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Crystal Structure of Anion-Radical Salts of 7,7,8,8-tetracyanoquinodimethane with N-xylyl-pyridinium and N-xylyl-isoquinolinium Cations

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Abstract

Novel anion-radical salts of 7,7,8,8-tetracyanoquinodimethane (TCNQ) with N-xylyl-pyridinium and N-xylyl-isoquinolinium cations of complex composition ((N-Xy-Py)(TCNQ)2(CH3CN) (1) and (N-Xy-iQn)(TCNQ)2 (2), respectively) have been synthesized. The crystal and molecular structures of 1 and 2 are determined using X-ray diffraction (XRD) analysis. Salts are crystallized into different systems: the (N-Xy-Py)(TCNQ)2(CH3CN) structure belongs to the orthorhombic system, while the (N-Xy-iQn)(TCNQ)2 structure belongs to the triclinic system. Crystals of salt 1 contain dimerized stacks of anion-radicals of the ABAB type, while the stacks in structure 2 are tetramerized. This structural distortion does not facilitate high electrical conductivity, which is confirmed by the IR spectral data: the spectra of salts 1 and 2 do not exhibit any specific features of high-conductivity TCNQ salts (continuous absorption and anomalous line broadening). This fact can be caused by the Peierls instability, which induces dimerization of stacks in crystals of salt 1 and tetramerization of stacks in crystals of salt 2.

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Funding

PhD V.O. Yaroshenko acknowledges the support of the National Science Center within the SONATA 10 program (grant no. 2015/19/D/ST5/02774).

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Authors and Affiliations

  1. Institute of Chemistry, Jan Kochanowski University, 25-406, Kielce, Poland

    T. N. Starodub & D. Stepen’

  2. Institute of Inorganic Chemistry, Karlsruhe Institute of Technology, 76131, Karlsruhe, Germany

    D. Fenske & O. Fuhr

  3. Institute of Nanotechnology (INT) and Karlsruhe Nano Micro Facility (KNMF), Karlsruhe Institute of Technology (KIT), 76344, Eggenstein-Leopoldshafen, Germany

    D. Fenske & O. Fuhr

  4. Lehn-Institute for Functional Materials, School of Chemistry and Chemical Engineering, Sun Yat-Sen University, 510275, Guangzhou, China

    D. Fenske

  5. University of Helsinki, 00014, Helsinki, Finland

    V. O. Yaroshenko

  6. Matej Bel University, 974 01, Banská Bystrica, Slovakia

    V. O. Yaroshenko

Authors
  1. T. N. Starodub
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  2. D. Fenske
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  3. O. Fuhr
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  4. V. O. Yaroshenko
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  5. D. Stepen’
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Correspondence to T. N. Starodub.

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Translated by Yu. Sin’kov

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Starodub, T.N., Fenske, D., Fuhr, O. et al. Crystal Structure of Anion-Radical Salts of 7,7,8,8-tetracyanoquinodimethane with N-xylyl-pyridinium and N-xylyl-isoquinolinium Cations. Crystallogr. Rep. 67, 356–363 (2022). https://doi.org/10.1134/S1063774522030191

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  • DOI: https://doi.org/10.1134/S1063774522030191

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