Synthesis and Liquid Crystalline Properties of Unsymmetrically Substituted Naphthalenediimides with a Polar Headgroup: Effect of Amide Hydrogen Bonding and Alkyl Chain Length

Abstract

A series of new unsymmetrically substituted naphthalenediimide (NDI) moieties NDI-1 to NDI-6 were synthesized. The structures of these compounds were confirmed by means of FT-IR, 1H NMR, 13C NMR, ESI-mass and HRMS spectroscopic measurements. UV/Vis and fluorescence spectroscopy were employed to investigate the photophysical properties of the prepared compounds in solution and in the solid state. Using the onset of UV/Vis absorption, the optical band gaps were calculated. Cyclic voltammetry measurements were performed to study the electrochemical behavior and to calculate the LUMO energy levels. The thermal properties of NDI derivatives were studied by differential scanning calorimetry. The mesomorphic birefringent behavior of the NDI derivatives was investigated with polarizing optical microscopy. Among all of the studied NDI derivatives, only NDI-1, NDI-2, and NDI-3 showed liquid crystalline texture, owing to the presence of an amide linkage for H-bonding along with aromatic moieties for π–π-stacking.