Poly(sebacoyl diglyceride) Cross-Linked by Dynamic Hydrogen Bonds: A Self-Healing and Functionalizable Thermoplastic Bioelastomer.

Biodegradable and biocompatible elastomers (bioelastomers) could resemble the mechanical properties of extracellular matrix and soft tissues and, thus, are very useful for many biomedical applications. Despite significant advances, tunable bioelastomers with easy processing, facile biofunctionalization, and the ability to withstand a mechanically dynamic environment have remained elusive. Here, we reported new dynamic hydrogen-bond cross-linked PSeD-U bioelastomers possessing the aforementioned features by grafting 2-ureido-4[1H]-pyrimidinones (UPy) units with strong self-complementary quadruple hydrogen bonds to poly(sebacoyl diglyceride) (PSeD), a refined version of a widely used bioelastomer poly(glycerol sebacate) (PGS). PSeD-U polymers exhibited stronger mechanical strength than their counterparts of chemically cross-linked PSeD and tunable elasticity by simply varying the content of UPy units. In addition to the good biocompatibility and biodegradability as seen in PSeD, PSeD-U showed fast self-healing (within 30 min) at mild conditions (60 °C) and could be readily processed at moderate temperature (90-100 °C) or with use of solvent casting at room temperature. Furthermore, the free hydroxyl groups of PSeD-U enabled facile functionalization, which was demonstrated by the modification of PSeD-U film with FITC as a model functional molecule.