title: Hydrogen bond-directed aggregation of diazadibenzoperylene dyes in low-polarity solvents and the solid state.
abstract: The formation of complex superstructures via hydrogen bonding of two ditopic building blocks, diazadibenzoperylenes 1a,b and isophthalic acid 2, has been investigated. It was found that only the phenoxy-substituted diazadibenzoperylene 1a forms extended assemblies with 2 in complexes of a 1:1 stoichiometry, whereas for the 4-tert-butylphenoxy-substituted analogue 1b, no indications for superstructure formation with 2 were found. The different behavior is explained by the presence of additional pi-pi interactions, which are only observed for [1a x 2], as revealed by concentration-dependent optical absorption and fluorescence spectroscopy. Based on variable temperature x-ray diffraction studies, a lamellar structure for [1a x 2] is proposed that takes into account the concept of microphase-segregation.
authors.affiliation: Organische Chemie II, Universität Ulm, Albert-Einstein-Allee 11, D-89081 Ulm, Germany.
authors.forename: Armin
authors.initials: A
authors.lastname: Sautter
authors.forename: Christoph
authors.initials: C
authors.lastname: Thalacker
authors.forename: Bernd
authors.initials: B
authors.lastname: Heise
authors.forename: Frank
authors.initials: F
authors.lastname: Wurthner
mesh_terms: D004396:Coloring Agents / Q000737:chemistry*; D003510:Cyclohexanes / Q000737:chemistry; D004305:Dose-Response Relationship, Drug; D004307:Dose-Response Relationship, Radiation; D006860:Hydrogen Bonding; D046911:Macromolecular Substances; D008956:Models, Chemical; D010569:Perylene / Q000031:analogs & derivatives* / Q000737:chemistry*; D013050:Spectrometry, Fluorescence; D013696:Temperature; D014466:Ultraviolet Rays; D014961:X-Ray Diffraction
chemical_list: D004396:Coloring Agents; D003510:Cyclohexanes; D046911:Macromolecular Substances; C006706:benzoperylene; D010569:Perylene