Positional Isomerism Controlled Supramolecular Nanoarchitecture and Circularly Polarized Luminescence in Naphthalene Amphiphiles

Precise control of supramolecular nanoarchitecture and its functionality remains a consistent challenge in chiral materials design. Here, we show that positional isomerism in naphthalene-based amphiphiles governs self-assembly pathways, yielding distinct morphologies with opposite supramolecular chirality. It is found that the L-2-substituted isomer forms left-handed helical nanotubes driven by heterogeneous hydrogen bonding, exhibiting positive circular dichroism (CD) and circularly polarized luminescence (CPL) signals. In contrast, the L-1-substituted isomer assembles into right-handed twisted ribbons stabilized by cooperative hydrogen bonding, displaying inverted CD and CPL responses. These structural differences can further dictate the alignment of doped achiral fluorescent dyes, resulting in morphology-dependent induced CPL with either consistent or inverted signs relative to the host. This work elucidates how subtle molecular modifications direct supramolecular architecture and chiroptical function, providing a strategy for constructing tunable luminescent nanomaterials.