The fabrication of advanced functional polymeric surfaces with well-defined chemical functionalities and complex patterns is critical for a number of diverse applications ranging from biosensors to bio/nanotechnology. Post-polymerization modification (PPM) serves as a powerful tool for tailoring the chemical and mechanical properties of polymer brush surfaces. “Click” reactions have been utilized as means of PPM to design surfaces with multistep reactions in a one-pot fashion. Specifically, thiol-click reactions represent a highly efficient surface modification technique, however, the high-reactivity of thiol-containing monomers hinders their use in most polymerization techniques. The use of a thiolactone (a cyclic thioester) as latent thiol functionality serves as an attractive alternative for synthetic polymer science. Thiolactone chemistry has gained significant attention as a new powerful post-polymerization modification (PPM) “click” strategy involving amine-thiol-ene conjugation. However, thiolactone chemistry has yet to be explored as a modular approach for surface engineering. We demonstrate a versatile PPM approach to synthesize multifunctional polymer brush surfaces based on poly(acrylamide-homocysteine thiolactone) (pAHT). Modification of the brush surfaces with a library of amines generates a reactive thiol precursor, which is available to undergo a sequential base-catalyzed thiol-Michael reaction with functional acrylates and maleimides. Additionally, we employ a one-pot double modification reaction to demonstrate the versatility of thiolactone chemistry as a powerful PPM platform for polymer brush surfaces. Finally, we exploit reactive microcontact printing with fluorescent post-modifiers to design multifunctional, micropatterned, fluorescent surfaces.

Synthesis of thiolactone polymer brushes: Sequential and one-pot reactions to design multifunctional and patterned brush surfaces

2019 Spring National Meeting

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