Visible light-induced thione-ene cycloaddition reaction for the surface modification of polymeric materials

• Published in: Chinese chemical letters Vol. 29; no. 1; pp. 157 - 160
• Main Authors: Wang, Li, Wang, Yi, Chen, Dong, Yang, Wantai
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 2018
• Subjects: LDPE; Polymeric materials; Surface modification; Thone-ene cycloaddition; Visible light; Surface modification; Visible light; Thone-ene cycloaddition; Polymeric materials; LDPE
• ISSN: 1001-8417; 1878-5964
• DOI: 10.1016/j.cclet.2017.08.001

High-tech applications often demand the surface modification of polymeric materials using chemo- selective reactions that can proceed under mild conditions. In this paper, a feasible method for the surface modification of polymeric materials with low density polyethylene （LDPE） films as model substrates based on visible light-induced thione-ene cycloaddition reaction is proposed. This strategy includes three steps： 3-（（6-Hydroxyhexyl）oxy）-9H-xanthene-9-thione （HXT） containing visible light-reactive thio- carbonyl groups was firstly synthesized; Then thiocarbonyl groups were introduced onto LDPE films previously surface-grafted with poly（styrene-co-maleic anhydride） brushes by the reaction between the hydroxyl groups of HXT and anhydride groups; Functional alkenes were finally fixed onto the surface of LDPE films by thione-ene cycloaddition reaction conducted under visible light at room temperature （r.t.）, By FTIR, UV-vis spectroscopy, water contact angle test and XPS, we found that four typical functional alkenes, poly（ethylene glycol） methyl ethermethacrylate, 2-（perflurooctyl）ethyl methacrylate, 2, 3- dibromopropyl acrylate, and diethyl vinylphosphonate, can be successfully ligated, which confirmed the effectiveness and versatility of the present method.