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Thiol-triggered deconstruction of bifunctional silyl ether terpolymers via an SNAr-triggered cascade.
Brown, Christopher M; Husted, Keith E L; Wang, Yuyan; Kilgallon, Landon J; Shieh, Peyton; Zafar, Hadiqa; Lundberg, David J; Johnson, Jeremiah A.
Afiliación
  • Brown CM; Department of Chemistry, Massachusetts Institute of Technology 77 Massachusetts Avenue Cambridge MA 02139 USA jaj2109@mit.edu.
  • Husted KEL; Department of Chemistry, Massachusetts Institute of Technology 77 Massachusetts Avenue Cambridge MA 02139 USA jaj2109@mit.edu.
  • Wang Y; Department of Chemistry, Massachusetts Institute of Technology 77 Massachusetts Avenue Cambridge MA 02139 USA jaj2109@mit.edu.
  • Kilgallon LJ; Department of Chemistry, Massachusetts Institute of Technology 77 Massachusetts Avenue Cambridge MA 02139 USA jaj2109@mit.edu.
  • Shieh P; Department of Chemistry, Massachusetts Institute of Technology 77 Massachusetts Avenue Cambridge MA 02139 USA jaj2109@mit.edu.
  • Zafar H; Department of Chemistry, Massachusetts Institute of Technology 77 Massachusetts Avenue Cambridge MA 02139 USA jaj2109@mit.edu.
  • Lundberg DJ; Department of Chemistry, Massachusetts Institute of Technology 77 Massachusetts Avenue Cambridge MA 02139 USA jaj2109@mit.edu.
  • Johnson JA; Department of Chemical Engineering, Massachusetts Institute of Technology 77 Massachusetts Avenue Cambridge MA 02139 USA.
Chem Sci ; 14(33): 8869-8877, 2023 Aug 23.
Article en En | MEDLINE | ID: mdl-37621440
While Si-containing polymers can often be deconstructed using chemical triggers such as fluoride, acids, and bases, they are resistant to cleavage by mild reagents such as biological nucleophiles, thus limiting their end-of-life options and potential environmental degradability. Here, using ring-opening metathesis polymerization, we synthesize terpolymers of (1) a "functional" monomer (e.g., a polyethylene glycol macromonomer or dicyclopentadiene); (2) a monomer containing an electrophilic pentafluorophenyl (PFP) substituent; and (3) a cleavable monomer based on a bifunctional silyl ether . Exposing these polymers to thiols under basic conditions triggers a cascade of nucleophilic aromatic substitution (SNAr) at the PFP groups, which liberates fluoride ions, followed by cleavage of the backbone Si-O bonds, inducing polymer backbone deconstruction. This method is shown to be effective for deconstruction of polyethylene glycol (PEG) based graft terpolymers in organic or aqueous conditions as well as polydicyclopentadiene (pDCPD) thermosets, significantly expanding upon the versatility of bifunctional silyl ether based functional polymers.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Chem Sci Año: 2023 Tipo del documento: Article Pais de publicación: Reino Unido
Texto completo
Añadir a Mi BVS
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XML
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Chem Sci Año: 2023 Tipo del documento: Article Pais de publicación: Reino Unido