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Molecular Tweezer Based on Perylene and Crown Ether for Selective Recognition of Fullerenes
Ke Luan1, Qiao-Fen Lin1, Fang-Fang Xie1
1State 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.
Abstract:
A molecular tweezer trans-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 C60, C70, and C76. 1H 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 C60, revealing potential application for the separation of fullerenes by means of host-guest interactions.
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