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Traulsen NL, Traulsen CH, Deutinger PM, et al. Chelate cooperativity effects on the formation of di- and trivalent pseudo[2]rotaxanes with diketopiperazine threads and tetralactam wheels. Org Biomol Chem. 2015;13(44):10881-7doi: 10.1039/c5ob01687h.
Traulsen, N. L., Traulsen, C. H., Deutinger, P. M., Müller, S., Schmidt, D., Linder, I., & Schalley, C. A. (2015). Chelate cooperativity effects on the formation of di- and trivalent pseudo[2]rotaxanes with diketopiperazine threads and tetralactam wheels. Organic & biomolecular chemistry, 13(44), 10881-7. https://doi.org/10.1039/c5ob01687h
Traulsen, Nora L, et al. "Chelate cooperativity effects on the formation of di- and trivalent pseudo[2]rotaxanes with diketopiperazine threads and tetralactam wheels." Organic & biomolecular chemistry vol. 13,44 (2015): 10881-7. doi: https://doi.org/10.1039/c5ob01687h
Traulsen NL, Traulsen CH, Deutinger PM, Müller S, Schmidt D, Linder I, Schalley CA. Chelate cooperativity effects on the formation of di- and trivalent pseudo[2]rotaxanes with diketopiperazine threads and tetralactam wheels. Org Biomol Chem. 2015 Nov 28;13(44):10881-7. doi: 10.1039/c5ob01687h. Epub 2015 Sep 14. PMID: 26366717.
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Org Biomol Chem. 2015 Nov 28;13(44):10881-7. doi: 10.1039/c5ob01687h. Epub 2015 Sep 14.

Chelate cooperativity effects on the formation of di- and trivalent pseudo[2]rotaxanes with diketopiperazine threads and tetralactam wheels.

Organic & biomolecular chemistry

Nora L Traulsen, Christoph H-H Traulsen, Peter M Deutinger, Sebastian Müller, Deborah Schmidt, Igor Linder, Christoph A Schalley

Affiliations

  1. Institut für Chemie und Biochemie der Freien Universität Berlin, Takustr. 3, 14195 Berlin, Germany. [email protected].

PMID: 26366717 DOI: 10.1039/c5ob01687h

Abstract

The formation of singly, doubly and triply threaded pseudo[2]rotaxanes with diketopiperazine threads and tetralactam wheels is investigated with respect to chelate cooperativity effects on multivalent binding. Two series of guest molecules are prepared which differ with respect to their spacers, one with preorganised centrepieces with di- or tripodal roof-like structures, one with more flexible spacers. The thermodynamics of pseudorotaxane formation is examined using isothermal titration calorimetry and (1)H NMR spectroscopy. Force-field calculations provide more detailed structural insight and help rationalizing the thermodynamic data. All di- and trivalent pseudorotaxanes exhibit positive chelate cooperativity presumably arising from spacer-spacer interactions. Higher cooperativity factors are observed for the more preorganised threads.

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