@article{OuyangRueheZhangetal.2022, author = {Ouyang, Guanghui and R{\"u}he, Jessica and Zhang, Yang and Lin, Mei-Jin and Liu, Minghua and W{\"u}rthner, Frank}, title = {Intramolecular Energy and Solvent-Dependent Chirality Transfer within a BINOL-Perylene Hetero-Cyclophane}, series = {Angewandte Chemie International Edition}, volume = {61}, journal = {Angewandte Chemie International Edition}, number = {31}, doi = {10.1002/anie.202206706}, url = {http://nbn-resolving.de/urn:nbn:de:bvb:20-opus-318818}, year = {2022}, abstract = {Multichromophoric macrocycles and cyclophanes are important supramolecular architectures for the elucidation of interchromophoric interactions originating from precise spatial organization. Herein, by combining an axially chiral binaphthol bisimide (BBI) and a bay-substituted conformationally labile twisted perylene bisimide (PBI) within a cyclophane of well-defined geometry, we report a chiral PBI hetero-cyclophane (BBI-PBI) that shows intramolecular energy and solvent-regulated chirality transfer from the BBI to the PBI subunit. Excellent spectral overlap and spatial arrangement of BBI and PBI lead to efficient excitation energy transfer and subsequent PBI emission with high quantum yield (80-98 \%) in various solvents. In contrast, chirality transfer is strongly dependent on the respective solvent as revealed by circular dichroism (CD) spectroscopy. The combination of energy and chirality transfer affords a bright red circularly polarized luminescence (CPL) from the PBI chromophore by excitation of BBI.}, language = {en} } @article{WehRueheHerbertetal.2021, author = {Weh, Manuel and R{\"u}he, Jessica and Herbert, Benedikt and Krause, Ana-Maria and W{\"u}rthner, Frank}, title = {Deracemization of Carbohelicenes by a Chiral Perylene Bisimide Cyclophane Template Catalyst}, series = {Angewandte Chemie International Edition}, volume = {60}, journal = {Angewandte Chemie International Edition}, number = {28}, doi = {10.1002/anie.202104591}, url = {http://nbn-resolving.de/urn:nbn:de:bvb:20-opus-244787}, pages = {15323 -- 15327}, year = {2021}, abstract = {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.}, language = {en} }