Catching Fullerenes: Synthesis of Molecular Nanogloves

Herein, we report the synthesis of a new series of rigid, all meta-phenylene, conjugated deep-cavity molecules, displaying high binding affinity towards buckyballs. A facile synthetic approach with an overall combined yield of approximately 53% in the last two steps has been developed using a templating strategy that combines the general structure of resorcin[4]arene and [12]cyclo-meta-phenylene. These two moieties are covalently linked via four acetal bonds, resulting in a glove-like architecture. <sup>1</sup>H NMR titration experiments reveal fullerene binding affinities (K<sub>a</sub>) exceeding ≥10<sup>6</sup> M<sup>-1</sup>. The size complementarity between fullerenes and these scaffolds maximizes CH⋯π and π⋯π interactions, and their host:guest adduct resembles a ball in a glove, hence their name as nanogloves. Fullerene recognition is tested by suspending carbon soot in a solution of nanoglove in 1,1,2,2-tetrachloroethane, where more than a dozen fullerenes are observed, ranging from C<sub>60</sub> to C<sub>96</sub>.

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Publication Details

Journal
Angewandte Chemie International Edition
Published
2025-05-01
DOI
https://doi.org/10.1002/anie.202505083
Citations
4
Primary Topic
Fullerene Chemistry and Applications
Type
article
Field-Weighted Citation Impact
3.74

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article

Catching Fullerenes: Synthesis of Molecular Nanogloves

Victor M. Espinoza Castro, M. Saeed Mirzaei, Neileth Johanna Stand Figueroa, Yu‐Sheng Chen et al.
4 citations
Angewandte Chemie International Edition
Fullerene Chemistry and Applications
3.74
article

Catching Fullerenes: Synthesis of Molecular Nanogloves

Victor M. Espinoza Castro, M. Saeed Mirzaei, Neileth Johanna Stand Figueroa, Yu‐Sheng Chen, Tieyan Chang, Xiangquan Hu, Saber Mirzaei, Natalia I. González-Pech, Ying‐Pin Chen, Hormoz Khosravi, Raúl Hernández Sánchez, Xu Wang, Gabriella Prieto Ríos
article en
4 citations

Abstract

Herein, we report the synthesis of a new series of rigid, all meta-phenylene, conjugated deep-cavity molecules, displaying high binding affinity towards buckyballs. A facile synthetic approach with an overall combined yield of approximately 53% in the last two steps has been developed using a templating strategy that combines the general structure of resorcin[4]arene and [12]cyclo-meta-phenylene. These two moieties are covalently linked via four acetal bonds, resulting in a glove-like architecture. <sup>1</sup>H NMR titration experiments reveal fullerene binding affinities (K<sub>a</sub>) exceeding ≥10<sup>6</sup> M<sup>-1</sup>. The size complementarity between fullerenes and these scaffolds maximizes CH⋯π and π⋯π interactions, and their host:guest adduct resembles a ball in a glove, hence their name as nanogloves. Fullerene recognition is tested by suspending carbon soot in a solution of nanoglove in 1,1,2,2-tetrachloroethane, where more than a dozen fullerenes are observed, ranging from C<sub>60</sub> to C<sub>96</sub>.

Angewandte Chemie International EditionVol. 64(26)
Hope College (US), University of Pittsburgh (US), Point Park University (US), University of Chicago (US), Rice University (US)
National Science Foundation, U.S. Department of Energy, Welch Foundation, Rice University, University of Pittsburgh, Office of Science, Division of Materials Research, Division of Chemistry, Argonne National Laboratory
Openalex Percentile: Top 8%
Fullerene Chemistry and Applications
3.74
DOIOpen Access PDFOpenAlex
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