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Surface Engineering of Organic Polymers by Photo‐induced Free Radical Coupling with p ‐Dimethylaminophenyl Group as A Synthesis Block
Author(s) -
Liao Qingyu,
Chen Dong,
Zhang Xianhong,
Ma Yuhong,
Yang Biao,
Zhao Changwen,
Yang Wantai
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202000082
Subject(s) - polymer chemistry , copolymer , polymer , covalent bond , polypropylene , rhodamine b , materials science , functional polymers , x ray photoelectron spectroscopy , functional group , chemistry , photochemistry , chemical engineering , organic chemistry , catalysis , photocatalysis , engineering
This contribution presents a versatile strategy to transfer unactivated surface C–H bonds of polymeric substrates to C–R–F groups (R stands for a spacer and F stands for functional group) by UV light‐assisted surface free radical coupling. With p‐ dimethylaminophenyl radical as a building block, various reactive groups, such as –CHO, –SH, –B(O)OH, –CN and –SO 3 − , are successfully grafted onto typical commercial polymer substrates including biaxially oriented polypropylene, polyethylene phthalate, ethylene tetrafluoroethylene copolymer and dimethyl silicone rubber. Fluorencence microscope images, X‐ray photoelectron spectroscopy, UV‐vis and fluorescence spectra support that the above functional groups are covalently bonded to the polymer substrates. The concentration of the reactive groups immobilized on the different substrates is in the order of 10 −8 to 10 −7 mmol mm −2 determined by UV‐vis spectrometry. In addition, as a proof‐of‐concept, the introduced functional groups are demonstrated by their special reactions, for example, –CHO reacting with –NH 2 to synthesize Schiff base, –SH to detect silver ions, and the complexes of –C=N and Zn 2+ to degrade Rhodamine B. The results indicate that one can fabricate an integrated molecular library on the surface of polymeric substrates at the molecular level by selecting the building blocks.