Triggering activity of catalytic rod-like supramolecular polymers

Elisa Huerta, Bas Van Genabeek, Brigitte A.G. Lamers, Marcel M.E. Koenigs, E. W. Meijer, Anja R.A. Palmans

Research output: Contribution to journalArticleAcademicpeer-review

32 Citations (Scopus)
6 Downloads (Pure)

Abstract

Supramolecular polymers based on benzene-1,3,5- tricarboxamides (BTAs) functionalized with an L- or D-proline moiety display high catalytic activity towards aldol reactions in water. High turnover frequencies (TOF) of up to 27 × 10-4 s-1 and excellent stereoselectivities (up to 96% de, up to 99% ee) were observed. In addition, the catalyst could be reused and remained active at catalyst loadings and substrate concentrations as low as 0.1 mol% and 50 mm, respectively. A temperature-induced conformational change in the supramolecular polymer triggers the high activity of the catalyst. The supramolecular polymer's helical sense in combination with the configuration of the proline (L- or D) is responsible for the observed selectivity.

Original languageEnglish
Pages (from-to)3682-3690
Number of pages9
JournalChemistry : A European Journal
Volume21
Issue number9
DOIs
Publication statusPublished - 22 Jan 2015

Keywords

  • Aldol reaction
  • Organocatalysis
  • Proline
  • Self-assembly
  • Supramolecular polymers

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