Abstract
Helical assemblies of organic dyes are ubiquitous chiral organic materials, with valuable properties including chiroptical switching due to the dynamic nature of supramolecular chirality. Herein, we report a novel chiral bis-perylene diimide macrocycle, which acts as a discrete molecular model for a chiral supramolecular assembly. Point chirality is installed through amino acid-derived imide groups which, upon macrocyclization, is translated into helical chirality in the perylene diimide dimer. In solution, the macrocycle's chiroptical properties are switchable, with both the sign (+/-) and amplitude (on/off) of the signal tuned using solvent and molecular recognition stimuli respectively. The chiral structure-property relationships identified from this macrocycle are important for the design of high fidelity supramolecular chiroptical switches.