Photochemical Functionalization of Polymer Surfaces for Microfabricated Devices

Abstract

Herein we report the topochemical modification of polymer surfaces with perfluorinated aromatic azides. The aryl azides, which have quaternary amine or aldehyde functional groups, were linked to the surface of the polymer by UV irradiation. The polymer substrates used in this study were cyclic olefin copolymer and poly(methyl methacrylate). These substrates were characterized before and after modification using reflection-absorption infrared spectroscopy, sessile water contact angle measurements, and X-ray photoelectron spectroscopy. Analysis of the surface confirmed the presence of aromatic groups with aldehyde or quaternary amine functionality. Enzyme immobilization and patterning onto polymer surfaces were studied using confocal microscopy. Enzymatic digests of protein were carried out on modified probes manufactured from thermoplastic substrates, and the resulting peptide analysis was completed using matrix-assisted laser desorption/ionization mass spectrometry. The use of functionalized perfluorinated aromatic azides allows the surface chemistry of thermoplastics to be tailored for specific lab-on-a-chip applications.

Towards a biocompatible artificial lung: Covalent functionalization of poly(4-methylpent-1-ene) (TPX) with cRGD pentapeptide

“…Conceptually, we planned to first functionalize the hydrocarbon TPX 2 via UV-mediated nitrene insertion to form polymer derivative 4 (Scheme 1) [12–14]. Therefore, nitrene precursor 3 was modified with an oligo(ethylene glycol) linker, which served as a spacer unit between the polymer and the bioactive c RGD domain [15].…”

The ability of triplet nitrenes to abstract hydrogen atoms

“…Singlet nitrene intermediates are useful in applications such as photoaffinity labeling, crosslinking polymers, and modification of surfaces 1–9. The use of singlet nitrenes in these applications is due to their ability to insert efficiently into surrounding chemical bonds 10.…”

Surface functionalization of cyclic olefin copolymer with aryldiazonium salts: A covalent grafting method

“…UV illumination has been tested successfully to activate COC surfaces in order to graft DNA or acrylic monomers onto them [19,20]. Another approach tested the reaction of a COC surface with UV-sensitive molecules such as an anthraquinone photolinker [21], benzophenone [22], benzoin methyl ether [23], and aryl azide [24]. Apart from these approaches, UV illumination was tested to photograft polymers onto a COC surface.…”

“…Apart from these approaches, UV illumination was tested to photograft polymers onto a COC surface. That way, microfluidic channels hollowed in COC were patterned by N-vinylpyrrolidone, acrylic and methacrylate films [24][25][26][27][28]. As a large amount of methacrylate monomers is available, COC surfaces progressively gained new functionalities including low protein adsorption, adjustable electroosmotic flow or immobilization of reactive groups ready to use with biomolecules.…”