Consequences of cooperativity in racemizing supramolecular systems

Seda Cantekin, Huub M.M. Ten Eikelder, Albert J. Markvoort, Martijn A.J. Veld, Peter A. Korevaar, Mark M. Green, Anja R.A. Palmans, E. W. Meijer

Research output: Contribution to journalArticle

Abstract

Saluting the sergeant: Phg-BTA (see scheme) cooperatively self-assembles into helical aggregates and shows unprecedented racemization behavior in the presence of base. In thermodynamically controlled conditions, the addition of a small amount of chiral auxiliary to this mixture results in a deracemization reaction and a final enantiomeric excess of 32 %. A theoretical model is presented to understand in detail the results obtained.

Original languageEnglish (US)
Pages (from-to)6426-6431
Number of pages6
JournalAngewandte Chemie - International Edition
Volume51
Issue number26
DOIs
StatePublished - Jun 25 2012

Keywords

  • deracemization
  • enantiomeric excess
  • nonlinear effects
  • self-assembly
  • supramolecular chemistry

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this

Cantekin, S., Ten Eikelder, H. M. M., Markvoort, A. J., Veld, M. A. J., Korevaar, P. A., Green, M. M., Palmans, A. R. A., & Meijer, E. W. (2012). Consequences of cooperativity in racemizing supramolecular systems. Angewandte Chemie - International Edition, 51(26), 6426-6431. https://doi.org/10.1002/anie.201201701