TY  - JOUR
A1  - Renner, Rebecca
A1  - Mahlmeister, Bernhard
A1  - Anhalt, Olga
A1  - Stolte, Matthias
A1  - Würthner, Frank
T1  - Chiral Perylene Bisimide Dyes by Interlocked Arene Substituents in the Bay Area
JF  - Chemistry - A European Journal
N2  - A series of perylene bisimide (PBI) dyes bearing various aryl substituents in 1,6,7,12 bay positions has been synthesized by Suzuki cross-coupling reaction. These molecules exhibit an exceptionally large and conformationally fixed twist angle of the PBI π-core due to the high steric congestion imparted by the aryl substituents in bay positions. Single crystal X-ray analyses of phenyl-, naphthyl- and pyrenyl-functionalized PBIs reveal interlocked π-π-stacking motifs, leading to conformational chirality and the possibility for the isolation of enantiopure atropoisomers by semipreparative HPLC. The interlocked arrangement endows these molecules with substantial racemization barriers of about 120 kJ mol\(^{−1}\) for the tetraphenyl- and tetra-2-naphthyl-substituted derivatives, which is among the highest racemization barriers for axially chiral PBIs. Variable temperature NMR studies reveal the presence of a multitude of up to fourteen conformational isomers in solution that are interconverted via smaller activation barriers of about 65 kJ mol\(^{−1}\). The redox and optical properties of these core-twisted PBIs have been characterized by cyclic voltammetry, UV/Vis/NIR and fluorescence spectroscopy and their respective atropo-enantiomers were further characterized by circular dichroism (CD) and circular polarized luminescence (CPL) spectroscopy.
KW  - Suzuki coupling
KW  - perylenebisimide dyes
KW  - circular polarized luminescence
KW  - chirality
Y1  - 2021
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-249070
VL  - 27
IS  - 46
SP  - 11997
EP  - 12006
ER  - 
TY  - JOUR
A1  - Menekse, Kaan
A1  - Renner, Rebecca
A1  - Mahlmeister, Bernhard
A1  - Stolte, Matthias
A1  - Würthner, Frank
T1  - Bowl-shaped naphthalimide-annulated corannulene as nonfullerene acceptor in organic solar cells
JF  - Organic Materials
N2  - An electron-poor bowl-shaped naphthalimide-annulated corannulene with branched alkyl residues in the imide position was synthesized by a palladium-catalyzed cross-coupling annulation sequence. This dipolar compound exhibits strong absorption in the visible range along with a low-lying LUMO level at –3.85 eV, enabling n-type charge transport in organic thin-film transistors. Furthermore, we processed inverted bulk-heterojunction solar cells in combination with the two donor polymers PCE–10 and PM6 to achieve open-circuit voltages up to 1.04 V. By using a blend of the self-assembled naphthalimide-annulated corannulene and PCE–10, we were able to obtain a power conversion efficiency of up to 2.1%, which is to the best of our knowledge the highest reported value for a corannulene-based organic solar cell to date.
KW  - Chemie
KW  - corannulene
KW  - nonfullerene acceptors
KW  - curved π-systems
KW  - bulk-heterojunction solar cells
KW  - aggregation
Y1  - 2020
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-299095
UR  - https://www.thieme-connect.com/products/ejournals/html/10.1055/s-0040-1714283
SN  - 2625-1825
VL  - 2
IS  - 3
ER  -