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A Computational Investigation of a Molecular Switch

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Department of Chemistry, State University of New York at Buffalo, Buffalo, New York, 14260-3000, United States
Cite this: J. Chem. Educ. 2013, 90, 11, 1528–1532
Publication Date (Web):October 14, 2013
https://doi.org/10.1021/ed400278x
Copyright © 2013 The American Chemical Society and Division of Chemical Education, Inc.

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    Abstract

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    We have developed and implemented a computational experiment that explores the behavior of a [2]catenane as a molecular switch. The experiment introduces mechanically interlocked molecules and discusses their potential as artificial molecular machines. The relaxation rate and lifetime, as well as the ratio of the ground state and the metastable state configurations, are calculated in the gas phase as well as solvents of varying polarity using semiempirical quantum chemical calculations. The π–π donor–acceptor interactions between the two macrocycles comprising the catenane are probed via Hartree–Fock calculations of the frontier molecular orbitals. It is shown that NMR calculations may be employed to aid in the identification of various chemical species. The graphical user interface of the open-source molecular editor Avogadro was employed to visualize the crystal structure of the catenane, followed by quantum chemical calculations using the WebMO graphical interface.

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    Cited By

    This article is cited by 9 publications.

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    2. Gabrielle C. Hoover, Andrew P. Dicks, Dwight S. Seferos. Upper-Year Materials Chemistry Computational Modeling Module for Organic Display Technologies. Journal of Chemical Education 2021, 98 (3) , 805-811. https://doi.org/10.1021/acs.jchemed.0c01325
    3. Daniel P. Miller, Adam Phillips, Herbert Ludowieg, Sarah Swihart, Jochen Autschbach, Eva Zurek. The Computational Design of Two-Dimensional Materials. Journal of Chemical Education 2019, 96 (10) , 2308-2314. https://doi.org/10.1021/acs.jchemed.9b00485
    4. Alexander G. Martynov, John Mack, Aviwe K. May, Tebello Nyokong, Yulia G. Gorbunova, Aslan Yu Tsivadze. Methodological Survey of Simplified TD-DFT Methods for Fast and Accurate Interpretation of UV–Vis–NIR Spectra of Phthalocyanines. ACS Omega 2019, 4 (4) , 7265-7284. https://doi.org/10.1021/acsomega.8b03500
    5. Benjamin P. Pritchard, Scott Simpson, Eva Zurek, and Jochen Autschbach . Computation of Chemical Shifts for Paramagnetic Molecules: A Laboratory Experiment for the Undergraduate Curriculum. Journal of Chemical Education 2014, 91 (7) , 1058-1063. https://doi.org/10.1021/ed400902c
    6. William F. Polik, J. R. Schmidt. WebMO : Web‐based computational chemistry calculations in education and research. WIREs Computational Molecular Science 2022, 12 (1) https://doi.org/10.1002/wcms.1554
    7. Zhongshuai Liang, Hailong Wang, Xin Zheng, Xueye Wang. Theoretical investigation on rotaxanes containing a pyridyl-acyl hydrazone moiety: chemical Z → E and photochemical E → Z isomerizations. Theoretical Chemistry Accounts 2020, 139 (2) https://doi.org/10.1007/s00214-020-2553-8
    8. Gloria Bazargan, Karl Sohlberg. Advances in modelling switchable mechanically interlocked molecular architectures. International Reviews in Physical Chemistry 2018, 37 (1) , 1-82. https://doi.org/10.1080/0144235X.2018.1419042
    9. Nusret Duygu Yilmazer, Martin Korth. Enhanced semiempirical QM methods for biomolecular interactions. Computational and Structural Biotechnology Journal 2015, 13 , 169-175. https://doi.org/10.1016/j.csbj.2015.02.004

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