Effects of π-Extended Aromatic Fragments on Tris(hexa-<i>peri</i>-hexabenzocoronenyl)methyl Radical and Cation: Synthesis, Radical Transformation, and Reactivity Insights
Neutral organic radicals have attracted interest for their stability and redox activity. We synthesized π-extended triarylmethanol (<b>1-OH</b>) with three HBC units, which undergoes SnCl<sub>2</sub>-mediated radical transformation into nanographenes. Protonation with trifluoroacetic acid forms a carbocation (<b>1</b><sup>+</sup>) that rapidly reverts to <b>1-OH</b> in air, reflecting the destabilizing effect of π extension. These findings reveal how extended aromatic frameworks influence radical and cation stability, offering guidance for the design of 3D nanographene-based materials.
Authors
- Han‐Yuan Gong (ORCID: https://orcid.org/0000-0003-4168-7657)
- Tongling Liang (ORCID: https://orcid.org/0000-0002-0669-9751)
- Aijiao Guan (ORCID: https://orcid.org/0000-0002-4572-610X)
- Xu‐Lang Chen
- Qian Li (ORCID: https://orcid.org/0000-0003-3366-3858)
- Xin Sun (ORCID: https://orcid.org/0000-0001-7941-7113)
- Junfeng Xiang (ORCID: https://orcid.org/0000-0002-2101-1409)
- Jiaqi Liang (ORCID: https://orcid.org/0000-0002-3796-9785)
- Dan‐Yang Wang (ORCID: https://orcid.org/0000-0003-0163-5617)
- Xiang Hao (ORCID: https://orcid.org/0000-0002-5525-2649)
- Jinku Bai
Institutions
- Chinese Academy of Sciences (CN)
- Beijing Normal University (CN)
- Chengdu University of Technology (CN)
- Beijing Academy of Social Sciences (CN)
- CAS Key Laboratory of Urban Pollutant Conversion (CN)
- Hubei Normal University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-09-01
- DOI
- https://doi.org/10.1021/acs.orglett.5c03300
- Citations
- 2
- Primary Topic
- Synthesis and Properties of Aromatic Compounds
- Type
- article
- Field-Weighted Citation Impact
- 1.87
Funders
- National Natural Science Foundation of China
- Beijing Municipal Commission of Education
- Recruitment Program of Global Experts
- Fundamental Research Funds for the Central Universities