A variety of polymer-based materials containing reactive chemical groups have been proposed due to their potential applications for catalysis, biological process, and sensing system. The selectivity of the chemical reaction is a crucial aspect in functionalization chemistry. Particularly, in surface chemistry, creating various desired chemical groups on a single surface enables us multi-surface functionalizations, which further allow to mimic highly complex structures in nature. Among the literature, the modification of thin films using functionalizable polymer using useful reactive groups such as carboxylic acid, amine, alcohol, azide, and alkyne is one of versatile and feasible methods. In this work, the post-spincoating modification method was demonstrated to obtain different chemical functionalities on a surface. A critical step in our strategy to form functionalities on surfaces is introducing chemical functional groups on a substrate by depositing stable polymer thin film by crosslinking chemistry. To do so, we have synthesized (2-thioxo-1,3-oxathiolan-5-yl)methyl methacrylate (DTCMMA) and successfully copolymerized it with four different methacrylate monomers, i.e. methyl methacrylate (MMA), ethyl methacrylate (EMA), tert-butyl methacrylate (tBMA), and n-butyl methacrylate (nBMA). 1,3-oxathiolane-2-thione group is known to effectively react with primary amine by nucleophilic ring opening reaction. In this respect, we designed and synthesized a crosslinker releasing amine groups upon the exposure to UV light. A double component system of the copolymer and the light sensitive crosslinker was successfully crosslinked in thin film upon UV illumination under mild conditions. In addition, since 1,3-oxathiolane-2-thione in the crosslinked polymer chains releases thiol upon the ring opening reaction, which could be further utilized to functionalize other functionalities via other efficient chemistries such thiol-ene click reaction. The crosslinked functionalizable copolymeric film allows to immobilize various compounds, leading us to multi-functional surfaces with highly controlled complexity.

1,3-Oxathiolane-2-thione-based photosensitive polymeric system to create multi-chemical surface functionalities

2019 Fall National Meeting

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.