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Experimental and theoretical study on cation–π interaction of Ag+ with [6]helicene

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Abstract

By employing electrospray ionization mass spectrometry, it was proven experimentally that the [6]helicene–Ag+ complex (i.e., [Ag(C26H16)]+) exists in the gas phase. Further, applying quantum mechanical DFT calculations, the most probable structure of this cationic complex [Ag(C26H16)]+ was derived. Finally, in the solid state, the complex [6]helicene–silver triflate–monohydrate (i.e., C26H16–AgCF3SO3–H2O), crystallizing in the monoclinic system with the centro-symmetric P21/c space group, was prepared and analyzed. The characteristic feature of this complex packing in the solid state is the formation of the separated [6]helicene and silver triflate domains. In both of these binding modes, the investigated [6]helicene ligand functions as a molecular tweezer for the univalent silver cation.

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Acknowledgments

This work was supported by the Grant Agency of Faculty of Environmental Sciences, Czech University of Life Sciences, Prague, Project No.: 42900/1312/3114 “Environmental Aspects of Sustainable Development of Society,” by the Czech Ministry of Education, Youth, and Sports (projects MSM 6046137307 and MSM 0021620857), as well as by the Grant Agency of the Czech Republic (Projects 13-21409P and P207/10/1124). Further, we appreciate for the financial support from the Technology Agency of the Czech Republic (Grant No.: TA01010646) and the Czech Ministry of Industry and Trade (Grant No.: FR-T13/628). Finally, the authors of this study thank Prof. Stanislav Böhm from Prague for some theoretical calculations.

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Authors and Affiliations

  1. Faculty of Environmental Sciences, Czech University of Life Sciences, Prague, Kamýcká 129, 165 21, Prague 6, Czech Republic

    Emanuel Makrlík

  2. Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo Sq. 2, 166 10, Prague 6, Czech Republic

    Jana Jaklová Dytrtová

  3. Department of Analytical Chemistry, University of Chemistry and Technology, Prague, Technická 5, 166 28, Prague 6, Czech Republic

    Petr Vaňura

  4. Department of Inorganic Chemistry, Faculty of Sciences, Charles University, Hlavova 2030, 128 43, Prague 2, Czech Republic

    Ivana Císařová

  5. Institute of Chemical Process Fundamentals, Academy of Sciences of the Czech Republic, Rozvojová 2/135, 165 02, Prague 6, Czech Republic

    Jan Sýkora, Vladimír Církva & Jan Storch

  6. J. Heyrovský Institute of Physical Chemistry, Academy of Sciences of the Czech Republic, Dolejškova 2155/3, 182 23, Prague 8, Czech Republic

    Miroslav Polášek

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  1. Emanuel Makrlík
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Correspondence to Emanuel Makrlík.

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Makrlík, E., Jaklová Dytrtová, J., Vaňura, P. et al. Experimental and theoretical study on cation–π interaction of Ag+ with [6]helicene. Struct Chem 27, 627–635 (2016). https://doi.org/10.1007/s11224-015-0595-7

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