Chen Xu-Lang, Yu Si-Qian, Zheng Zi-You, Cheng Zhao-Yi, Chen An-Na, Liang Jia-Qi, Sun Xin, Zheng Chunyang, Huang Xiaohuan, Gong Han-Yuan
College of Chemistry and Chemical Engineering, Hubei Key Laboratory of Pollutant Analysis and Reuse Technology, Hubei Normal University Huangshi 435002 P. R. China
College of Chemistry, Beijing Normal University No. 19, Xin Jie Kou Wai St, Hai Dian District Beijing 100875 P. R. China
Chem Sci. 2025 Mar 25;16(17):7537-7543. doi: 10.1039/d5sc00988j. eCollection 2025 Apr 30.
Bowl-shaped polycyclic aromatic hydrocarbons (PAHs), or buckybowls, are renowned for their unique structures and physicochemical properties, making them promising fragments for functional materials. While well-known examples like corannulene and sumanene demonstrate their potential, synthetic challenges have limited the development of other fullerene fragments. Recent advancements, particularly the incorporation of heteroatoms, have expanded the structural diversity of buckybowls. In this study, we report the synthesis of a novel nitrogen-containing buckybowl (1) using the core-periphery strategy that connects two half-bowls a single carbon-carbon bond, followed by peripheral stitching. This molecule features two nitrogen atoms within its bowl-shaped framework, representing a significant advancement in structural diversity. Compound 1 exhibits intense red emission with high color purity and quantum yield in solution. Additionally, it possesses adaptive curvature adjustment and shows excellent binding affinity to the curved PAH corannulene, the spherical PAH C, as well as the planar PAH pyrene. These versatile assembly capabilities highlight its potential applications in supramolecular chemistry and materials science, paving the way for advancements in molecular electronics and photonics.
碗状多环芳烃（PAHs），即巴基碗，以其独特的结构和物理化学性质而闻名，使其成为功能材料的有前景的片段。虽然像碗烯和苏曼烯这样的知名例子展示了它们的潜力，但合成挑战限制了其他富勒烯片段的发展。最近的进展，特别是杂原子的引入，扩大了巴基碗的结构多样性。在本研究中，我们报告了一种新型含氮巴基碗（1）的合成，采用核心-外围策略，通过单个碳-碳键连接两个半碗，然后进行外围缝合。该分子在其碗状框架内具有两个氮原子，代表了结构多样性的重大进展。化合物1在溶液中表现出强烈的红色发射，具有高色纯度和量子产率。此外，它具有自适应曲率调节能力，并对弯曲的PAH碗烯、球形PAH C以及平面PAH芘表现出优异的结合亲和力。这些多功能的组装能力突出了其在超分子化学和材料科学中的潜在应用，为分子电子学和光子学的进步铺平了道路。
