Diacetylene-Functionalized Dendrons: Self-Assembled and Photopolymerized Three-Dimensional Networks for Advanced Self-Healing and Wringing Soft Materials

Abstract

The physical properties of supramolecular soft materials strongly depend on the molecular packing structures constructed by thermodynamically and kinetically controlled molecular self-assembly. To investigate the relationship between molecular function and self-assembled molecular packing structure, a series of diacetylene (DA)-based supramolecules was synthesized by chemically connecting flexible dendrons to DA with amide (aDA–D) or ester (eDA–D) functions. The three-dimensional (3D) organogel network of amide-functionalized aDA–D was prepared in both polar and nonpolar solvents due to the intermolecular hydrogen bonding. 3D networks of aDA–D can be further stabilized by topochemical photopolymerization. The self-healing behavior of aDA–D was observed in the sheet-like structure formed in n-dodecane by the hydrophobic interaction between the gelator and solvent. The wringing behavior of aDA–D was also demonstrated using the dynamic interaction of amide function with n-butanol solvent. Kinetically controlled and photostabilized 3D networks can be a key component from biomedical devices to soft robotic applications.