Synthesis and Properties of Side-Chain Functionalized Polytetrahydrofuran Derivatives via the Blue-Light Photocatalytic Thiol-Ene Reaction

A series of side-chain functionalized polytetrahydrofuran (PTHF) derivatives were synthesized via the blue-light photocatalytic thiol-ene “click„ reaction. Firstly, unsaturated polytetrahydrofuran (UPTHF) as a new unsaturated polyether was synthesized via condensation polymerizat...

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Bibliographic Details
Main Authors: Xiuzhong Zhu, Ting Bai, Zichao Wang, Jie Liu, Xin Min, Tong Wang, Wanbin Zhang, Xiaodong Fan
Format: Article
Language:English
Published: MDPI AG 2019-04-01
Series:Polymers
Subjects:
Online Access:https://www.mdpi.com/2073-4360/11/4/583
Description
Summary:A series of side-chain functionalized polytetrahydrofuran (PTHF) derivatives were synthesized via the blue-light photocatalytic thiol-ene &#8220;click&#8222; reaction. Firstly, unsaturated polytetrahydrofuran (UPTHF) as a new unsaturated polyether was synthesized via condensation polymerization of cis-2-butene-1,4-diol and trans-1,4-dibromo-2-butene using potassium hydroxide (KOH) as a catalyst. Then, double bonds in the backbone of UPTHF were modified into different pendant functionality side groups by blue-light photocatalytic thiol-ene &#8220;click&#8222; reaction using Ru(bpy)<sub>3</sub>Cl<sub>2</sub> as a photoredox catalyst, obtaining different side-chain functionalized PTHF derivatives. The structure and the morphology of the side-chain functionalized PTHF derivatives was characterized via Fourier-transform infrared spectra (FTIR), nuclear magnetic resonance (NMR), size exclusion chromatography/multi-angle laser light scattering (SEC/MALLS), and differential scanning calorimeter (DSC). The results showed that the blue-light photocatalytic thiol-ene reaction exhibited high efficiency, and all the unsaturated bonds were modified. Different branch units bestowed different performance of PTHF derivatives; we systematically investigated the thermal properties, pH-triggered and temperature-triggered, self-assembly behaviors of different PTHF derivatives.
ISSN:2073-4360