| Abstract Scope |
We report a scalable, green approach to access thiol-norbornene photopolymers by using the ring opening of carbic anhydride. Conventional norbornene functionalization mainly uses 5-norbornene-2-carboxylic acid and its acyl chloride. These compounds are difficult to handle and odorous, and their esterification uses toxic catalysts that require laborious purification. Carbic anhydride is much safer to handle but rarely used outside of hydrogel materials. We have synthesized a series of thiol-norbornene photopolymers by reacting carbic anhydride with amine-terminated polypropylene glycol, amine-terminated polydimethylsiloxane, or alcohol-terminated polycaprolactone. On a commercial resin 3D printer, they can produce true-to-scale 3D aortic arch and branched carotid artery models, as well as microfluidic devices with patent three-dimensional corkscrew channels. Additionally, they show good in vivo and in vitro biocompatibility. Scalable, affordable, and versatile, this new photopolymer platform is poised to widen the usability of vat photopolymerization in biomedical applications and beyond. |