Influence of hydrogen bonds and π–π stacking on the self-assembly of aryldipyrrolidones

Abstract

We report on the self-assembly behaviour in solution and in the solid-state of two newly designed bisdendronized aryldipyrrolidone (BDP and NDP) dyes with two free N–H groups at the lactam positions. Interestingly, while the naphthalene-based NDP self-assembles via π–π-stacking to form conventional columnar liquid-crystalline (LC) assemblies, the smaller benzene-based BDP forms unconventional columnar LC phases with the dyes parallel to the columnar axis, via hydrogen-bonding interactions. This work presents new design principles to modulate hydrogen bonding in dye materials with potential application in optoelectronics.