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Evolution of Br⋯Br contacts in enantioselective molecular recognition during chiral 2D crystallization

Author

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  • Zhen-Yu Yi

    (CAS Key Laboratory of Molecular Nanostructure and Nanotechnology, CAS Research/Education Center for Excellence in Molecular Sciences, Beijing National Laboratory for Molecular Sciences (BNLMS), Institute of Chemistry, Chinese Academy of Sciences
    University of Chinese Academy of Sciences)

  • Xue-Qing Yang

    (CAS Key Laboratory of Molecular Nanostructure and Nanotechnology, CAS Research/Education Center for Excellence in Molecular Sciences, Beijing National Laboratory for Molecular Sciences (BNLMS), Institute of Chemistry, Chinese Academy of Sciences
    Hubei University)

  • Jun-Jie Duan

    (CAS Key Laboratory of Molecular Nanostructure and Nanotechnology, CAS Research/Education Center for Excellence in Molecular Sciences, Beijing National Laboratory for Molecular Sciences (BNLMS), Institute of Chemistry, Chinese Academy of Sciences
    University of Chinese Academy of Sciences)

  • Xiong Zhou

    (Peking University)

  • Ting Chen

    (CAS Key Laboratory of Molecular Nanostructure and Nanotechnology, CAS Research/Education Center for Excellence in Molecular Sciences, Beijing National Laboratory for Molecular Sciences (BNLMS), Institute of Chemistry, Chinese Academy of Sciences)

  • Dong Wang

    (CAS Key Laboratory of Molecular Nanostructure and Nanotechnology, CAS Research/Education Center for Excellence in Molecular Sciences, Beijing National Laboratory for Molecular Sciences (BNLMS), Institute of Chemistry, Chinese Academy of Sciences
    University of Chinese Academy of Sciences)

  • Li-Jun Wan

    (CAS Key Laboratory of Molecular Nanostructure and Nanotechnology, CAS Research/Education Center for Excellence in Molecular Sciences, Beijing National Laboratory for Molecular Sciences (BNLMS), Institute of Chemistry, Chinese Academy of Sciences
    University of Chinese Academy of Sciences)

Abstract

Halogen-mediated interactions play an important role in molecular recognition and crystallization in many chemical and biological systems, whereas their effect on homochiral versus heterochiral recognition and crystallization has rarely been explored. Here we demonstrate the evolution of Br⋯Br contacts in chiral recognition during 2D crystallization. On Ag(100), type I contacts prevail at low coverage and lead to homochiral recognition and the formation of 2D conglomerates; whereas type II contacts mediating heterochiral recognition are suppressed at medium coverage and appear in the racemates induced by structural transitions at high coverage. On Ag(111), type I contacts dominate the 2D crystallization and generate 2D conglomerates exclusively. DFT calculations suggest that the energy difference between type I and type II contacts is reversed upon adsorption due to the substrate induced mismatch energy penalty. This result provides fundamental understanding of halogen-mediated interactions in molecular recognition and crystallization on surface.

Suggested Citation

  • Zhen-Yu Yi & Xue-Qing Yang & Jun-Jie Duan & Xiong Zhou & Ting Chen & Dong Wang & Li-Jun Wan, 2022. "Evolution of Br⋯Br contacts in enantioselective molecular recognition during chiral 2D crystallization," Nature Communications, Nature, vol. 13(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-33446-y
    DOI: 10.1038/s41467-022-33446-y
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    References listed on IDEAS

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    1. Angelika Kühnle & Trolle R. Linderoth & Bjørk Hammer & Flemming Besenbacher, 2002. "Chiral recognition in dimerization of adsorbed cysteine observed by scanning tunnelling microscopy," Nature, Nature, vol. 415(6874), pages 891-893, February.
    2. Jalmar Tschakert & Qigang Zhong & Daniel Martin-Jimenez & Jaime Carracedo-Cosme & Carlos Romero-Muñiz & Pascal Henkel & Tobias Schlöder & Sebastian Ahles & Doreen Mollenhauer & Hermann A. Wegner & Pab, 2020. "Surface-controlled reversal of the selectivity of halogen bonds," Nature Communications, Nature, vol. 11(1), pages 1-8, December.
    3. Ignacio Piquero-Zulaica & Jorge Lobo-Checa & Ali Sadeghi & Zakaria M. Abd El-Fattah & Chikahiko Mitsui & Toshihiro Okamoto & Rémy Pawlak & Tobias Meier & Andrés Arnau & J. Enrique Ortega & Jun Takeya , 2017. "Precise engineering of quantum dot array coupling through their barrier widths," Nature Communications, Nature, vol. 8(1), pages 1-6, December.
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