Citation: Wang Li, Wang Yi, Chen Dong, Yang Wantai. Visible light-induced thione-ene cycloaddition reaction for the surface modification of polymeric materials[J]. Chinese Chemical Letters, ;2018, 29(1): 157-160. doi: 10.1016/j.cclet.2017.08.001 shu

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

The State Key Laboratory of Chemical Resource Engineering, College of Materials Science and Engineering, Beijing University of Chemical Technology, Beijing 100029, China

Corresponding author: Yang Wantai, yangwt@mail.buct.edu.cn
Received Date: 26 April 2017
Revised Date: 14 June 2017
Accepted Date: 1 August 2017
Available Online: 2 January 2017

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High-tech applications often demand the surface modification of polymeric materials using chemoselective 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 thiocarbonyl 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.
- Visible light,
- Thone-ene cycloaddition,
- Surface modification,
- Polymeric materials,
- LDPE
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