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Click chemisry

Click chemistry

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Click chemistry for functional polymers

Functional norbornenyl-based macromonomers and RAFT-synthesized thermosensitive polymers have been synthesized by CuAAC and controlled polymerizations (ROP and RAFT). Thermo-activated and photo-activated hydrothiolations including thiol-ene and thiol-yne perfomed on such macromonomers and polymers have been monitored to target well-defined mikto-arm polymers and telechelic polymers in one-pot processes. Decorated iron magnetic nanoparticles with functional hydrophile ligands leading to core-shell nanoparticles have been employed to target hybrid nanoparticles for hyperthermia drug release and reversible magneto-sensitive hydrogels via Diels-Alder reactions.

 

  Researchers

  • Véronique Montembault
  • Sandie Piogé
  • Sagrario Pascual
  • Laurent Fontaine
  • Florent Calvayrac
  • Lazhar Benyahia

Related papers

  • T. T. N'Guyen, K. Oussadi, V. Montembault, L. Fontaine, J. Polym. Sci., A: Polym. Chem. 2013, 51, 415-423.
  • T. T. N’Guyen, H. T. T. Duong, J. Basuki, V. Montembault, S. Pascual, C. Guibert, J. Fresnais, C. Boyer, M. R. Whittaker, T. P. Davis, L. Fontaine, Angew. Chem. Int. Ed. 2013, 52, 14152-14156
  • Cabanetos, W. Bentoumi, E. Blart, Y. Pellegrin, V. Montembault, Y. Bretonnière, C. Andraud, L. Mager, L. Fontaine, F. Odobel, Polym. Adv. Technol. 2013, 24, 473-477.
  • T. T. N’Guyen, G. Contrel, V. Montembault, G. Dujardin, L. Fontaine, Polym. Chem.20156, 3024-3030
  • Feng, F. Calvayrac, V. Montembault, L. Fontaine, J. Phys.: Conf. Series 2015, 633, 012003/1-012003/8.
  • D. A. N'Guyen, V. Montembault, S. Piogé, S. Pascual, L. Fontaine, J. Polym. Sci. Part A: Polym. Chem. 2017, 55, 4051-4061. (DOI: 10.1002/pola.20170550).
  • M. Le Bohec, S. Piogé, S. Pascual, L. Fontaine, J. Polym. Sci. Part A: Polym. Chem. 2017, 55, 3597-3306. (DOI: 10.1002/pola.28742).
  • Gharbi, F. Salles, P. Mathieu, C. Amiens, V. Collière, Y. Coppel, K. Philippot, L. Fontaine, V. Montembault, L. S. Smiri, D. Ciuculescu-Pradines, New J. Chem. 2017, 41, 11898
  • Blin, A Niederberger, L. Benyahia, J. Fresnais, V. Montembault, L. Fontaine, Polym. Chem. 2018, DOI :10.1039/c8py01006d

Hyperthermia-sensitive hybrid nanoparticules and magneto-sensitive hydrogels

Magnetic hybrid nanoparticles have been obtained from iron oxide nanoparticles (IONPs) and (di)furan-functionalized (di)phosphonic acid-terminated poly(ethylene oxide)s. The reversibility of the Diels-Alder reaction between the furan functionality(ies) and maleimide derivatives has been used to design hyperthermia-sensitive hybrid nanoparticles and thermo-sensitive double-crosslinked networks using magnetic iron oxide nanoparticles as crossing points, making these materials potential candidates for new applications mediated by magnetic hyperthermia stimuli, a key requirement for long-term medical therapy.

 

  Researchers

  • Véronique Montembault
  • Sagrario Pascual
  • Lazhar Benyahia
  • Florent Calvayrac
  • Laurent Fontaine

Related papers

  • T. T. N'Guyen, K. Oussadi, V. Montembault, L. Fontaine, J. Polym. Sci., A: Polym. Chem. 2013, 51, 415-423.
  • T. T. N’Guyen, H. T. T. Duong, J. Basuki, V. Montembault, S. Pascual, C. Guibert, J. Fresnais, C. Boyer, M. R. Whittaker, T. P. Davis, L. Fontaine, Angew. Chem. Int. Ed. 2013, 52, 14152-14156.
  • T. T. N’Guyen, G. Contrel, V. Montembault, G. Dujardin, L. Fontaine, Polym. Chem.20156, 3024-3030.
  • Feng, F. Calvayrac, V. Montembault, L. Fontaine, J. Phys.: Conf. Series 2015, 633, 012003/1-012003/8.
  • Gharbi, F. Salles, P. Mathieu, C. Amiens, V. Collière, Y. Coppel, K. Philippot, L. Fontaine, V. Montembault, L. S. Smiri, D. Ciuculescu-Pradines, New J. Chem., 2017, 41, 11898.
  • Blin, A. Niederberger, L. Benyahia, J. Fresnais, V. Montembault, L. Fontaine Polym. Chem. 2018, 9, 4642-4650.

Innovative heterofunctional monomers and linkers

Design of innovative hetero-functional monomers (cyclobutene, vinylazlactone, aminoethyl acrylate) as a toolbox for the elaboration of original macromolecular architectures according to controlled/living polymerization processes (RAFT polymerization, NMP, ROMP, ROP) resulting in polyfunctional polymers for potential biomedical applications.

Azlactone-based heterobifunctional linkers that proceed in orthogonal click-like reactions for chemical ligations in biologically relevant medium without releasing any by-product have been successfully synthesized.

