Covalent Organic Framework Based on Azacalix[4]arene for the Efficient Capture of Dialysis Waste Products

Abstract

Azacalix[n]arenes (ACAs) are lesser-known cousins of calix[n]arenes that contain amine bridges instead of methylene bridges, so they generally have higher flexibility due to enlarged cavities. Herein, we report a highly substituted cationic azacalix[4]arene-based covalent organic framework (ACA-COF) synthesized by the Zincke reaction under microwave irradiation. The current work is a rare example of a synthetic strategy that utilizes the chemical functionalization of an organic macrocycle to constrain its conformational flexibility and, thereby, produce an ordered material. Considering the ACA cavity dimensions, and the density and diversity of the polar groups in ACA-COF, we used it for adsorption of uric acid and creatinine, two major waste products generated during hemodialysis treatment in patients with renal failure. This type of application, which has the potential to save ∼400 L of water per patient per week, has only been recognized in the last decade, but could effectively address the problem of water scarcity in arid areas of the world. Rapid adsorption rates (up to k = 2191 g mg-1 min-1) were observed in our COF, exceeding reported values by several orders of magnitude.