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  • 1. Garcia Gallego, Sandra
    et al.
    Hult, Daniel
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Coating Technology.
    Olsson, Johan V.
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Coating Technology.
    Malkoch, Michael
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Coating Technology.
    Fluoride-Promoted Esterification with Imidazolide-Activated Compounds: A Modular and Sustainable Approach to Dendrimers2015In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 54, no 8, p. 2416-2419Article in journal (Refereed)
    Abstract [en]

    Based on the growing demand for facile and sustainable synthetic methods to structurally perfect polymers, we herein describe a significant improvement of esterification reactions capitalizing on 1,1-carbonyldiimidazole (CDI). Cesium fluoride was shown to be an essential catalyst for these reactions to reach completion. This approach was successfully applied to the synthesis of structurally flawless and highly functional polyester dendrimers employing traditional and accelerated growth strategies. A sixth generation bis-MPA dendrimer with a molecular weight of 22.080Da and 192 peripheral hydroxy groups was isolated in less than one day of total reaction time. Large quantities of dendrimerswere obtained in high yields (>90%) using simple purification steps under sustainable conditions. The fluoride-promoted esterification (FPE) via imidazolide-activated compounds is wide in scope and constitutes a potentially new approach toward functional polymers and other materials.

  • 2.
    Garcia Gallego, Sandra
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology.
    Nyström, Andreas M.
    Malkoch, Michael
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Coating Technology.
    Chemistry of multifunctional polymers based on bis-MPA and their cutting-edge applications2015In: Progress in polymer science, ISSN 0079-6700, E-ISSN 1873-1619, Vol. 48, p. 85-110Article, review/survey (Refereed)
    Abstract [en]

    Polymers play an important role in the advancement of materials for use in cutting-edge applications. A direct consequence of an increased demand for more sophisticated materials has been a drive toward developing polymers that exhibit a higher level of structural control, especially in terms of the number and type of functionalities provided within the polymer framework. A family of polymers that meets such a challenge is based on the readily available AB2 monomer 2,2-bismethylolpropionic acid (bis-MPA) building block. Due to the ease with which the monomers can be synthesized, an array of multifunctional polymers have been produced including monodisperse dendrimers and dendrons and well-defined linear polymers as well as linear-dendritic hybridizations. This review outlines the evolution of the synthetic strategies for developing novel polymeric architectures based on bis-MPA and their assessment in both solution and substrate-based innovative applications.

  • 3.
    García-Gallego, Sandra
    et al.
    University of Cambridge, UK.
    Bernardes, G. J. L.
    Carbon-monoxide-releasing molecules for the delivery of therapeutic co in vivo2014In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 53, no 37, p. 9712-9721Article in journal (Refereed)
    Abstract [en]

    The development of carbon-monoxide-releasing molecules (CORMs) as pharmaceutical agents represents an attractive and safer alternative to administration of gaseous CO. Most CORMs developed to date are transition-metal carbonyl complexes. Although such CORMs have showed promising results in the treatment of a number of animal models of disease, they still lack the necessary attributes for clinical development. Described in this Minireview are the methods used for CORM selection, to date, and how new insights into the reactivity of metal-carbonyl complexes in vivo, together with advances in methods for live-cell CO detection, are driving the design and synthesis of new CORMs, CORMs that will enable controlled CO release in vivo in a spatial and temporal manner without affecting oxygen transport by hemoglobin.

  • 4. García-Gallego, Sandra
    et al.
    Díaz, L.
    Jiménez, J. L.
    Gómez, R.
    De La Mata, F. J.
    Muñoz-Fernández, M. A.
    HIV-1 antiviral behavior of anionic PPI metallo-dendrimers with EDA core2015In: European Journal of Medicinal Chemistry, ISSN 0223-5234, E-ISSN 1768-3254, Vol. 98, p. 139-148Article in journal (Refereed)
    Abstract [en]

    The development of novel strategies to prevent HIV-1 infection is of outstanding relevance. Metal complexes of Cu2+, Ni2+, Co2+ and Zn2+ derived from sulfonated and carboxylated poly(propylene imine) dendrimers with ethylenediamine core were evaluated as tunable antiviral agents against HIV-1. After demonstrating their biocompatibility, specific trends in the antiviral properties were found, related to both the dendritic scaffold (peripheral group, generation) and the bound metal ions (sort, amount). In HEC-1A and VK-2 cell lines, as model of the first barrier against HIV-1 infection, a high preventive inhibitory action was found, which also avoided virus internalization inside cells and inhibited both CCR5 and CXCR4 HIV-1 strains. In peripheral blood mononuclear cells (PBMC), as model of the second barrier, a dual preventive and therapeutic behavior was observed. A rational design of such metallodendrimers opens new avenues for the production of versatile and efficient treatments against HIV-1 infection.

