The delayed box: biphenyl bisimide cyclophane, a supramolecular nano-environment for the efficient generation of delayed fluorescence
Please always quote using this URN: urn:nbn:de:bvb:20-opus-370385
- Activating delayed fluorescence emission in a dilute solution via a non-covalent approach is a formidable challenge. In this report, we propose a strategy for efficient delayed fluorescence generation in dilute solution using a non-covalent approach via supramolecularly engineered cyclophane-based nanoenvironments that provide sufficient binding strength to π-conjugated guests and that can stabilize triplet excitons by reducing vibrational dissipation and lowering the singlet–triplet energy gap for efficient delayed fluorescence emission.Activating delayed fluorescence emission in a dilute solution via a non-covalent approach is a formidable challenge. In this report, we propose a strategy for efficient delayed fluorescence generation in dilute solution using a non-covalent approach via supramolecularly engineered cyclophane-based nanoenvironments that provide sufficient binding strength to π-conjugated guests and that can stabilize triplet excitons by reducing vibrational dissipation and lowering the singlet–triplet energy gap for efficient delayed fluorescence emission. Toward this goal, a novel biphenyl bisimide-derived cyclophane is introduced as an electron-deficient and efficient triplet-generating host. Upon encapsulation of various carbazole-derived guests inside the nanocavity of this cyclophane, emissive charge transfer (CT) states close to the triplet energy level of the biphenyl bisimide are generated. The experimental results of host–guest studies manifest high association constants up to 10\(^4\) M\(^{–1}\) as the prerequisite for inclusion complex formation, the generation of emissive CT states, and triplet-state stabilization in a diluted solution state. By means of different carbazole guest molecules, we could realize tunable delayed fluorescence emission in this carbazole-encapsulated biphenyl bisimide cyclophane in methylcyclohexane/carbon tetrachloride solutions with a quantum yield (QY) of up to 15.6%. Crystal structure analyses and solid-state photophysical studies validate the conclusions from our solution studies and provide insights into the delayed fluorescence emission mechanism.…
Author: | Swadhin Garain, Kazutaka ShoyamaORCiD, Lea-Marleen Ginder, Menyhárt SárosiORCiD, Frank WürthnerORCiD |
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URN: | urn:nbn:de:bvb:20-opus-370385 |
Document Type: | Journal article |
Faculties: | Fakultät für Chemie und Pharmazie / Institut für Organische Chemie |
Language: | English |
Parent Title (English): | Journal of the American Chemical Society |
ISSN: | 0002-7863 |
Year of Completion: | 2024 |
Volume: | 146 |
Issue: | 31 |
Pagenumber: | 22056-22063 |
Source: | Journal of the American Chemical Society (2024) 146:31, 22056-22063. https.doi.org/10.1021/jacs.4c07730 |
DOI: | https://doi.org/10.1021/jacs.4c07730 |
Dewey Decimal Classification: | 5 Naturwissenschaften und Mathematik / 54 Chemie / 547 Organische Chemie |
Tag: | aromatic compounds; complexation; encapsulation; fluorescence; hydrocarbons |
Release Date: | 2024/08/09 |
EU-Project number / Contract (GA) number: | 787937 |
OpenAIRE: | OpenAIRE |
Licence (German): | CC BY-NC-ND: Creative-Commons-Lizenz: Namensnennung, Nicht kommerziell, Keine Bearbeitungen 4.0 International |