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Diels–Alder cycloaddition of the silicon–silicon bonds at pentagon junctions of Si-doped non-IPR and SW defective fullerenes

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Abstract

We study the Si doping of contiguous pentagons in the non-IPR C60(D3) and C70(C2v), and SW-defective IPR C60 fullerenes. At that point, Diels–Alder [4 + 2] cycloaddition between butadiene, as diene, and the dangling bonds of silicon dimers of contiguous pentagons in these Si-doped fullerenes, as dienophile, are investigated. The binding energies of 8.05–E8.65 eV/atom are obtained for Si-doping of pentagon–pentagon junctions in C60(D3), C70(C2v), and C60-SW fullerenes, whereupon the quasi-tetrahedral bonding configurations of silicon atoms dependent on sp3 hybridization are formed. Calculated NICS values show Si-doping of pentagon–pentagon junctions prompts strengthened induced diatropic ring currents in heterofullerenes, because of the safeguarding of the conjugated pattern of the hexagonal rings. The results also suggest the higher tendency of charged Si-doped non-IPR fullerenes C54Si66− and C64Si66− to cycloaddition. While the first [4 + 2] cycloaddition leads to an increase in the electrophilicity of the products, electrophilicity decreases with further cycloadditions.

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Acknowledgements

We gratefully acknowledge for the financial support from the Research Council of Alzahra University.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Physics and Chemistry, Alzahra University, 19938-93973, Vanak, Tehran, Iran

    Maryam Anafcheh & Haniyeh Khanmohammadi

  2. Department of Chemistry, Faculty of Sciences, Shahid Beheshti University, 19839-63113, Evin, Tehran, Iran

    Mansour Zahedi

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  1. Maryam Anafcheh
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Correspondence to Maryam Anafcheh.

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Anafcheh, M., Khanmohammadi, H. & Zahedi, M. Diels–Alder cycloaddition of the silicon–silicon bonds at pentagon junctions of Si-doped non-IPR and SW defective fullerenes. Monatsh Chem 152, 241–250 (2021). https://doi.org/10.1007/s00706-021-02743-5

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