Synthesis of Carborane-Functionalized Macrocycles: Bond-Angle-Modulated Cavities and Cation-Mediated Assembly

作者：Ying‐Zheng Ren, Nian Si, Pengfei Liu, Hao-Hui Xie, Wenchao Zhang, Peng‐Fei Cui · 发表于：Organic Letters · 年份：2025 · DOI：10.1021/acs.orglett.5c04579 · 被引用次数：3 · 研究领域：Boron Compounds in Chemistry、Supramolecular Chemistry and Complexes、Surface Chemistry and Catalysis

Herein, a novel synthetic strategy for macrocycles based on a three-dimensional carborane skeleton via a cyclization reaction was developed. Further substrate scope experiments confirm that this strategy possesses excellent reaction compatibility. In addition, the cavity size of the macrocycle can be regulated by the bonding angle, in which the size of the macrocycle cavity formed by para -carborane (180°) is larger than that formed by meta -carborane (120°). More importantly, when a pyridine group is introduced into this type of macrocycle, nanotubes can be constructed through the coordination modes of [N···Ag + ···N] and [N···I + ···N]. The host–guest properties of the macrocycles are also explored to show the specific encapsulation of dichloromethane molecules through van der Waals forces. This work significantly enriches the structural diversity of supramolecular macrocycles and develops unique host–guest properties of the carborane-based macrocycles.