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Chemical functionalization of boron nitride nanotube via the 1,3-dipolar cycloaddition reaction of azomethine ylide: a quantum chemical study

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Abstract

The first principle exploration at the M05-2X/6-31+G(d,p) level was performed to investigate the chemical functionalizations of (6,0) zigzag single-walled BNNT via the 1,3-dipolar cycloaddition reaction of azomethine ylide. Two types of functionalized BNNTs (D and A complexes) were found in the reaction between 2-methoxy-N,N-dimethylethanamine (MDE) and BNNT. It is energetically favorable for the MDE functional group to interact with the B–N bonds slanted to the tube axis (in D-type complexes). The configuration of the lowest minimum energy corresponds to geometry D1, which the functional group interacts with the end of N-terminated BNNT. The results show that the functionalization of BNNT by MDE functional group is accompanied by a decrease in the band gap, so that this decrease in A complexes is greater than that in the corresponding D ones. Also, the results obtained by natural bond orbital analysis showed that the charge transfer occurs from nanotube to MDE functional group.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, University of Guilan, Rasht, Iran

    Hossein Roohi, Mahjoubeh Jahantab, Shima Rahmdel Delcheh & Bahareh Pakdel Khoshakhlagh

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  1. Hossein Roohi
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  2. Mahjoubeh Jahantab
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  3. Shima Rahmdel Delcheh
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Correspondence to Hossein Roohi.

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Roohi, H., Jahantab, M., Delcheh, S.R. et al. Chemical functionalization of boron nitride nanotube via the 1,3-dipolar cycloaddition reaction of azomethine ylide: a quantum chemical study. Struct Chem 26, 749–759 (2015). https://doi.org/10.1007/s11224-014-0534-z

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