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Hydrogen Bonding Versus π-Stacking in Charge-Transfer Co-crystals

Cite this: Cryst. Growth Des. 2021, 21, 5, 2609–2613
Publication Date (Web):April 12, 2021
https://doi.org/10.1021/acs.cgd.1c00309
Copyright © 2021 American Chemical Society

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    Abstract

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    We report a comparative study of two structurally similar donor–acceptor complexes with (1a) and without (2a) H-bonding using X-ray crystallography, spectroscopic analysis, and density functional theory calculations. H-Bonding enhances the donor–acceptor interactions, as manifested in a narrower band gap and shorter π-stacking distance in 1a versus 2a, despite 2 being a stronger donor than 1. Thin-film transistors of 1a showed ambipolar charge transport with “double dip” characteristics, whereas no transistor behavior was observed for 2a.

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.cgd.1c00309.

    • Experimental details, cyclic voltammograms, EPR, Kubelka–Munk plots, additional computational details (PDF)

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    CCDC 20635582063559 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, or by emailing [email protected], or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033.

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    Cited By

    This article is cited by 11 publications.

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    2. Jan Alfuth, Katarzyna Kazimierczuk, Tadeusz Połoński, Teresa Olszewska. Intermolecular Hydrogen Bonding Directed by Aryl–Perfluoroaryl π–π Stacking Interactions. Crystal Growth & Design 2023, 23 (9) , 6830-6839. https://doi.org/10.1021/acs.cgd.3c00676
    3. Athira T. John, Akshaya Narayanasamy, Keerthy P. Sudhakaran, Mahesh Hariharan. Resonance-Assisted Hydrogen Bonding and π–π Stacking Modulates the Charge Transfer Coupling in Crystalline Naphthothiazoles. Crystal Growth & Design 2022, 22 (9) , 5686-5693. https://doi.org/10.1021/acs.cgd.2c00798
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    6. R. V. Linko, M. A. Ryabov, V. V. Davydov, V. N. Khrustalev. Charge Transfer Complexes of 9H-Fluoren-9-One Derivatives with 9-Methyl-9H-Carbazole: Quantum Chemical Simulation, Single Crystal X-Ray Diffraction Analysis. Journal of Structural Chemistry 2023, 64 (8) , 1448-1460. https://doi.org/10.1134/S0022476623080097
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    9. Woo Hyuk Jung, Jin Hyuk Park, Seokho Kim, Chunzhi Cui, Dong June Ahn. Molecular doping of nucleic acids into light emitting crystals driven by multisite-intermolecular interaction. Nature Communications 2022, 13 (1) https://doi.org/10.1038/s41467-022-33999-y
    10. Jun Luo, Hongjing Dai, Chenglu Zeng, Dawang Wu, Maoqi Cao. A Theoretical Study of the Halogen Bond between Heteronuclear Halogen and Benzene. Molecules 2022, 27 (22) , 8078. https://doi.org/10.3390/molecules27228078
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