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Theoretical investigation of the 9,10-bis(1,3-dithiol-2-ylidene)-9,10-dihydroanthracene (exTTF) dimer

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Abstract

9,10-bis(1,3-dithiol-2-ylidene)-9,10-dihydroanthracene (exTTF) is commonly used as pincer in fullerene receptors. In order to understand how this molecule interacts with itself, and thus gain insight in the overall interaction in fullerene receptors which use exTTF as pincer, we studied the exTTF dimer at the M06-2X and ωB97XD levels of theory. The results indicate that this supramolecular complex displays an interaction energy which is larger than the one determined for corannulene. However, the most important difference between both fullerene pincers is not the interaction energy but the number of conformations available, which are larger for the exTTF-based dimer. In effect, at least four completely different structures of the exTTF dimer present interaction energies larger than that computed for corannulene. For this reason, exTTF is expected to: a) adopt strongly dispersion-bound conformations when it is used as pincer to construct fullerene receptors and b) intricate crystallographic structures when stacked with fullerenes.

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Acknowledgments

The authors thank PEDECIBA Quimica for financial support.

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Authors and Affiliations

  1. Computational Nanotechnology, Facultad de Química, DETEMA, UDELAR, CC 1157, 11800, Montevideo, Uruguay

    Pablo A. Denis & Federico Iribarne

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  1. Pablo A. Denis
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  2. Federico Iribarne
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Correspondence to Pablo A. Denis.

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Denis, P.A., Iribarne, F. Theoretical investigation of the 9,10-bis(1,3-dithiol-2-ylidene)-9,10-dihydroanthracene (exTTF) dimer. Struct Chem 26, 171–176 (2015). https://doi.org/10.1007/s11224-014-0480-9

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  • DOI: https://doi.org/10.1007/s11224-014-0480-9

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