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Mechanochemistry of Cubane

Cite this: J. Am. Chem. Soc. 2022, 144, 50, 22865–22869
Publication Date (Web):December 8, 2022
https://doi.org/10.1021/jacs.2c10878
Copyright © 2022 American Chemical Society

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    Abstract

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    We report the mechanochemical reactivity of the highly strained pentacyclic hydrocarbon cubane. The mechanical reactivity of cubane is explored for three regioisomers with 1,2-, 1,3-, and 1,4-substituted pulling attachments. Whereas all compounds can be activated thermally, mechanical activation is observed via pulsed ultrasonication of cubane-containing polymers only when force is applied via 1,2-attachment. The single observed product of the force-coupled reaction is a thermally inaccessible syn-tricyclooctadiene, in contrast to cyclooctatetraene (observed thermally) or a pair of cyclobutadienes that would result from sequential cyclobutane scission. We further quantify the mechanochemical reactivity of cubane by single molecule force spectroscopy, and force-coupled rate constants for ring opening reach ∼33 s–1 at a force of ∼1.55 nN, lower than forces of 1.8–2.0 nN that are typical of conventional cyclobutanes.

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/jacs.2c10878.

    • General experimental details; synthetic details; sonication experiments; thermolysis experiments; single molecule force spectroscopy (SMFS) experiments; computational analyses (output files available at DOI: https://doi.org/10.7924/r47h1r86c); NMR spectra (PDF)

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    Cited By

    This article is cited by 4 publications.

    1. Shihao Ding, Wenkai Wang, Anne Germann, Yiting Wei, Tianyi Du, Jan Meisner, Rong Zhu, Yun Liu. Bicyclo[2.2.0]hexene: A Multicyclic Mechanophore with Reactivity Diversified by External Forces. Journal of the American Chemical Society 2024, 146 (9) , 6104-6113. https://doi.org/10.1021/jacs.3c13589
    2. Matías Horst, Jan Meisner, Jinghui Yang, Tatiana B. Kouznetsova, Stephen L. Craig, Todd J. Martínez, Yan Xia. Mechanochemistry of Pterodactylane. Journal of the American Chemical Society 2024, 146 (1) , 884-891. https://doi.org/10.1021/jacs.3c11293
    3. Xiaojun He, Yancong Tian, Robert T. O’Neill, Yuanze Xu, Yangju Lin, Wengui Weng, Roman Boulatov. Coumarin Dimer Is an Effective Photomechanochemical AND Gate for Small-Molecule Release. Journal of the American Chemical Society 2023, 145 (42) , 23214-23226. https://doi.org/10.1021/jacs.3c07883
    4. Kelsie E. Wentz, Yunxin Yao, Ilia Kevlishvili, Tatiana B. Kouznetsova, Braden A. Mediavilla, Heather J. Kulik, Stephen L. Craig, Rebekka S. Klausen. Systematic Investigation of Silicon Substitution on Single Macromolecule Mechanics. Macromolecules 2023, 56 (17) , 6776-6782. https://doi.org/10.1021/acs.macromol.3c01066

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