期刊
ORGANIC CHEMISTRY FRONTIERS
卷 8, 期 4, 页码 727-735出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0qo01452d
关键词
-
资金
- Jiangsu Specially Appointed Professor Plan
Embedding heteroatoms in buckybowls is an effective strategy to alter their properties, with sulfur atoms in the rim and nitrogen atoms in the center allowing for tunable properties based on the state of the sulfur atoms. The electron-rich buckybowl with sulfide exhibits weak fluorescence and strong interaction with fullerene C-60, while the buckybowl with sulfonyl group shows the strongest photoluminescence and weak association behavior with fullerene C-60 due to reduced electron density.
Embedding heteroatoms in buckybowls is an effective approach to alter their electronic structures and physicochemical properties. However, buckybowls with heteroatoms situated at both the peripheral rim and the central core to modulate the properties are quite rare. Herein, we report buckybowls containing sulfur atoms at the rim and nitrogen atoms in the center with tunable properties according to the state of the sulfur atoms. When the sulfur atoms are in the form of electron-donating sulfide, the buckybowl demonstrates weak fluorescence. It shows a low oxidative potential and elevated frontier molecular orbital energy levels due to the increased electron density. The electron-rich heterobuckybowl can be chemically oxidized to generate monocations and dications with gradually planarized structures according to the oxidation state. Moreover, it can assemble with electron-deficient fullerene C-60 to form a 1 : 1 complex in toluene solution and a 2 : 1 complex in the crystalline state with strong intermolecular attractive interactions. After the oxidation of the sulfur atom to an electron-withdrawing sulfonyl group, the buckybowl shows the strongest photoluminescence in both solution and solid states in the regime of heterobuckybowls thus far. A decline in frontier molecular orbital energy levels and weak association behavior with fullerene C-60 to generate a 1 : 1 complex in toluene solution are also observed due to the reduced electron density.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据