Soc. 2011, 55, 21.
         | 1:CAS:528:DC%2BC3MXpt1ynsrs%3D&md5=7f071aaa2ec9069956a46ce5e4008d9fCAS |

[19]  A. Sebenik, Prog. Polym. Sci. 1998, 23, 875.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXks1Glsbo%3D&md5=4f126dc1d586cf7478eb672265247b13CAS |

[20]  A. Popa, C.-M. Davidescu, P. Negrea, G. Ilia, A. Katsaros, K. D. Demadis, Ind. Eng. Chem. Res. 2008, 47, 2010.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXitFehsb0%3D&md5=c13fb44ea015ca61bf456d2d7b602a3dCAS |

[21]  D. Avci, A.-Z. Albayrak, J. Polym. Sci., Part A: Polym. Chem. 2003, 41, 2207.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXmtlyjtLs%3D&md5=96ad9ef0a0967103fcff8b328776b656CAS |

[22]  I. Cabasso, J. Smid, S. K. Sahni, J. Appl. Polym. Sci. 1990, 41, 3025.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3MXot1KnsQ%3D%3D&md5=8fdf67cf3ef7db7593bad40e9f07b18aCAS |

[23]  K. Riedelsberger, W. Jaeger, A. Friedrich, Des. Monomers Polym. 2000, 3, 35.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXitVWksLg%3D&md5=09320e9130dc3a5ae9a1958fde97889dCAS |

[24]  C. Boyer, V. Bulmus, T. P. Davis, V. Ladmiral, J. Liu, S. Perrier, Chem. Rev. 2009, 109, 5402.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhtFCqtbvP&md5=95b0ee29d2f64b18cac50b04ed3a3700CAS | 19764725PubMed |

[25]  V. Mellon, D. Rinaldi, E. Bourgeat-Lami, F. D’Agosto, Macromolecules 2005, 38, 1591.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXhtFentb4%3D&md5=f5b2c3b7891957da7838c0f78538c293CAS |

[26]  S. H. Yang, D. J. Lee, M. A. Brimble, Org. Lett. 2011, 13, 5604.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXht1WksLzI&md5=b5ece2936c3cdfd2e551034f2ab67f58CAS | 21939187PubMed |