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1.
  • Auer, F, et al. (författare)
  • Switchable assembly of stable, ordered molecular layers
  • 1999
  • Ingår i: Chemistry - A European Journal. - 0947-6539 .- 1521-3765. ; 5, s. 1150-1159
  • Tidskriftsartikel (refereegranskat)abstract
    • Bisamidines can be assembled on self-assembled monolayers of mercaptoalkanoic acids on gold to form stable and ordered but pH-switchable layers (see diagram). At basic pH the layers are stable and charge selective towards charged surfactants and plasma proteins. The system can potentially be used to reversibly introduce new surface properties for given applications that use one single substrate.
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2.
  • Stamm, Arne, et al. (författare)
  • Pinene-Based Oxidative Synthetic Toolbox for Scalable Polyester Synthesis
  • 2021
  • Ingår i: JACS Au. - : American Chemical Society (ACS). - 2691-3704. ; 1:11, s. 1949-1960
  • Tidskriftsartikel (refereegranskat)abstract
    • Generation of renewable polymers is a long-standing goal toward reaching a more sustainable society, but building blocks in biomass can be incompatible with desired polymerization type, hampering the full implementation potential of biomaterials. Herein, we show how conceptually simple oxidative transformations can be used to unlock the inherent reactivity of terpene synthons in generating polyesters by two different mechanisms starting from the same alpha-pinene substrate. In the first pathway, alpha-pinene was oxidized into the bicyclic verbanone-based lactone and subsequently polymerized into star-shaped polymers via ring-opening polymerization, resulting in a biobased semicrystalline polyester with tunable glass transition and melting temperatures. In a second pathway, polyesters were synthesized via polycondensation, utilizing the diol 1-(1'-chydroxyethyl)-3-(2'-hydroxyethyl)-2,2-dimethylcyclobutane (HHDC) synthesized by oxidative cleavage of the double bond of alpha-pinene, together with unsaturated biobased diesters such as dimethyl maleate (DMM) and dimethyl itaconate (DMI). The resulting families of terpenebased polyesters were thereafter successfully cross-Iinked by either transetherification, utilizing the terminal hydroxyl groups of the synthesized verbanone-based materials, or by UV irradiation, utilizing the unsaturation provided by the DMM or DMI moieties within the HHDC-based copolymers. This work highlights the potential to apply an oxidative toolbox to valorize inert terpene metabolites enabling generation of biosourced polyesters and coatings thereof by complementary mechanisms.
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