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Molecular Tweezer Based on Perylene and Crown Ether for Selective Recognition of Fullerenes.

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.

SUBMITTER: Luan K

PROVIDER: S-EPMC9453932 | biostudies-literature | 2022 Sep

REPOSITORIES: biostudies-literature

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Molecular Tweezer Based on Perylene and Crown Ether for Selective Recognition of Fullerenes.

Luan Ke K Lin Qiao-Fen QF Xie Fang-Fang FF Wang Yu Y Li Yun-Fei YF Wang Lu L Deng Lin-Long LL Xie Su-Yuan SY Zheng Lan-Sun LS

ACS omega 20220824 35

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 effe ...[more]

PMID: 36092566

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