TY  - JOUR
A1  - Farrell, Jeffrey  M.
A1  - Grande, Vincenzo
A1  - Schmidt, David
A1  - Würthner, Frank
T1  - A Highly Warped Heptagon-Containing sp\(^2\) Carbon Scaffold via Vinylnaphthyl π-Extension
JF  - Angewandte Chemie International Edition
N2  - A new strategy is demonstrated for the synthesis of warped, negatively curved, all‐sp\(^2\)‐carbon π‐scaffolds. Multifold C−C coupling reactions are used to transform a polyaromatic borinic acid into a saddle‐shaped polyaromatic hydrocarbon (2 ) bearing two heptagonal rings. Notably, this Schwarzite substructure is synthesized in only two steps from an unfunctionalized alkene. A highly warped structure of 2 was revealed by X‐ray crystallographic studies and pronounced flexibility of this π‐scaffold was ascertained by experimental and computational studies. Compound 2 exhibits excellent solubility, visible range absorption and fluorescence, and readily undergoes two reversible one‐electron oxidations at mild potentials.
KW  - arenes
KW  - carbon
KW  - C-C coupling
KW  - curvature
KW  - polycyclic aromatic hydrocarbons
Y1  - 2019
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-206682
VL  - 58
IS  - 46
ER  - 
TY  - JOUR
A1  - Schmidt, David
A1  - Stolte, Matthias
A1  - Süß, Jasmin
A1  - Liess, Dr. Andreas
A1  - Stepanenko, Vladimir
A1  - Würthner, Frank
T1  - Protein-like enwrapped perylene bisimide chromophore as bright microcrystalline emitter material
JF  - Angewandte Chemie International Edition
N2  - 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.
KW  - cristal engeneering
KW  - dyes
KW  - flourescence quantum yield
KW  - perylene bisimides
KW  - solid-state emitters
Y1  - 2019
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-204809
VL  - 58
IS  - 38
ER  - 
TY  - JOUR
A1  - Wen, Xinbo
A1  - Nowak-Król, Agnieszka
A1  - Nagler, Oliver
A1  - Kraus, Felix
A1  - Zhu, Na
A1  - Zheng, Nan
A1  - Müller, Matthias
A1  - Schmidt, David
A1  - Xie, Zengqi
A1  - Würthner, Frank
T1  - Tetrahydroxy-perylene bisimide embedded in zinc oxide thin film as electron transporting layer for high performance non-fullerene organic solar cells
JF  - Angewandte Chemie International Edition
N2  - By introduction of four hydroxy (HO) groups into the two perylene bisimide (PBI) bay areas, new HO‐PBI ligands were obtained which upon deprotonation can complex ZnII ions and photosensitize semiconductive zinc oxide thin films. Such coordination is beneficial for dispersing PBI photosensitizer molecules evenly into metal oxide films to fabricate organic–inorganic hybrid interlayers for organic solar cells. Supported by the photoconductive effect of the ZnO:HO‐PBI hybrid interlayers, improved electron collection and transportation is achieved in fullerene and non‐fullerene polymer solar cell devices, leading to remarkable power conversion efficiencies of up to 15.95 % for a non‐fullerene based organic solar cell.
KW  - hydroxylation
KW  - metal complexenes
KW  - perylene bisimide
KW  - photoconductive interlayer
KW  - solar cells
Y1  - 2019
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-204723
VL  - 58
IS  - 37
ER  -