2025-07-10 理化学研究所,名古屋大学
本研究で開発したカーボンナノベルトの一挙多官能基化反応
＜関連情報＞
- https://www.riken.jp/press/2025/20250710_1/index.html
- https://onlinelibrary.wiley.com/doi/10.1002/anie.202510544
(6,6)カーボンナノベルトの12重脱芳香族エステル化反応 Twelvefold Dearomative Esterification of (6,6)Carbon Nanobelt
Tsubasa Okumura, Daiki Imoto, Yuri Arachi, Prof. Dr. Akiko Yagi, Dr. Takehisa Maekawa, Prof. Dr. Kenichiro Itami
Angewandte Chemie International Edition Published: 06 July 2025
DOI:https://doi.org/10.1002/anie.202510544
Abstract
Carbon nanobelts (CNBs), cyclic aromatic hydrocarbons with belt-shaped topologies, have growing interest as structurally unique and optoelectronically promising nanocarbons. Yet, strategies for their direct and site-selective functionalization remain scarce. Here, we report a magnesium-mediated, multifold dearomative esterification of (6,6)CNB, enabling the installation of twelve ester groups in a single transformation. Single-crystal X-ray structural analysis revealed regioselective dearomatization patterns, whereas mechanistic studies uncovered a radical-driven pathway involving oxyiminium intermediate generated in situ from alkyl chloroformates and amide solvents. Computational analysis further indicated that strain release in the CNB framework drives the high degree of functionalization. This methodology not only expands the synthetic toolbox for aromatic nanobelts but also allows tunable modulation of their host–guest properties via enhanced conformational flexibility.