  • 5.
    Granskog, Viktor
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology.
    Garcia-Gallego, Sandra
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology.
    Zhang, Yuning
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology.
    Malkoch, Michael
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology.
    Adhesion-enhancing primer for high-performance bone adhesive2017In: Abstracts of Papers of the American Chemical Society, ISSN 0065-7727, Vol. 253Article in journal (Other academic)
  • 6.
    Hult, Daniel
    et al.
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology, Coating Technology.
    Garcia-Gallego, Sandra
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology, Coating Technology.
    Ingverud, Tobias
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology, Coating Technology.
    Andrén, Oliver
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology.
    Malkoch, Michael
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology, Coating Technology.
    Degradable High Tg Sugar Derived Polycarbonates from Isosorbide and Dihydroxyacetone2018In: Polymer Chemistry, ISSN 1759-9954, E-ISSN 1759-9962, Vol. 9, no 17, p. 2238-2246Article in journal (Refereed)
    Abstract [en]

    Polycarbonates from isosorbide and dihydroxyacetone (DHA) have been synthesised using organocatalytic step-growth polymerization of their corresponding diols and bis-carbonylimidazolides monomers. By choice of feed ratio and monomer activation, either isosorbide or ketal protected DHA, random and alternating poly(Iso-co-DHA) carbonates have been formed. Thermal properties by DSC and TGA were herein strongly correlated to monomer composition. Dilution studies using 1H-NMR of a model compound DHA-diethyl carbonate in acetonitrile and deuterated water highlighted the influence of α-substituents on the keto/hydrate equilibrium of DHA. Further kinetics studies of in the pH* range of 4.7 to 9.6 serve to show the hydrolytic pH-profile of DHA-carbonates. The Hydrolytic degradation of deprotected polymer pellets show an increased degradation with increasing DHA content. Pellets with a random or alternating configuration show different characteristics in terms of mass loss and molecular weight loss profile over time.

  • 7.
    Olsson, J. V.
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Coating Technology.
    Hult, Daniel
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Coating Technology.
    Garcia-Gallego, Sandra
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Coating Technology.
    Malkoch, Michael
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Coating Technology.
    Fluoride-promoted carbonylation polymerization: A facile step-growth technique to polycarbonates2017In: Chemical Science, ISSN 2041-6520, E-ISSN 2041-6539, Vol. 8, no 7, p. 4853-4857Article in journal (Refereed)
    Abstract [en]

    Fluoride-Promoted Carbonylation (FPC) polymerization is herein presented as a novel catalytic polymerization methodology that complements ROP and unlocks a greater synthetic window to advanced polycarbonates. The overall two-step strategy is facile, robust and capitalizes on the synthesis and step-growth polymerization of bis-carbonylimidazolide and diol monomers of 1,3- or higher configurations. Cesium fluoride (CsF) is identified as an efficient catalyst and the bis-carbonylimidazolide monomers are synthesized as bench-stable white solids, easily obtained on 50-100 g scales from their parent diols using cheap commercial 1,1′-carbonyldiimidazole (CDI) as activating reagent. The FPC polymerization works well in both solution and bulk, does not require any stoichiometric additives or complex settings and produces only imidazole as a relatively low-toxicity by-product. As a proof-of-concept using only four diol building-blocks, FPC methodology enabled the synthesis of a unique library of polycarbonates covering (i) rigid, flexible and reactive PC backbones, (ii) molecular weights 5-20 kg mol-1, (iii) dispersities of 1.3-2.9 and (iv) a wide span of glass transition temperatures, from -45 up to 169 °C.

  • 8.
    Olsson, Johan V.
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Coating Technology.
    Hult, Daniel
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology.
    Cai, Yanling
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology.
    Garcia-Gallego, Sandra
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology.
    Malkoch, Michael
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Coating Technology.
    Reactive imidazole intermediates: simplified synthetic approach to functional aliphatic cyclic carbonates2014In: Polymer Chemistry, ISSN 1759-9954, E-ISSN 1759-9962, Vol. 5, no 23, p. 6651-6655Article in journal (Refereed)
    Abstract [en]

    Reactive imidazole intermediates based on AB(2) and A(3) monomers, i.e. bis(methylol) propionic acid (bis-MPA) and trimethylolpropane (TMP) have successfully been synthesized and isolated on a 100 gram scale via a facile synthetic protocol using 1,1' -carbonyldiimidazole (CDI) as a key reagent. The robustness of the imidazole intermediates as bench stable precursors enabled the synthesis of a library of functional cyclic carbonates bearing relevant functionalities including hydrophilic PEGs, bioactive cholesterol and clickable groups. A number of functional polycarbonates were obtained by ring-opening polymerization, and their relevance in biomedical applications was highlighted by their low cytotoxicity on human dermal fibroblasts (hDF).

1 - 8 of 8
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