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

Wang, Cheng and Olson, Mark A. and Fang, Lei and Benítez, Diego and Tkatchouk, Ekaterina and Basu, Subhadeep and Basuray, Ashish N. and Zhang, Deqing and Zhu, Daoben and Goddard, William A., III and Stoddart, J. Fraser (2010) Isolation by crystallization of translational isomers of a bistable donor-acceptor [2]catenane. Proceedings of the National Academy of Sciences of the United States of America, 107 (32). pp. 13991-13996. ISSN 0027-8424. PMCID PMC2922539. https://resolver.caltech.edu/CaltechAUTHORS:20100915-093919638

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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.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1073/pnas.1009302107DOIArticle
http://www.pnas.org/cgi/doi/10.1073/pnas.1009302107PublisherArticle
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2922539/PubMed CentralArticle
ORCID:
AuthorORCID
Wang, Cheng0000-0002-1939-1422
Goddard, William A., III0000-0003-0097-5716
Stoddart, J. Fraser0000-0003-3161-3697
Additional Information:© 2010 National Academy of Sciences. Communicated by M. Frederick Hawthorne, University of Missouri, Columbia, MO, June 29, 2010 (received for review April 21, 2010). This material is based upon work supported by the National Science Foundation under CHE-0924620. The authors also wish to thank and acknowledge the support from the Air Force Office of Scientific Research under the Multidisciplinary Research Program of the University Research Initiative (MURI), Award FA9550-07-1-0534 entitled “Bioinspired Supramolecular Enzymatic Systems.” Author contributions: C.W., M.A.O., L.F., and J.F.S. designed research; C.W., M.A.O., L.F., S.B., and A.N.B. performed research; D.B., E.T., D. Zhang, D. Zhu, and W.A.G. contributed new reagents/analytic tools; C.W., M.A.O., L.F., and J.F.S. analyzed data; and C.W., M.A.O., L.F. and J.F.S. wrote the paper. The authors declare no conflict of interest. Data deposition: Crystallographic data (excluding structure factors) for the structures have been deposited in the Cambridge Structural Database, Cambridge Crystallographic Data Centre, www.ccdc.cam.ac.uk/, Cambridge CB2 1EZ, United Kingdom (CSD reference nos. 782651 and 782652). C.W. and M.A.O. contributed equally to this work. This article contains supporting information online at www.pnas.org/lookup/suppl/doi:10.1073/pnas.1009302107/-/DCSupplemental.
Funders:
Funding AgencyGrant Number
NSFCHE-0924620
Air Force Office of Scientific Research (AFOSR)FA9550-07-1-0534
Subject Keywords:mechanical bond formation; stereochemistry; template-directed synthesis; structural isomerism; X-ray crystallography
Issue or Number:32
PubMed Central ID:PMC2922539
Record Number:CaltechAUTHORS:20100915-093919638
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20100915-093919638
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:19966
Collection:CaltechAUTHORS
Deposited By: Jason Perez
Deposited On:15 Sep 2010 18:33
Last Modified:09 Mar 2020 13:19

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