 

Researchers

  • Sagrario Pascual
  • Sandie Piogé
  • Véronique Montembault
  • Laurent Fontaine

Related papers

  • Fontaine, H. T. Ho, S. Pascual, V. Montembault, PCT WO2014060357; US 20150285811A1; Japanese Patent n° 6262746 (2017)
  • T.H. Ho, M.E. Levere, S. Pascual, V. Montembault, N. Casse, A. Caruso, L. Fontaine, Polym. Chem. 2013, 4, 675-685
  • Le, G. Morandi, S. Legoupy, S. Pascual, V. Montembault, L. Fontaine, Eur. Polym. J. 2013, 49, 972-983
  • T. Ho, S. Pascual, V. Montembault, N. Casse, L. Fontaine, Polym. Chem. 2014, 5, 5542
  • Leroux, V. Montembault, S. Pascual, W. Guérin, S. M. Guillaume, L. Fontaine, Polym. Chem. 2014, 5, 3476-3486.
  • Delplace, S. Harrisson, H. T. Ho, JA. Tardy, Y. Guillaneuf, S. Pascual, L. Fontaine, J. Nicolas, Macromolecules 2015, 48(7), 2087-2097
  • T. Ho, J. Coupris, S. Pascual, L. Fontaine, T. Lequeux, T. N. Pham, Polym. Chem. 2015, 6, 4597-4604
  • Leroux, V. Montembault, S. Piogé, S. Pascual, G. Brotons, L. Fontaine, Macromolecules 2016, 49, 4739-4745
  • Leroux, V. Montembault, S. Piogé, S. Pascual, L. Fontaine, Polym. Bull. 2017, 74, 4415-4422
  • Pray-In, C. Boonthip, B. Rutnakornpituk, U. Wichai, V. Montembault, S. Pascual, L. Fontaine, M. Rutnakornpituk, Materials Science & Engineering, C: Materials for Biological Applications 2016, 67, 285-293
  • M. Le Bohec, M. Banère, S. Piogé, S. Pascual, L. Benyahia, L. Fontaine, Polym. Chem. 2016, 7, 6834
  • T. Ho, M. Le Bohec, J. Frémaux, S. Piogé, N. Casse, L. Fontaine, S. Pascual, Macromol. Rapid Commun. 2017, 38, Article Number 1600641
  • T. Ho, A. Bénard, G. Forcher, M. Le Bohec, V. Montembault, S. Pascual, L. Fontaine, Org. Biomol. Chem. 2018, 16, 7124-7128.

Innovative heterofunctional monomers: cyclobutene inimers

Well-defined high molar mass poly(1,4-butadiene)-g-polyesters have been designed either through the grafting from or the grafting through route by the combination of ring-opening metathesis polymerization (ROMP) and organocatalyzed ring-opening polymerization (ROP) of L–lactide (LA) and e-caprolactone (e-CL). Both methodologies provide poly(1,4-butadiene)-g-polyesters having a strictly poly(1,4-butadiene) backbone. Use of the grafting from strategy allowed the synthesis of poly(1,4-butadiene)-g-poly(e-caprolactone) (PBu-g-PCL) with the highest molar mass ever reported. Furthermore, in the solid state upon isothermal crystallization at room temperature, PCL side chains fold while they form an orthorhombic molecular network, building up a self-assembled lamellar phase with large scale d-spacing’s.

 

Researchers

  • Véronique Montembault
  • Sagrario Pascual
  • Sandie Piogé
  • Laurent Fontaine

Related papers

  • Le, G. Morandi, S. Legoupy, S. Pascual, V. Montembault, L. Fontaine, Eur. Polym. J. 2013, 49, 972-983
  • Leroux, V. Montembault, S. Pascual, W. Guérin, S. M. Guillaume, L. Fontaine, Polym. Chem. 2014, 5, 3476-3486.
  • Leroux, S. Pascual, V. Montembault, L. Fontaine, Macromolecules 2015, 89, 3843-3852
  • Leroux, V. Montembault, S. Piogé, S. Pascual, G. Brotons, L. Fontaine, Macromolecules 2016, 49, 4739-4745
  • Leroux, V. Montembault, S. Piogé, S. Pascual, L. Fontaine, Polym. Bull. 2017, 74, 4415-4422

Mikto-arm, comb-like, umbrella-like, and bottlebrush copolymers via ROMP

Tunable macromolecular architectures with unique topological structures and attractive physical/chemical properties from heterofunctional precursors having orthogonal functionalities through combination of RO(M)P and Click chemistry. Copolymers with poly(oxa)norbornene or polybutadiene backbone and amphiphilic biodegradable polyesters or biocompatible poly(ethylene oxide) grafts have been designed from ROMP-able macromonomers, leading to self-organized structures. 

 

Researchers

  • Véronique Montembault
  • Sagrario Pascual
  • Sandie Piogé
  • Laurent Fontaine

Related papers

  • Le, G. Morandi, S. Legoupy, S. Pascual, V. Montembault, L. Fontaine, Eur. Polym. J. 2013, 49, 972-983.
  • Le, V. Montembault, S. Pascual, F. Collette, V. Héroguez, L. Fontaine, Polym. Chem. 2013, 4, 2168-2173.
  • Leroux, V. Montembault, S. Pascual, L. Fontaine, Macromolecules 2015, 48, 3843-3852.
  • A. N'Guyen, F. Leroux, V. Montembault, S. Pascual, L. Fontaine, Polym. Chem. 2016, 7, 1730-1738
  • Leroux, V. Montembault, S. Piogé, S. Pascual, G. Brotons, L. Fontaine, Macromolecules 2016, 49, 4739-4745
  • Leroux, V. Montembault, S. Piogé, S. Pascual, L. Fontaine, Polym. Bull. 2017, 74, 4415-4422
  • A. N'Guyen, V. Montembault, S. Piogé, S. Pascual, L. Fontaine, J. Polym. Sci. Part A: Polym. Chem.201755, 4051-4061
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