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A mechanistic study of Lewis acid-catalyzed covalent organic framework formation

Chemical Science, ISSN: 2041-6520, Vol: 2, Issue: 8, Page: 1588-1593
2011
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Metrics Details

  • Citations
    131
    • Citation Indexes
      131
  • Captures
    151

Article Description

Three boronate ester-linked covalent organic frameworks (COFs) were synthesized using a new approach that employs polyfunctional boronic acid and acetonide-protected catechol reactants in the presence of the Lewis acid catalyst BF·OEt. This transformation avoids the use of unstable and insoluble polyfunctional catechols. The COF-5 and COF-10 hexagonal lattices were obtained from a triphenylene tris(acetonide) and the appropriate diboronic acid linker, whereas a square Ni phthalocyanine COF was prepared from the appropriate Ni phthalocyanine tetra(acetonide). The powder X-ray diffraction, infrared spectra, and measured surface areas of these materials matched or exceeded previously reported values. A mechanistic study of this transformation revealed that the dehydrative trimerization of boronic acids to boroxines and the formation of a nonproductive aryl boronic acid-BF complex strongly affect the rate of boronate ester formation. Crossover experiments employing substituted boronate ester derivatives suggest that ester hydrolysis is the most likely exchange mechanism during COF formation under BF·OEt-catalyzed conditions. © The Royal Society of Chemistry 2011.

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