Chiral Semibuckminsterfullerene: Synthesis, Resolution, and Chiroptical Properties
A gram-scalable synthesis of C30-buckybowls derived from <b>1</b> and the first example of desymmetrization to a chiral semifullerene are presented, together with experimental and theoretically determined chiroptical and electronic properties. Chiral hemifullerenes as scaffolds for creating new ligands, receptors, sensors, and catalysts capable of stereoselective functions with remarkable configurational stability are a clear next step in the development of these curved aromatics. The optimized process enables gram-scale production of <b>1</b> and <b>2</b>, with potential for further scale-up using a modern pilot plant infrastructure, making these compounds practical for developing new materials.
Authors
- Jay S. Siegel (ORCID: https://orcid.org/0000-0002-3226-3521)
- Glenn P. A. Yap (ORCID: https://orcid.org/0000-0003-0385-387X)
- Kim K. Baldridge (ORCID: https://orcid.org/0000-0001-7171-3487)
- Justin K. Yang (ORCID: https://orcid.org/0000-0001-5785-8970)
- Marcus A. Tius (ORCID: https://orcid.org/0000-0002-7092-8993)
- Cody F. Dickinson (ORCID: https://orcid.org/0000-0003-1318-4438)
- Xiaoqi Tian (ORCID: https://orcid.org/0000-0003-4573-2208)
Institutions
- University of Hawaiʻi at Mānoa (US)
- Tianjin University (CN)
- University of Delaware (US)
- University of Hong Kong (HK)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-10-28
- DOI
- https://doi.org/10.1021/acs.orglett.5c03785
- Primary Topic
- Synthesis and Properties of Aromatic Compounds
- Type
- article
- Field-Weighted Citation Impact
- 0.00