Preparation of the amorphous embolic agents from glyceryl triallyl ether via a photo-driven radical-mediated [3 + 2] cyclopolymerization

Transcatheter arterial embolization is an established treatment for hepatocellular carcinoma (HCC). However, the existing embolic materials still have some shortcomings, e.g., particle clumping can cause catheter occlusion. In this study, after the synthesis of monomer glyceryl triallyl ether monomer (GE), amorphous embolic agent (PGE) was synthesized by photopolymerization in the presence of GE and photoinitiator. Combined with RT-IR, TG and GPC, we verified that the polymerization followed a photo-driven radical-mediated [3 + 2] cyclopolymerization mechanism (PRMC) through experimental and modeled NMR. The macromolecular properties such as polymerization profile and morphology were studied by TG and SEM–EDS. Finally, the degradation, swelling and migration behavior of PGE were characterized, which indicated that PGE could embolize HCC by blocking the blood supply. In this study, PRMC prevented GE polymerization from degradative chain transfer with 70% yield in an hour, and 200–350 µm PGE was synthesized using this mechanism suitable for clinical use. Graphical abstract