<i>C</i><sub>2</sub>-Symmetric Perylene-Embedded Double [5]Helicenes
High quantum yields and dissymmetry factors are key to enhancing the chiroptical properties of [<i>n</i>]helicene-functionalized polycyclic aromatic hydrocarbons for the development of circularly polarized materials. In a two-step synthesis, a <i>C</i><sub>2</sub>-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<sup>-1</sup>, 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 <i>g</i><sub>abs</sub> of up to 8.8 × 10<sup>-3</sup>, and a <i>g</i><sub>lum</sub> of 0.7 × 10<sup>-3</sup>.
Authors
- Asim Kumar Swain (ORCID: https://orcid.org/0000-0002-3747-9057)
- Michael Mastalerz (ORCID: https://orcid.org/0000-0003-3231-4816)
- Frank Röminger
Institutions
- Heidelberg University (DE)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-07-24
- DOI
- https://doi.org/10.1021/acs.orglett.5c02745
- Citations
- 4
- Primary Topic
- Synthesis and Properties of Aromatic Compounds
- Type
- article
- Field-Weighted Citation Impact
- 3.74
Funders
- Deutsche Forschungsgemeinschaft
- Ministerium für Wissenschaft, Forschung und Kunst Baden-Württemberg