Diketopyrrolopyrrole Columnar Liquid‐Crystalline Assembly Directed by Quadruple Hydrogen Bonds. (24th July 2017)

• Record Type: Journal Article
• Authors: Soberats, Bartolome; Hecht, Markus; Würthner, Frank
• Is Part Of: Angewandte Chemie. Volume 129:Number 36(2017)
• Page Start: 10911
• Page End: 10914
• Publication Date: 2017-07-24
• Subjects: Diketopyrrolopyrrole -- Farbstoffe/Pigmente -- Flüssigkristalle -- Selbstorganisation -- Wasserstoffbrücken; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201705137
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: 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.