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.

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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
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article

Chiral Semibuckminsterfullerene: Synthesis, Resolution, and Chiroptical Properties

Jay S. Siegel, Glenn P. A. Yap, Kim K. Baldridge, Justin K. Yang et al.
Organic Letters
Synthesis and Properties of Aromatic Compounds
article

Chiral Semibuckminsterfullerene: Synthesis, Resolution, and Chiroptical Properties

Jay S. Siegel, Glenn P. A. Yap, Kim K. Baldridge, Justin K. Yang, Marcus A. Tius, Cody F. Dickinson, Xiaoqi Tian
article en

Abstract

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.

Organic LettersVol. 27(44)
University of Hawaiʻi at Mānoa (US), Tianjin University (CN), University of Delaware (US), University of Hong Kong (HK)
Openalex Percentile: Top 76%
Synthesis and Properties of Aromatic Compounds
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