C2-symmetric perylene-embedded double [5]helicenes
High quantum yields and dissymmetry factors are key to enhancing the chiroptical properties of [n]helicene-functionalized polycyclic aromatic hydrocarbons for the development of circularly polarized materials. In a two-step synthesis, a C2-symmetric perylene-embedded double [5]helicene was obtained...
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| Hauptverfasser: | , , |
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| Dokumenttyp: | Article (Journal) |
| Sprache: | Englisch |
| Veröffentlicht: |
8 August 2025
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| In: |
Organic letters
Year: 2025, Jahrgang: 27, Heft: 31, Pages: 8770-8775 |
| ISSN: | 1523-7052 |
| DOI: | 10.1021/acs.orglett.5c02745 |
| Online-Zugang: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1021/acs.orglett.5c02745 Verlag, lizenzpflichtig, Volltext: https://pubs.acs.org/doi/10.1021/acs.orglett.5c02745 
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| Verfasserangaben: | Asim Swain, Frank Rominger, and Michael Mastalerz |
| Zusammenfassung: | High quantum yields and dissymmetry factors are key to enhancing the chiroptical properties of [n]helicene-functionalized polycyclic aromatic hydrocarbons for the development of circularly polarized materials. In a two-step synthesis, a C2-symmetric perylene-embedded double [5]helicene was obtained through Suzuki-Miyaura cross-coupling and base-catalyzed condensation. With a configurational stability of 23 kcal mol-1, the short-lived enantiomers were separated using chiral HPLC. Compared to pristine [5]helicene, the compound shows enhanced (chir)optical properties with a quantum yield of 0.7, a gabs of up to 8.8 × 10-3, and a glum of 0.7 × 10-3. |
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| Beschreibung: | Online verfügbar: 24. Juli 2025 Im Totel erscheint die 2 tiefgestellt Gesehen am 28.11.2025 |
| Beschreibung: | Online Resource |
| ISSN: | 1523-7052 |
| DOI: | 10.1021/acs.orglett.5c02745 |