Intramolecular Energy and Solvent-Dependent Chirality Transfer within a BINOL-Perylene Hetero-Cyclophane
Please always quote using this URN: urn:nbn:de:bvb:20-opus-318818
- 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. ExcellentMultichromophoric 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.…
Author: | Guanghui Ouyang, Jessica Rühe, Yang Zhang, Mei-Jin Lin, Minghua Liu, Frank WürthnerORCiDGND |
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URN: | urn:nbn:de:bvb:20-opus-318818 |
Document Type: | Journal article |
Faculties: | Fakultät für Chemie und Pharmazie / Institut für Organische Chemie |
Language: | English |
Parent Title (English): | Angewandte Chemie International Edition |
Year of Completion: | 2022 |
Volume: | 61 |
Issue: | 31 |
Article Number: | e202206706 |
Source: | Angewandte Chemie International Edition 2022, 61(31):e202206706. DOI: 10.1002/anie.202206706 |
DOI: | https://doi.org/10.1002/anie.202206706 |
Dewey Decimal Classification: | 5 Naturwissenschaften und Mathematik / 54 Chemie / 547 Organische Chemie |
Tag: | chirality transfer; cyclophanes; energy transfer; perylene bisimide; solvent effects |
Release Date: | 2023/08/09 |
Licence (German): | CC BY: Creative-Commons-Lizenz: Namensnennung 4.0 International |