Single‐point halogenation regulates supramolecular chirality in phenylalanine‐based co‐assembled systems

The construction of chiral materials with precise chirality is of vital importance in biology and chemistry. Despite numerous chiral materials having been fabricated, it still remains a fundamental challenge to understand the chiral propensity with subtle changes of building blocks. Here, the chirality properties of an assembly from chiral phenylalanine gelators and achiral naphthalimide (NI) derivatives were successfully regulated, showing that a minimal difference on the fourth site of the halogenated NI induced great changes of the chirality characteristics of the assembly. The results suggested that hydrogen bonds and π–π stacking interactions are the driving forces of the assemblies, whereas different halogenations indeed lead to the subtle variety of hydrogen bonding interactions and stacking mode between the two molecules. This study provides feasible strategies for precisely modulating supramolecular chirality through single‐point halogenation. © 2021 Society of Industrial Chemistry. A single‐point replacement of halogen atoms on naphthalimide (NI) derivatives efficiently regulated the supramolecular chirality when co‐assembling with typical chiral molecules of C2‐symmetric phenylalanine derivatives. The handedness, helical pitch and diameter of these co‐assemblies were successfully tuned with the variation of halogenated NI derivatives.