Abstract
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 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 “click” reaction using Ru(bpy)3Cl2 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.
Highlights
Polytetrahydrofuran (PTHF) is an extremely versatile polyether used as adhesives and biomedical and elastomeric materials [1,2,3,4,5]
KOH is an appropriate catalyst for the synthesis of unsaturated polytetrahydrofuran (UPTHF)
Various brunching units could lead to applications in different abundance of active hydroxyl-side groups can be used as a hydrogel material, whereas PTHFs with a Carboxyl Branching Unit (PTHFbut) being fields
Summary
Polytetrahydrofuran (PTHF) is an extremely versatile polyether used as adhesives and biomedical and elastomeric materials [1,2,3,4,5]. Among the various ways about the post-modification of unsaturated polymers, the most widely used is the thiol-ene “click” reaction. Based on the above considerations and inspired by previous research outcomes, we reported a simple strategy to synthesize UPTHF via condensation polymerization and post-polymerization modification of UPTHF to obtain side-chain functionalized PTHFs via the blue-light photocatalytic thiol-ene reaction. Blue light was used to induce the thiol-ene reaction between UPTHF and a range of thiol-containing compounds, such as mercaptoethanol, n-butyl mercaptan, mercaptopropionic acid, as well as methoxy- polyethylene glycol-thiol (mPEG-SH) (Mn = 750 g mol−1 ), to obtain different PTHFs named PTHFOH , PTHFbut , PTHFacid , and PTHFmPEG , respectively Figure 1).
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