Abstract
Dendrons consisting of two phosphonate functions and three oligo(ethylene glycol) (OEG) chains grafted on a central phenoxyethylcarbamoylphenoxy group were synthesized and investigated as Langmuir monolayers at the surface of water. The OEG chain in the para position was grafted with a t-Bu end-group, a hydrocarbon chain, or a partially fluorinated chain. These dendrons are models of structurally related OEG dendrons that were found to significantly improve the stability of aqueous dispersions of iron oxide nanoparticles when grafted on their surface. Compression isotherms showed that all OEG dendrons formed liquid-expanded Langmuir monolayers at large molecular areas. Further compression led to a transition ascribed to the solubilization of the OEG chains in the aqueous phase. Brewster angle microscopy (BAM) provided evidence that the dendrons fitted with hydrocarbon chains formed liquid-expanded monolayers throughout compression, whilst those fitted with fluorinated end-groups formed crystalline-like domains, even at large molecular areas. Dimyristoylphosphatidylcholine and dendron molecules were partially miscible in monolayers. The deviations to ideality were larger for the dendrons fitted with a fluorocarbon end-group chain than for those fitted with a hydrocarbon chain. Brewster angle microscopy and atomic force microscopy supported the view that the dendrons were ejected from the phospholipid monolayer during the OEG conformational transition and formed crystalline domains on the surface of the monolayer.
Highlights
Dendrimers are monodisperse macromolecules with a regular, highly branched, and well defined three-dimensional architecture, which have garnered interest in nanotechnology, materials science, and medicine [1,2,3]
Oligo(ethylene glycol) (OEG) dendrons have been used as efficient coating agents of iron oxide nanoparticles (IONPs) to improve the dispersibility and stability of these nanoparticles in aqueous
Dendrons consisted of a central phenoxyethylcarbamoyl group coupled to a phenyl group onto which three OEG chains were grafted (Frechet-type dendron), and bearing two phosphonate esters on the phenoxy group. These OEG dendrons are structurally close to the dendrons that have been found to improve the dispersibility and stability of iron oxide nanoparticles (IONPs) in aqueous solutions, a critical property for many studies and applications [8,22]
Summary
Dendrimers are monodisperse macromolecules with a regular, highly branched, and well defined three-dimensional architecture, which have garnered interest in nanotechnology, materials science, and medicine [1,2,3]. Our OEG dendrons consisted of a central phenoxyethylcarbamoyl group coupled to a phenyl group onto which three OEG chains were grafted (Frechet-type dendron), and bearing two phosphonate esters on the phenoxy group These OEG dendrons are structurally close to the dendrons that have been found to improve the dispersibility and stability of iron oxide nanoparticles (IONPs) in aqueous solutions, a critical property for many studies and applications [8,22]. The mixed DMPC/OEG dendron monolayers are model interfaces that can provide insights into the interactions between the components, namely phospholipid and dendron, that form the microbubble shell To this end, 10 dendrons were synthesized and investigated that featured two phosphonic esters and three OEG chains, including a longer one, connected by a phenoxyethylcarbamoylphenoxy group.
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