Isolation by crystallization of translational isomers of a bistable donor-acceptor [2]catenane

Cheng Wang, Mark A. Olson, Lei Fang, Diego Benítez, Ekaterina Tkatchouk, Subhadeep Basu, Ashish N. Basuray, Deqing Zhang, Daoben Zhu, William A. Goddard, J. Fraser Stoddart

Research output: Contribution to journalArticlepeer-review

36 Scopus citations

Abstract

The template-directed synthesis of a bistable donor-acceptor [2]catenane wherein both translational isomers - one in which a tetrathiafulvalene unit in a mechanically interlocked crown ether occupies the cavity of a cyclobis(paraquat-p-phenylene) ring and the other in which a 1,5-dioxynaphthalene unit in the crown ether resides inside the cavity of the tetracationic cyclophane - exist in equilibrium in solution, has led to the isolation and separation by hand picking of single crystals colored red and green, respectively. These two crystalline co-conformations have been characterized separately at both the molecular and supramolecular levels, and also by dynamic NMR spectroscopy in solution where there is compelling evidence that the mechanically interlocked molecules are present as a complex mixture of translational, configurational, and conformational isomers wherein the isomerization is best described as being a highly dynamic and adaptable phenomenon.

Original languageEnglish (US)
Pages (from-to)13991-13996
Number of pages6
JournalProceedings of the National Academy of Sciences of the United States of America
Volume107
Issue number32
DOIs
StatePublished - Aug 10 2010

Keywords

  • Mechanical bond formation
  • Stereochemistry
  • Structural isomerism
  • Template-directed synthesis
  • X-ray crystallography

ASJC Scopus subject areas

  • General

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