Design and synthesis of supramolecular functional monomers bearing urea and norbornene motifs

Lulu Wang; Qifeng Lin; Yagang Zhang; Yanxia Liu; Akram Yasin; Letao Zhang

doi:10.1039/c9ra01852b

Design and synthesis of supramolecular functional monomers bearing urea and norbornene motifs

RSC Adv. 2019 Jun 27;9(35):20058-20064. doi: 10.1039/c9ra01852b. eCollection 2019 Jun 25.

Authors

Lulu Wang^{1

2

3}, Qifeng Lin⁴, Yagang Zhang^{1

2

3}, Yanxia Liu^{1

2

3}, Akram Yasin², Letao Zhang²

Affiliations

¹ Department of Chemical and Environmental Engineering, Xinjiang Institute of Engineering Urumqi 830023 China ygzhang@ms.xjb.ac.cn +86-991-3838957 +86-18129307169.
² Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences Urumqi 830011 China.
³ University of Chinese Academy of Sciences Beijing 100049 China.
⁴ Xinjiang Institute of Ecology and Geography, Chinese Academy of Sciences Urumqi Xinjiang 830011 China.

Abstract

Three sets of functional monomers namely urea-based, 2-ureido-4[1H]-primidone (UPy)-based and norbornene based functional monomers were designed and synthesized. These functional monomers (FM) were obtained in decent yields using amine and isocyanate/norbornene as starting materials. Methacrylate and styrene isocyanate with 1,4-diaminobutane/tris(2-aminoethyl)amine were chosen for the synthesis of symmetrical, asymmetrical and three-branched urea-functional monomers, respectively. UPy-based FMs were synthesized with isocyanate and 2-amino-4-hydroxy-6-methylpyrimidine. The synthesis of these monomers feature short reaction times, mild reaction conditions and no need for column chromatographic purification. Furthermore, the norbornene based FM was used for preparing molecularly imprinted polymers (MIPs) by Ring-Opening Metathesis Polymerization (ROMP). Results showed that these synthetic routes represent a convenient and useful approach for synthesis of novel functional monomers.