Water-Dispersible Porous Aromatic Frameworks with Quasi-Amino Acid Structures via N-H Insertion Reactions.

ABSTRACT

As a class of materials with large specific surface area and chemical stability, porous aromatic frameworks (PAFs) have attracted much attention in the fields of gas adsorption, separation, and catalysis. However, synthetic methods for PAFs have been limited to a few coupling reactions, and PAF powders were usually obtained with a diameter of micrometer size. Here, we demonstrate an efficient N-H insertion reaction of diazoesters in the synthesis of PAFs with a diameter <200 nm. The established polymerization can be performed at room temperature, and four PAFs with different skeletons and composition can be obtained in high yields. The prepared PAFs have appreciable thermal and chemical stabilities. Because of the presence of ester groups in the backbone, the prepared PAFs with α-phenylglycine fragments can be easily obtained through the successive hydrolysis of the ester groups. The synthesized PAFs bearing phenylglycine moieties exhibit good water dispersibility and low cytotoxicity. We further show the potential of these PAFs in drug loading and photodynamic therapy.