Design of an Amphiphilic Perylene Diimide for Optical Recognition of Anticancer Drug through a Chirality-Induced Helical Structure

Introduction of chirality into a supramolecular self-assembly system plays an indispensable role in attaining specific molecular recognition ability. Herein, a chiral anticancer drug 5 '-deoxy-5-fluorouridine (5 ' DFU) was explored for inducing the self-assembly of a cationic perylene diimide derivative containing boronic acid groups (PDI-PBA) into a highly ordered right-handed helical structure. As a result, PDI-PBA exhibited a molecular recognition ability towards 5 ' DFU among other cis-diols and anticancer drugs. With the help of a dynamic covalent bond and favorable hydrogen-bonding interactions, chirality transfer from chiral 5 ' DFU to achiral PDI-PBA breaks down the strong pi-pi stacking of PDI-PBA and makes it reorganize into highly ordered helical supramolecular structures. This work provides an insight into chiral anticancer drug tuning interactions of pi-chromophores and the inducement of hierarchical self-assembly to achieve specific molecular recognition.