A limited number of poly(ethylene oxide)-substituted perylene bisimides, some of which are equipped with terpyridine ligands for transition-metal coordination (see structure), combine different types of noncovalent interactions to yield optoelectronically active organic materials with different types of supramolecular morphologies.

Linking covalently flexible polymer segments to a donor-acceptor-donor triad is an efficient way to gain control over the formation of materials with well-defined lamellar mesostructure of interest for organic photovoltaics.

Functional π-conjugated molecules are relevant for the preparation of new organic electronic materials with improved performance. However, their synthesis is often rendered difficult by their inherently low solubility, and the permanent attachment of solubilizing groups may change the properties of the material. Here, we introduced the chlorendylimidyl moiety as a new temporary protecting group for the straightforward large-scale synthesis of protected quarter-, sexi-, octathiophene, and perylene bisimide diamine and dicarboxylic acid derivatives. The obtained chlorendylimides and chlorendylimidyl active esters were highly soluble in organic solvents, and optical spectroscopy confirmed the low tendency of the compounds to aggregate in solution. At the same time, they could be conveniently purified by recrystallization or precipitation. Single-crystal X-ray structures obtained for most compounds showed supramolecular motifs highlighting the role of the rigid, polychlorinated chlorendyl moieties in their crystallization. The obtained protected diamine and dicarboxylic acid derivatives were easily deprotected and converted into various amide-substituted oligothiophenes and perylene bisimides that are of interest as new functional materials for organic electronic thin film or nanowire devices.

Eine begrenzte Zahl Polyethylenoxid‐substituierter Perylenbisimide, die wahlweise mit Terpyridin‐Liganden für eine Metallkoordination funktionalisiert sind (siehe Beispielstruktur), kombiniert verschiedene nichtkovalente Wechselwirkungen und kann so in eine Vielzahl von optoelektronisch aktiven, organischen Materialien mit unterschiedlichen Überstrukturen verarbeitet werden.