Pyrazine-Linked End-Functionalized Helicenes: Impact of π-Extension on Frontier Orbital Localization and Chiroptical Properties
Control of chiroptical responses in π-conjugated molecules is critical for the design of chiral materials. We synthesized terminal π-extended helicenes linked by a pyrazine bridge and investigated their circular dichroism. Extension from naphthalene to tetracene decreased the S<sub>0</sub> → S<sub>1</sub> dissymmetry factors from 0.027 to nearly zero. TD-DFT calculations and our transition-moment density analysis revealed that frontier orbital localization on the helicene moiety is essential to achieving large <i>g</i> values, clarifying the origin of strong chiroptical activity.
Authors
- Takashi Hirose (ORCID: https://orcid.org/0000-0002-5351-2101)
- Zhibo Liu
- Zheng Zhang (ORCID: https://orcid.org/0009-0008-7717-5307)
Institutions
- Kyoto University (JP)
- Kyoto Bunkyo University (JP)
- Kyoto University Institute for Chemical Research
Publication Details
- Journal
- Organic Letters
- Published
- 2025-09-29
- DOI
- https://doi.org/10.1021/acs.orglett.5c03620
- Citations
- 3
- Primary Topic
- Synthesis and Properties of Aromatic Compounds
- Type
- article
- Field-Weighted Citation Impact
- 2.81