清华大学王梅祥团队报道了氮掺杂锯齿型芳香截锥带。相关研究成果于2025年1月2日发表在《美国化学会杂志》。

半个多世纪以来，锯齿形芳香烃带，即锯齿形碳纳米管的超短片段，因其美观的分子纳米结构和诱人的应用而在化学界引起了极大的兴趣。精确引入具有不同电负性和电子构型的杂原子，可以创建具有新颖物理和化学性质的各种杂环芳香族纳米带。

该文中，研究人员报告了从现成的氮杂杯芳烃[N]（3,5-二溴吡啶）s的多个分子内Caryl-Caryl均偶联反应合成前所未有的N掺杂锯齿型芳香带，带[N]吡咯[N]吡啶（N=6-8）。这些化合物具有全局π共轭带结构，并显示出独特的光物理和电化学性质。带[8]吡咯[8]吡啶的截锥腔被用作突出的寄主，与富勒烯形成非常稳定的2:1包封复合物。

该工作为合理设计和有效合成具有不同拓扑结构，和量身定制性质的芳香带开辟了一条新途径，这在材料和超分子化学的应用中具有不可估量的价值。

附：英文原文

Title: N-Doped Zigzag-Type Aromatic Truncated Cone Belts

Author: Jia-Hui Chen, Teng-Yu Huang, Shuo Tong, Mei-Xiang Wang

Issue&Volume: January 2, 2025

Abstract: Zigzag aromatic hydrocarbon belts, ultrashort segments of zigzag carbon nanotubes, have been fascinating in the chemistry community for more than a half century because of their aesthetically appealing molecular nanostructures and tantalizing applications. Precise introduction of heteroatoms of distinct electronegativity and electronic configuration can create various heterocyclic aromatic nanobelts with novel physical and chemical properties. Here, we report the synthesis of unprecedented N-doped zigzag-type aromatic belts, belt[n]pyrrole[n]pyridines (n = 6–8), from multiple intramolecular Caryl–Caryl homocoupling reactions of readily available azacalix[n](3,5-dibromopyridine)s. These compounds adopt globally π-conjugated belt structures and display unique photophysical and electrochemical properties. The truncated cone cavity of belt[8]pyrrole[8]pyridine was used as the outstanding host to form very stable 2:1 encapsulation complexes with fullerenes. This work opens a new avenue to the rational design and efficient synthesis of aromatic belts of distinct topological structures and tailor-made properties, which are invaluable in applications in materials and supramolecular chemistry.

DOI: 10.1021/jacs.4c11468

Source: https://pubs.acs.org/doi/abs/10.1021/jacs.4c11468