Columnar Mesomorphism of Board-Shaped Perylene, Diketopyrrolopyrrole, Isoindigo, Indigo, and Quinoxalino-Phenanthrophenazine Dyes

Chempluschem. 2021 Feb;86(2):319-339. doi: 10.1002/cplu.202100024.

Abstract

The properties of organic dyes depend as much on their intermolecular interactions as on their molecular structure. While it is generally predictable what supramolecular structure would be ideal for a specific application, the generation of specific supramolecular structures by molecular design and suitable processing methods remains to be a challenge. A versatile approach to different supramolecular structures has been the application of mesomorphism in conjunction with alignment techniques and self-assembly at interfaces. Reviewed here is the columnar mesomorphism of board-shaped dyes perylene, indigo, isoindigo, diketopyrrolopyrrole, and quinoxalinophenanthrophenazine. They generate a larger number of different supramolecular structures than conventional disc-shaped (discotic) mesogens because of their non-circular shape and directional intermolecular interactions. The mesomorphism of all but the perylene derivatives is systematically and comprehensively covered for the first time.

Keywords: board-shaped dyes; columnar mesomorphism; liquid crystals; mesophases; self-assembly.

Publication types

  • Review
  • Research Support, Non-U.S. Gov't