Premium
Diketopyrrolopyrrole Columnar Liquid‐Crystalline Assembly Directed by Quadruple Hydrogen Bonds
Author(s) -
Soberats Bartolome,
Hecht Markus,
Würthner Frank
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201705137
Subject(s) - hydrogen bond , crystallography , columnar phase , supramolecular chemistry , chromophore , steric effects , materials science , self assembly , supramolecular assembly , liquid crystalline , molecule , chemistry , nanotechnology , crystal structure , liquid crystal , stereochemistry , photochemistry , organic chemistry , optoelectronics
A diketopyrrolopyrrole (DPP) dye self‐assembles via a unique hydrogen‐bonding motif into an unprecedented columnar liquid‐crystalline (LC) structure. X‐ray and polarized FTIR experiments reveal that the DPPs organize into a one‐dimensional assembly with the chromophores oriented parallel to the columnar axis. This columnar structure is composed of two π–π‐stacked DPP dimers with mirror‐image configurations that stack alternately through quadruple hydrogen bonding by 90° rotation. This exotic packing is dictated by the complementarity between H‐bonds and the steric demands of the wedge‐shaped groups attached at the core. This novel LC supramolecular material opens a new avenue of research on DPP dye assemblies with photofunctional properties tailored by H‐bonding networks.