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Host-aided pH-controlled substitution reaction of aryl diazonium salts and sodium azide

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Abstract

Aided by a host molecule, cucurbit[6]uril (CB[6]), pH-controlled substitution reaction between 4-methoxybenzenediazonium tetrafluoroborate and sodium azide was developed. The interaction of CB[6] and aryl diazonium salt was investigated by UV-Vis absorption spectroscopy, mass spectrometry, and 1H NMR titration. The results indicated that under strong acidic conditions (pH < 1) CB[6] and aryl diazonium salt form a 1 : 1 inclusion complex. When the pH value was adjusted to ~3, aryl diazonium salt is gradually released from the supramolecular assemblies and reacted with NaN3. When the pH of the reaction solution was lowered to pH < 1.0, aryl diazonium salt and CB[6] again formed a supra-molecular assemble.

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Authors and Affiliations

  1. Xi’an Modern Chemistry Research Institute, Xi’an, 710065, Shaanxi, People’s Republic of China

    Songsong Guo, Kewei Ding, Wei Liu, Hongli Liu, Min Zhang, Jianglin Hu & Zhongxue Ge

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  1. Songsong Guo
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  2. Kewei Ding
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  3. Wei Liu
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  4. Hongli Liu
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  5. Min Zhang
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  6. Jianglin Hu
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  7. Zhongxue Ge
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Correspondence to Kewei Ding or Zhongxue Ge.

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No human or animal subjects were used in this research.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 8, pp. 1868–1875, August, 2023.

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Guo, S., Ding, K., Liu, W. et al. Host-aided pH-controlled substitution reaction of aryl diazonium salts and sodium azide. Russ Chem Bull 72, 1868–1875 (2023). https://doi.org/10.1007/s11172-023-3971-2

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