Access to Sondheimer-Wong Diyne-Embedded Diaza[7]helicene with High Dissymmetry Factor Via Spontaneous Valence Isomerization
The synthesis of Sondheimer-Wong diyne-fused diaza[7]helicene was achieved through spontaneous valence isomerization, which was a key step. Crystallographic analysis resolved the diaza[7]helicene's absolute configuration. The <i>P</i>,<i>P-</i> and <i>M</i>,<i>M-</i>enantiomers were separated by chiral HPLC and further characterized by CD and CPL spectroscopy. The obtained aza[7]helicene shows high dissymmetry factors with a <i>g</i><sub>abs</sub> of 0.046 (608 nm) and a <i>g</i><sub>lum</sub> of 0.0138 (693 nm). Theoretical calculation revealed that the Sondheimer-Wong diyne integration suppressed |<i><b>μ</b></i>| and enhanced |<i><b>m</b></i>| resulting in the high <i>g</i> factor.
Authors
- Wangshui Cai
- Tingting Ding (ORCID: https://orcid.org/0000-0002-4537-9451)
- Wanwan Wang (ORCID: https://orcid.org/0000-0002-0981-1382)
- Jilei Liang (ORCID: https://orcid.org/0000-0002-3262-6521)
- Guanxing Zhu
- Gang Zhang (ORCID: https://orcid.org/0000-0002-4674-7252)
- Hailong Chen (ORCID: https://orcid.org/0000-0002-1101-1990)
Institutions
- Nanjing Forestry University (CN)
- Taizhou University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-06-11
- DOI
- https://doi.org/10.1021/acs.orglett.5c01719
- Citations
- 2
- Primary Topic
- Synthesis and Properties of Aromatic Compounds
- Type
- article
- Field-Weighted Citation Impact
- 1.87