American Chemical Society
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Photocurable Urushiol Analogues Bearing Methacryloxy-Containing Side chains

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journal contribution
posted on 2019-03-08, 00:00 authored by Hirohmi Watanabe, Mariko Takahashi, Hideyuki Kihara, Masaru Yoshida
Photocurable urushiol analogues were synthesized using eugenol (an ingredient of clove oil) as the starting material. Photo-induced radical polymerization with 2,2-dimethoxy-2-phenylacetophenone as a photo-initiator took place in the film prepared from the urushiol analogue-bearing methacryloxy groups at the ends of their side chains. Successful polymerization was confirmed by infrared spectroscopy measurements of the film before and after photo-irradiation. Strain-induced elastic buckling instability for mechanical measurement tests revealed that the Young’s moduli of the photo-irradiated samples were 4–5 times higher than the films without photo-irradiation. This was attributed to the formation of a highly cross-linked structure through polymerization of the methacrylic moieties and oxidative polymerization of the catechol moieties. Photo-induced surface texturing was also performed for the films prepared on a substrate using a photomask. Negative-tone patterns were successfully obtained after development by soaking in cyclohexanone over several minutes. The preparation of such patterned surfaces was of particular relevance as the obtained surface can serve as a scaffold for cell adhesion, protein immobilization, and the immobilization of other chemicals with spatial disposition.