Synthesis and characterization of fluorinated biocompatible polyesters

Fluorinated biocompatible polyesters represent a class of functional polymers that combine the desirable biodegradability of traditional aliphatic polyesters (polylactid acid, polylactic-co-glycolic acid) with the unique physicochemical properties conferred by fluorine atoms.[1] Naturally occurring fluorinated polymers are extremely rare, therefore post-polymerization modification strategies are required for decoration of polyesters with fluorinated ligands. In the framework of our studies dealing with the design and development of multifunctional polymeric nanosystems for drug delivery, [2-4] this presentation focuses on functionalization strategies for introducing magnetically-equivalent fluorine moieties into polyester backbones and related copolymers with polyethyleneglycol (PEG). Fluorinated ligands have been synthetized by a multi-step pathway starting from tris(hydroxymethyl)aminomethane (trizma), selected as inner core, to obtain a three-armed fluorinated PEG chain with twenty-seven equivalent fluorine atoms. Structural characterization of the compounds was performed using mono- and bidimensional NMR experiments and mass spectrometry. The grafting of branched fluorinated ligands with different polymeric scaffolds will allow to combine a degree of fluorination suitable for imaging applications (19F NMR) with amphiphilic properties for nanomedicine purposes.