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| Verfasst von: | Bergner, John [VerfasserIn]  |
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| | Borstelmann, Jan [VerfasserIn] |
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| | Cavinato, Luca M. [VerfasserIn] |
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| | Fuenzalida Werner, Juan Pablo [VerfasserIn] |
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| | Walla, Christian [VerfasserIn] |
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| | Hinrichs, Heike [VerfasserIn] |
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| | Schulze, Philipp [VerfasserIn] |
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| | Rominger, Frank [VerfasserIn] |
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| | Costa, Rubén D. [VerfasserIn] |
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| | Dreuw, Andreas [VerfasserIn] |
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| | Kivala, Milan [VerfasserIn] |
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| Titel: | A conformationally stable π-expanded X-type double helicene comprising dihydropyracylene units with multistage redox behavior |
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| Verf.angabe: | John Bergner, Jan Borstelmann, Luca M. Cavinato, Juan Pablo Fuenzalida-Werner, Christian Walla, Heike Hinrichs, Philipp Schulze, Frank Rominger, Rubén D. Costa, Andreas Dreuw and Milan Kivala |
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| E-Jahr: | 2024 |
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| Jahr: | 7 February 2024 |
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| Umfang: | 6 S. |
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| Illustrationen: | Illustrationen |
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| Fussnoten: | Gesehen am 28.02.2024 |
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| Titel Quelle: | Enthalten in: Chemistry - a European journal |
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| Ort Quelle: | Weinheim : Wiley-VCH, 1995 |
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| Jahr Quelle: | 2024 |
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| Band/Heft Quelle: | 30(2024), 8 vom: Feb., Artikel-ID e202303336, Seite 1-6 |
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| ISSN Quelle: | 1521-3765 |
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| Abstract: | A pi-expanded X-type double [5]helicene comprising dihydropyracylene moieties was synthesized from commercially available acenaphthene. X-ray crystallographic analysis revealed the unique highly twisted structure of the compound resulting in the occurrence of two enantiomers which were separated by chiral HPLC, owing to their high conformational stability. The compound shows strongly bathochromically shifted UV/vis absorption and emission bands with small Stokes shift and considerable photoluminescence quantum yield and circular polarized luminescence response. The electrochemical studies revealed five facilitated reversible redox events, including three reductions and two oxidations, thus qualifying the compound as chiral multistage redox amphoter. The experimental findings are in line with the computational studies based on density functional theory pointing towards increased spatial extension of the frontier molecular orbitals over the polycyclic framework and a considerably narrowed HOMO-LUMO gap. An unprecedented X-type double helicene with pi-expanded polycyclic framework and exceptional conformational stability was realized and its enantiomers were successfully separated. Comprehensive spectroscopic and electrochemical studies in conjunction with theory identified the compound as a strong chiral fluorophore with 5-stage amphoteric redox behavior.image |
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| DOI: | doi:10.1002/chem.202303336 |
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| URL: | Bitte beachten Sie: Dies ist ein Bibliographieeintrag. Ein Volltextzugriff für Mitglieder der Universität besteht hier nur, falls für die entsprechende Zeitschrift/den entsprechenden Sammelband ein Abonnement besteht oder es sich um einen OpenAccess-Titel handelt.
kostenfrei: Volltext: https://doi.org/10.1002/chem.202303336 |
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| | kostenfrei: Volltext: https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/chem.202303336 |
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| | DOI: https://doi.org/10.1002/chem.202303336 |
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| Datenträger: | Online-Ressource |
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| Sprache: | eng |
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| Sach-SW: | helicenes |
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| | chiroptical properties |
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| | conformational stability |
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| | DISPERSION |
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| | double helicenes |
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| | ELECTRON |
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| | ENERGIES |
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| | MOLECULES |
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| | ONE HUNDRED YEARS |
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| | pyracylene |
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| | STEREOSELECTIVE SYNTHESES |
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| K10plus-PPN: | 1882052234 |
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| Verknüpfungen: | → Zeitschrift |
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A conformationally stable π-expanded X-type double helicene comprising dihydropyracylene units with multistage redox behavior / Bergner, John [VerfasserIn]; 7 February 2024 (Online-Ressource)
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