A Selective Cage for Azide Ions

  • Author: ChemistryViews.org
  • Published: 26 August 2019
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
  • Source / Publisher: Organic Letters/ACS Publications
  • Associated Societies: American Chemical Society (ACS), USA
thumbnail image: A Selective Cage for Azide Ions

Benzene triimide (BTI) is a planar, electron-deficient, π-conjugated molecule. Due to its three imide groups, it is easy to functionalize and could be a useful building block for larger organic scaffolds.


Qi-Qiang Wang, De-Xian Wang, Beijing National Laboratory for Molecular Sciences, and University of the Chinese Academy of Sciences, Beijing, and colleagues have synthesized a BTI-based cage which can selectively bind anions. The team used three m-xylylene spacers to connect to molecules of BTI. This was achieved by reacting BTI with 1,3-bis(bromomethyl)benzene in the presence of N,N-diisopropylethylamine (DIPEA) as a base.


The resulting cage has an electron-deficient cavity which can bind anions. The team found that it can bind, e.g., N3 (azide, pictured), SCN, and I. Azide is bound particularly strongly and selectively—over 150 and 250 times more strongly than SCN and I, respectively. The team attributes this to the fact that azide is tightly trapped within the cavity and interacts strongly with the π-electron system.


 

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