Articles producció científica> Química Analítica i Química Orgànica

SET-LRP of the Hydrophobic Biobased Menthyl Acrylate

  • Datos identificativos

    Identificador: imarina:5132119
    Autores:
    Bensabeh N., Ronda J., Galià M., Cádiz V., Lligadas G., Percec V.
    Resumen:
    Cu(0) wire-catalyzed single electron transfer¿living radical polymerization (SET-LRP) of (−)-menthyl acrylate, a biobased hydrophobic monomer, was investigated at 25 °C in ethanol, isopropanol, ethyl lactate, 2,2,2-trifluoroethanol (TFE), and 2,2,3,3-tetrafluoropropanol (TFP). All solvents are known to promote, in the presence of N ligands, the mechanistically required self-regulated disproportionation of Cu(I)Br into Cu(0) and Cu(II)Br2. Both fluorinated alcohols brought out their characteristics of universal SET-LRP solvents and showed the proper polarity balance to mediate an efficient polymerization of this bulky and hydrophobic monomer. Together with the secondary alkyl halide initiator, methyl 2-bromopropionate (MBP), and the tris(2-dimethylaminoethyl)amine (Me6-TREN) ligand, TFE and TPF mediated an efficient SET-LRP of MnA at room temperature that proceeds through a self-generated biphasic system. The results presented here demonstrate that Cu(0) wire-catalyzed SET-LRP can be used to target polyMnA with different block lengths and narrow molecular weight distribution at room temperature. Indeed, the use of a combination of techniques that include GPC, 1H NMR, MALDI-TOF MS performed before and after thioetherification of bromine terminus via ¿thio¿bromo¿ click chemistry, and in situ reinitiation copolymerization experiments supports the near perfect chain end functionality of the synthesized biobased hydrophobic polymers. These results expand the possibilities of SET-LRP into the area of renewable resources where hydrophobic compounds are widespread.
  • Otros:

    Autor según el artículo: Bensabeh N., Ronda J., Galià M., Cádiz V., Lligadas G., Percec V.
    Departamento: Química Analítica i Química Orgànica
    Autor/es de la URV: Cádiz Deleito, Maria Virginia / Galià Clua, Marina Teresa / Lligadas Puig, Gerard / Ronda Bargalló, Juan Carlos
    Palabras clave: Hashtag Etiqueta «#» @uroweb @residentesaeu @infoAeu
    Resumen: Cu(0) wire-catalyzed single electron transfer¿living radical polymerization (SET-LRP) of (−)-menthyl acrylate, a biobased hydrophobic monomer, was investigated at 25 °C in ethanol, isopropanol, ethyl lactate, 2,2,2-trifluoroethanol (TFE), and 2,2,3,3-tetrafluoropropanol (TFP). All solvents are known to promote, in the presence of N ligands, the mechanistically required self-regulated disproportionation of Cu(I)Br into Cu(0) and Cu(II)Br2. Both fluorinated alcohols brought out their characteristics of universal SET-LRP solvents and showed the proper polarity balance to mediate an efficient polymerization of this bulky and hydrophobic monomer. Together with the secondary alkyl halide initiator, methyl 2-bromopropionate (MBP), and the tris(2-dimethylaminoethyl)amine (Me6-TREN) ligand, TFE and TPF mediated an efficient SET-LRP of MnA at room temperature that proceeds through a self-generated biphasic system. The results presented here demonstrate that Cu(0) wire-catalyzed SET-LRP can be used to target polyMnA with different block lengths and narrow molecular weight distribution at room temperature. Indeed, the use of a combination of techniques that include GPC, 1H NMR, MALDI-TOF MS performed before and after thioetherification of bromine terminus via ¿thio¿bromo¿ click chemistry, and in situ reinitiation copolymerization experiments supports the near perfect chain end functionality of the synthesized biobased hydrophobic polymers. These results expand the possibilities of SET-LRP into the area of renewable resources where hydrophobic compounds are widespread.
    Áreas temáticas: Química Polymers and plastics Polymer science Medicina ii Materials chemistry Materiais Interdisciplinar Farmacia Engenharias iv Engenharias ii Ciências biológicas iii Ciências biológicas ii Ciências biológicas i Ciências agrárias i Ciência de alimentos Chemistry, organic Biotecnología Biomaterials Bioengineering Biochemistry & molecular biology Astronomia / física
    ISSN: 15257797
    Direcció de correo del autor: marina.galia@urv.cat juancarlos.ronda@urv.cat gerard.lligadas@urv.cat
    Identificador del autor: 0000-0002-4359-4510 0000-0002-0668-6600 0000-0002-8519-1840
    Página final: 1268
    Fecha de alta del registro: 2024-09-07
    Volumen de revista: 19
    Versión del articulo depositado: info:eu-repo/semantics/submittedVersion
    Enlace a la fuente original: https://pubs.acs.org/doi/abs/10.1021/acs.biomac.8b00090
    URL Documento de licencia: https://repositori.urv.cat/ca/proteccio-de-dades/
    Referencia al articulo segun fuente origial: Biomacromolecules. 19 (4): 1256-1268
    Referencia de l'ítem segons les normes APA: Bensabeh N., Ronda J., Galià M., Cádiz V., Lligadas G., Percec V. (2018). SET-LRP of the Hydrophobic Biobased Menthyl Acrylate. Biomacromolecules, 19(4), 1256-1268. DOI: 10.1021/acs.biomac.8b00090
    DOI del artículo: 10.1021/acs.biomac.8b00090
    Entidad: Universitat Rovira i Virgili
    Año de publicación de la revista: 2018
    Página inicial: 1256
    Tipo de publicación: Journal Publications
  • Palabras clave:

    Biochemistry & Molecular Biology,Bioengineering,Biomaterials,Chemistry, Organic,Materials Chemistry,Polymer Science,Polymers and Plastics
    Química
    Polymers and plastics
    Polymer science
    Medicina ii
    Materials chemistry
    Materiais
    Interdisciplinar
    Farmacia
    Engenharias iv
    Engenharias ii
    Ciências biológicas iii
    Ciências biológicas ii
    Ciências biológicas i
    Ciências agrárias i
    Ciência de alimentos
    Chemistry, organic
    Biotecnología
    Biomaterials
    Bioengineering
    Biochemistry & molecular biology
    Astronomia / física
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