Functionalization of pristine graphene for the synthesis of covalent graphene–polyaniline nanocomposite

Polyaniline was covalently grafted on pristine few-layer graphene via a perfluorophenyl azide-mediated coupling chemistry.

Synthesis of Carbohydrate-Grafted Glycopolymers Using a Catalyst-Free, Perfluoroarylazide-Mediated Fast Staudinger Reaction

Glycopolymers have gained increasing importance in investigating glycan-lectin interactions, as drug delivery vehicles and in modulating interactions with proteins. The synthesis of these glycopolymers is still a challenging and rigorous exercise. In this regard, the highly efficient click reaction, copper (I)-catalyzed alkyne-azide cycloaddition, has been widely applied not only for its efficiency but also for its tolerance of the appended carbohydrate groups. However, a significant drawback of this method is the use of the heavy metal catalyst which is difficult to remove completely, and ultimately toxic to biological systems. In this work, we present the synthesis of carbohydrate-grafted glycopolymers utilizing a mild and catalyst-free perfluorophenyl azide (PFPA)-mediated Staudinger reaction. Using this strategy, mannose (Man) and maltoheptaose (MH) were grafted onto the biodegradable poly(lactic acid) (PLA) by stirring a PFAA-functionalized PLA with a phosphine-derivatized Man or MH in DMSO at room temperature within an hour. The glycopolymers were characterized by 1H-NMR, 19F-NMR, 31P-NMR and FTIR.

Novel N-chloramine precursors for antimicrobial application: synthesis and facile covalent immobilization on polyurethane surface based on perfluorophenyl azide (PFPA) chemistry

To control the pathogen cross contaminations on medical material surface, there is a pressing need to develop antimicrobial materials with highly efficacious surface biocidal activity. In this work, N-chloramine precursors containing a quaternary ammonium unit and perfluorophenyl azide unit were synthesized and covalently immobilized on inert polyurethane (PU) film upon UV light irradiation. The surface modification was confirmed by contact angle, Fourier transform infrared (ATR FTIR) spectroscopy, X-ray photoelectron spectroscopy (XPS), and atomic force microscopy (AFM) analyses. After bleaching treatment, satisfactory biocidal activity was achieved for the surface-modified PU films. It was found that the introduced surface QA center contributed an even faster surface contact killing behavior and that precursors with a longer structural linker caused higher surface chlorine content and higher antimicrobial efficacy. This approach provides a novel and facile method that enables the covalent immobilization of N-chloramine precursors on inert polymeric surface to produce durable antimicrobial materials.

2D and 3D surface photopatterning via laser-promoted homopolymerization of a perfluorophenyl azide-substituted BODIPY

A direct laser-writing methodology, harnessing the homopolymerization of a perfluorophenyl-azide BODIPY molecule, which forms red fluorescent nanostructures of controlled height is described.