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Interplay between Supramolecularity and Substrate Symmetry in the Dehydrogenation of d-Alaninol on Cu(100) and Cu(110) Surfaces
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    Interplay between Supramolecularity and Substrate Symmetry in the Dehydrogenation of d-Alaninol on Cu(100) and Cu(110) Surfaces
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    Istituto di Struttura della Materia, Consiglio Nazionale delle Ricerche (CNR), Via Fosso del Cavaliere 100, 00133 Roma, Italy
    Centro Interdipartimentale Nanoscienze & Nanotecnologie & Strumentazione (NAST), University of Rome “Tor Vergata”, 00133 Roma, Italy
    § Istituto per lo Studio dei Materiali Nanostrutturati, CNR, Via Salaria Km 29.3, 00015 Monterotondo S. (RM), Italy
    *E-mail: [email protected]. Phone: +39 0649934139.
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    The Journal of Physical Chemistry C

    Cite this: J. Phys. Chem. C 2013, 117, 20, 10545–10551
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    https://doi.org/10.1021/jp401822h
    Published April 18, 2013
    Copyright © 2013 American Chemical Society

    Abstract

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    The adsorption of organic chiral molecules on metallic substrates is widely studied as a tool to obtain chiral surfaces. The chirality transfer from the molecules to the surface is strongly driven by the availability of hydrogen atoms, which guides a specific chiral self-assembled structure. In this paper we report, by combination of photoelectron spectroscopy, low-energy electron diffraction, and density functional theory calculations, on the adsorption of the d-enantiomer of alaninol on Cu(100) and on Cu(110) with the aim of revealing dehydrogenation in the formation of the molecular chiral superstructure. We show that, on both surfaces, at low coverage alaninol is dehydrogenated at the hydroxyl group, whereas at saturated coverage the substrate symmetry, in combination with intermolecular interactions, induces partial amino group dehydrogenation on Cu(100) or inhibits hydroxyl group dehydrogenation on Cu(110).

    Copyright © 2013 American Chemical Society

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    Supporting Information

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    Langmuir isotherm for d-alaninol on Cu(110) at RT and calculated most stable structures for d-alaninol on Cu(110) and Cu(100). This material is available free of charge via the Internet at http://pubs.acs.org.

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    This article is cited by 8 publications.

    1. Zhi-Tao Wang, Yunfei Xu, Mostafa El-Soda, Felicia R. Lucci, Robert J. Madix, Cynthia M. Friend, and E. Charles H. Sykes . Surface Structure Dependence of the Dry Dehydrogenation of Alcohols on Cu(111) and Cu(110). The Journal of Physical Chemistry C 2017, 121 (23) , 12800-12806. https://doi.org/10.1021/acs.jpcc.7b02957
    2. A. Palma and M. Satta . A New Anisotropic Charge-Equilibration Method for Self-Assembly of Organics on Metal Surface: d-Alaninol on Cu(100). Journal of Chemical Theory and Computation 2016, 12 (8) , 4042-4051. https://doi.org/10.1021/acs.jctc.6b00430
    3. Jan Voigt, Mohammed Hasan, Christian Wäckerlin, Anil V. Karnik, Karl‐Heinz Ernst. Switching the on‐surface orientation of oxygen‐functionalized helicene. Chirality 2024, 36 (2) https://doi.org/10.1002/chir.23642
    4. Yalong Xia, Fan Liu, Shuping Cao, Xi Wang, Shijun Xie, Chenmeng Zhang. Interactions of C 5 F 10 O Molecule With Cu (1 1 0) and (1 0 0) Surfaces Based on Density Functional Theory. IEEE Access 2020, 8 , 151012-151018. https://doi.org/10.1109/ACCESS.2020.3017290
    5. Marco Di Giovannantonio, Giorgio Contini. Reversibility and intermediate steps as key tools for the growth of extended ordered polymers via on-surface synthesis. Journal of Physics: Condensed Matter 2018, 30 (9) , 093001. https://doi.org/10.1088/1361-648X/aaa8cb
    6. S Turchini. Conformational effects in photoelectron circular dichroism. Journal of Physics: Condensed Matter 2017, 29 (50) , 503001. https://doi.org/10.1088/1361-648X/aa9730
    7. . Chemisorbed Layers at Interfaces. 2016, 252-302. https://doi.org/10.1039/9781782622161-00252
    8. F. Ronci, R. Gatti, G. Caponi, S. Colonna, G. Galeotti, D. Catone, S. Turchini, T. Prosperi, N. Zema, A. Palma, P. Gori, G. Contini. Organizational chirality expression as a function of the chirality measure of simple amino alcohols on Cu(100). Surface Science 2014, 629 , 41-47. https://doi.org/10.1016/j.susc.2014.02.006

    The Journal of Physical Chemistry C

    Cite this: J. Phys. Chem. C 2013, 117, 20, 10545–10551
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jp401822h
    Published April 18, 2013
    Copyright © 2013 American Chemical Society

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