基于苝和冠醚的分子镊子对富勒烯的选择性识别
Molecular Tweezer Based on Perylene and Crown Ether for Selective Recognition of Fullerenes.
作者信息
Luan Ke, Lin Qiao-Fen, Xie Fang-Fang, Wang Yu, Li Yun-Fei, Wang Lu, Deng Lin-Long, Xie Su-Yuan, Zheng Lan-Sun
机构信息
State Key Lab for Physical Chemistry of Solid Surfaces, Collaborative Innovation Center of Chemistry for Energy Materials, Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China.
Pen-Tung Sah Institute of Micro-Nano Science and Technology, Xiamen University, Xiamen 361005, China.
出版信息
ACS Omega. 2022 Aug 24;7(35):31442-31447. doi: 10.1021/acsomega.2c03860. eCollection 2022 Sep 6.
A molecular tweezer -di(perylene-3-ylmethanaminobenzo)-18-crown-6 (DP-18C6) incorporating two perylene subunits in a single crown ether core was designed and synthesized as a host for fullerenes. Through the cooperative effect of the perylene subunits and the crown ether moiety, DP-18C6 can efficiently recognize fullerenes including C, C, and C. H NMR titration and fluorescence titration experiments demonstrated that DP-18C6 can effectively grasp the fullerene molecule to form a 1:1 host-guest complex. Density functional theory calculations revealed the presence of intermolecular π-π interactions between the perylene subunits of DP-18C6 and the fullerene molecule. More importantly, DP-18C6 exhibited remarkably high binding selectivity for higher fullerenes over C, revealing potential application for the separation of fullerenes by means of host-guest interactions.
设计并合成了一种分子钳——二（苝-3-基甲基氨基苯）-18-冠-6（DP-18C6），其在单个冠醚核心中包含两个苝亚基，用作富勒烯的主体。通过苝亚基和冠醚部分的协同作用，DP-18C6能够有效识别包括C、C和C在内的富勒烯。1H NMR滴定和荧光滴定实验表明，DP-18C6能够有效地捕获富勒烯分子，形成1:1的主客体复合物。密度泛函理论计算揭示了DP-18C6的苝亚基与富勒烯分子之间存在分子间π-π相互作用。更重要的是，DP-18C6对更高的富勒烯表现出比对C显著更高的结合选择性，揭示了通过主客体相互作用分离富勒烯的潜在应用。
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