TY  - JOUR
A1  - Weh, Manuel
A1  - Rühe, Jessica
A1  - Herbert, Benedikt
A1  - Krause, Ana‐Maria
A1  - Würthner, Frank
T1  - Deracemization of Carbohelicenes by a Chiral Perylene Bisimide Cyclophane Template Catalyst
JF  - Angewandte Chemie International Edition
N2  - Deracemization describes the conversion of a racemic mixture of a chiral molecule into an enantioenriched mixture or an enantiopure compound without structural modifications. Herein, we report an inherently chiral perylene bisimide (PBI) cyclophane whose chiral pocket is capable of transforming a racemic mixture of [5]‐helicene into an enantioenriched mixture with an enantiomeric excess of 66 %. UV/Vis and fluorescence titration studies reveal this cyclophane host composed of two helically twisted PBI dyes has high binding affinities for the respective homochiral carbohelicene guests, with outstanding binding constants of up to 3.9×10\(^{10}\) m\(^{-1}\) for [4]‐helicene. 2D NMR studies and single‐crystal X‐ray analysis demonstrate that the observed strong and enantioselective binding of homochiral carbohelicenes and the successful template‐catalyzed deracemization of [5]‐helicene can be explained by the enzyme‐like perfect shape complementarity of the macrocyclic supramolecular host.
KW  - chirality transfer
KW  - cyclophanes
KW  - deracemization
KW  - dyes/pigments
KW  - template catalysis
Y1  - 2021
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-244787
VL  - 60
IS  - 28
SP  - 15323
EP  - 15327
ER  - 
TY  - JOUR
A1  - Ferger, Matthias
A1  - Berger, Sarina M.
A1  - Rauch, Florian
A1  - Schönitz, Markus
A1  - Rühe, Jessica
A1  - Krebs, Johannes
A1  - Friedrich, Alexandra
A1  - Marder, Todd B.
T1  - Synthesis of Highly Functionalizable Symmetrically and Unsymmetrically Substituted Triarylboranes from Bench-Stable Boron Precursors
JF  - Chemistry—A European Journal
N2  - A novel and convenient methodology for the one-pot synthesis of sterically congested triarylboranes by using bench-stable aryltrifluoroborates as the boron source is reported. This procedure gives systematic access to symmetrically and unsymmetrically substituted triarylboranes of the types BAr\(_{2}\)Ar’ and BArAr'Ar’’, respectively. Three unsymmetrically substituted triarylboranes as well as their iridium-catalyzed C−H borylation products are reported. These borylated triarylboranes contain one to three positions that can subsequently be orthogonally functionalized in follow-up reactions, such as Suzuki-Miyaura cross-couplings or Sonogashira couplings.
KW  - synthetic methods
KW  - boranes
KW  - borylation
KW  - chromophore
KW  - functionalization
Y1  - 2021
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-256827
VL  - 27
IS  - 35
ER  - 
TY  - JOUR
A1  - Berger, Sarina M.
A1  - Rühe, Jessica
A1  - Schwarzmann, Johannes
A1  - Phillipps, Alexandra
A1  - Richard, Ann-Katrin
A1  - Ferger, Matthias
A1  - Krummenacher, Ivo
A1  - Tumir, Lidija-Marija
A1  - Ban, Željka
A1  - Crnolatac, Ivo
A1  - Majhen, Dragomira
A1  - Barišić, Ivan
A1  - Piantanida, Ivo
A1  - Schleier, Domenik
A1  - Griesbeck, Stefanie
A1  - Friedrich, Alexandra
A1  - Braunschweig, Holger
A1  - Marder, Todd B.
T1  - Bithiophene-Cored, mono-, bis-, and tris-(Trimethylammonium)-Substituted, bis-Triarylborane Chromophores: Effect of the Number and Position of Charges on Cell Imaging and DNA/RNA Sensing
JF  - Chemistry—A European Journal
N2  - The synthesis, photophysical, and electrochemical properties of selectively mono-, bis- and tris-dimethylamino- and trimethylammonium-substituted bis-triarylborane bithiophene chromophores are presented along with the water solubility and singlet oxygen sensitizing efficiency of the cationic compounds Cat\(^{1+}\), Cat\(^{2+}\), Cat(i)\(^{2+}\), and Cat\(^{3+}\). Comparison with the mono-triarylboranes reveals the large influence of the bridging unit on the properties of the bis-triarylboranes, especially those of the cationic compounds. Based on these preliminary investigations, the interactions of Cat\(^{1+}\), Cat\(^{2+}\), Cat(i)\(^{2+}\), and Cat\(^{3+}\) with DNA, RNA, and DNApore were investigated in buffered solutions. The same compounds were investigated for their ability to enter and localize within organelles of human lung carcinoma (A549) and normal lung (WI38) cells showing that not only the number of charges but also their distribution over the chromophore influences interactions and staining properties.
KW  - singlet oxygen
KW  - boron
KW  - bioimaging
KW  - luminescence
KW  - nucleic acid
Y1  - 2021
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-256963
VL  - 27
IS  - 56
ER  -