Protein‐like Enwrapped Perylene Bisimide Chromophore as a Bright Microcrystalline Emitter Material. Issue 38 (12th August 2019)

• Record Type: Journal Article
• Authors: Schmidt, David; Stolte, Matthias; Süß, Jasmin; Liess, Andreas; Stepanenko, Vladimir; Würthner, Frank
• Is Part Of: Angewandte Chemie international edition. Volume 58:Issue 38(2019)
• Page Start: 13385
• Page End: 13389
• Publication Date: 2019-08-12
• Subjects: crystal engineering -- dyes -- fluorescence quantum yield -- perylene bisimides -- solid-state emitters; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201907618
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: Strongly emissive solid‐state materials are mandatory components for many emerging optoelectronic technologies, but fluorescence is often quenched in the solid state owing to strong intermolecular interactions. The design of new organic pigments, which retain their optical properties despite their high tendency to crystallize, could overcome such limitations. Herein, we show a new material with monomer‐like absorption and emission profiles as well as fluorescence quantum yields over 90 % in its crystalline solid state. The material was synthesized by attaching two bulky tris(4‐tert‐butylphenyl)phenoxy substituents at the perylene bisimide bay positions. These substituents direct a packing arrangement with full enwrapping of the chromophore and unidirectional chromophore alignment within the crystal lattice to afford optical properties that resemble those of their natural pigment counterparts, in which chromophores are rigidly embedded in protein environments. Abstract : A perylene bisimide solid‐state emitting pigment with monomer‐like absorption and emission spectra and a high fluorescence quantum yield of 90 % was synthesized through the attachment of two bulky bay substituents. The full enwrapping of the chromophore and unidirectional chromophore alignment within the crystal lattice resembles natural pigments in which chromophores are embedded in protein environments.