• Supramolecular chemistry
• Naphthalenediimide
• Circular Dichroism
• Chiroptical Spectroscopy

So far, pi-conjugated molecules have been successfully applied in organic electronics. Moreover, electronic devices based on chiral molecules can be applied in circularly polarized light-based technologies and spintronics. To contribute to this interesting field, in this work we synthesised and fully characterized three new chiral naphthalene diimide derivatives bearing different functional groups: a simple alkyl chain, a carboxylic acid and an amide moiety. These compounds could self-assembly in suitable conditions resulting in chiral supramolecular structure with different opto-electronic properties. The aggregation was assessed via Absorption, Fluorescence, Circular Dichroism and Circularly Polarized Luminescence spectroscopies in mixtures of good solvents (chloroform, TCE, THF) and poor solvents (cyclohexane, MCH or water depending on the compound). To investigate the supramolecular properties in solid state, the compounds were analysed as powder, crystals and thin films. We found that the NDI bearing two alkyl chains showed aggregation with increasing volume fraction of water, and showed high anisotropy factor g in thin films. The acid appended NDI could self-assemble in mixtures chloroform/MCH 5/95, showing an excimer-like almost-white emission band.