TY  - JOUR
A1  - Ouyang, Guanghui
A1  - Rühe, Jessica
A1  - Zhang, Yang
A1  - Lin, Mei-Jin
A1  - Liu, Minghua
A1  - Würthner, Frank
T1  - Intramolecular Energy and Solvent-Dependent Chirality Transfer within a BINOL-Perylene Hetero-Cyclophane
JF  - Angewandte Chemie International Edition
N2  - 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.
KW  - chirality transfer
KW  - solvent effects
KW  - perylene bisimide
KW  - energy transfer
KW  - cyclophanes
Y1  - 2022
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-318818
VL  - 61
IS  - 31
ER  - 
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  -