Inverse Electron Demand Diels–Alder Reaction on M <sub>3</sub> N@C <sub>80</sub> (M=Lu, Sc): Reactivity and Reversibility Enable Chemical Separation of Metallofullerenes

Endohedral metallofullerenes are chemically more inert compared to empty fullerenes, primarily due to their intramolecular electron transfer. In this work, we report an inverse electron demand Diels-Alder (IEDDA) reaction on M<sub>3</sub>N@C<sub>80</sub> (M=Lu, Sc), where they show significantly higher reactivity than empty fullerenes. The molecular structures of the [4+2] cycloadducts were unambiguously characterized. Moreover, the cycloadducts can fully revert to pristine M<sub>3</sub>N@C<sub>80</sub> via retro-cycloaddition upon thermal treatment. With the unusual reactivity and reversibility, the IEDDA reaction enables an effective separation approach for metallofullerenes from their soot extracts, opening path to efficient and economical scale-up synthesis of metallofullerenes in laboratory and industrial settings.

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Publication Details

Journal
Angewandte Chemie International Edition
Published
2025-02-11
DOI
https://doi.org/10.1002/anie.202424776
Citations
1
Primary Topic
Fullerene Chemistry and Applications
Type
article
Field-Weighted Citation Impact
0.94

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article

Inverse Electron Demand Diels–Alder Reaction on M 3 N@C 80 (M=Lu, Sc): Reactivity and Reversibility Enable Chemical Separation of Metallofullerenes

Josep M. Poblet, Yanbang Li, Jianyuan Zhang, Ian Ferraro et al.
1 citations
Angewandte Chemie International Edition
Fullerene Chemistry and Applications
0.94
article

Inverse Electron Demand Diels–Alder Reaction on M 3 N@C 80 (M=Lu, Sc): Reactivity and Reversibility Enable Chemical Separation of Metallofullerenes

Josep M. Poblet, Yanbang Li, Jianyuan Zhang, Ian Ferraro, Antonio Rodríguez‐Fortea, Laura Abella, Thomas J. Emge, Anyin Li, Steven Stevenson, Yue Sun, Sheng Zhu
article en
1 citations

Abstract

Endohedral metallofullerenes are chemically more inert compared to empty fullerenes, primarily due to their intramolecular electron transfer. In this work, we report an inverse electron demand Diels-Alder (IEDDA) reaction on M<sub>3</sub>N@C<sub>80</sub> (M=Lu, Sc), where they show significantly higher reactivity than empty fullerenes. The molecular structures of the [4+2] cycloadducts were unambiguously characterized. Moreover, the cycloadducts can fully revert to pristine M<sub>3</sub>N@C<sub>80</sub> via retro-cycloaddition upon thermal treatment. With the unusual reactivity and reversibility, the IEDDA reaction enables an effective separation approach for metallofullerenes from their soot extracts, opening path to efficient and economical scale-up synthesis of metallofullerenes in laboratory and industrial settings.

Angewandte Chemie International EditionVol. 64(16)
Rutgers, The State University of New Jersey (US), University of New Hampshire (US), Indiana University – Purdue University Fort Wayne (US), University of New Hampshire at Manchester (US), Purdue University Fort Wayne (US), Universitat Rovira i Virgili (ES)
National Science Foundation, Generalitat de Catalunya, Division of Chemistry
Openalex Percentile: Top 29%
Fullerene Chemistry and Applications
0.94
DOIOpen Access PDFOpenAlex
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