Supramolecular Ladders from Dimeric Cucurbit[6]uril
2013; Wiley; Volume: 125; Issue: 13 Linguagem: Romeno
10.1002/ange.201300404
ISSN1521-3757
AutoresJames B. Wittenberg, Peter Y. Zavalij, Lyle Isaacs,
Tópico(s)Advanced NMR Techniques and Applications
ResumoAngewandte ChemieVolume 125, Issue 13 p. 3778-3782 Zuschrift Supramolecular Ladders from Dimeric Cucurbit[6]uril† Dr. James B. Wittenberg, Dr. James B. Wittenberg Department of Chemistry and Biochemistry, University of Maryland, College Park, MD 20742 (USA)Search for more papers by this authorDr. Peter Y. Zavalij, Dr. Peter Y. Zavalij Department of Chemistry and Biochemistry, University of Maryland, College Park, MD 20742 (USA)Search for more papers by this authorProf. Dr. Lyle Isaacs, Corresponding Author Prof. Dr. Lyle Isaacs [email protected] Department of Chemistry and Biochemistry, University of Maryland, College Park, MD 20742 (USA)Department of Chemistry and Biochemistry, University of Maryland, College Park, MD 20742 (USA)===Search for more papers by this author Dr. James B. Wittenberg, Dr. James B. Wittenberg Department of Chemistry and Biochemistry, University of Maryland, College Park, MD 20742 (USA)Search for more papers by this authorDr. Peter Y. Zavalij, Dr. Peter Y. Zavalij Department of Chemistry and Biochemistry, University of Maryland, College Park, MD 20742 (USA)Search for more papers by this authorProf. Dr. Lyle Isaacs, Corresponding Author Prof. Dr. Lyle Isaacs [email protected] Department of Chemistry and Biochemistry, University of Maryland, College Park, MD 20742 (USA)Department of Chemistry and Biochemistry, University of Maryland, College Park, MD 20742 (USA)===Search for more papers by this author First published: 18 February 2013 https://doi.org/10.1002/ange.201300404Citations: 9 † We thank the National Science Foundation (CHE-1110911, to L.I.), the Department of Education (P200A090105, GAANN fellowship to J.B.W.), and the University of Maryland (University Fellowship to J.B.W.) for financial support. Read the full textAboutPDF ToolsRequest permissionAdd to favorites ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Graphical Abstract Cucurbit[6]uril-Dimere (verbrückte graue Zylinder; siehe Schema) wurden durch Kondensation von hexamerem Glycoluril mit geeigneten Tetraaldehyden erhalten. Ein Selbstorganisationsprozess dieser Dimere mit Oligoviologenen (blau) führt in Wasser zu supramolekularen Leiterstrukturen, die bezüglich ihrer Abmessungen und ihres Molekülgewichts typischen kleinen Proteinen entsprechen. Supporting Information As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors. Filename Description ange_201300404_sm_miscellaneous_information.pdf2.9 MB miscellaneous_information Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. References 1 1aW. A. Freeman, W. L. Mock, N.-Y. Shih, J. Am. Chem. Soc. 1981, 103, 7367–7368; 10.1021/ja00414a070 CASWeb of Science®Google Scholar 1bJ. Kim, I. S. Jung, S. Y. Kim, E. Lee, J. K. Kang, S. Sakamoto, K. Yamaguchi, K. Kim, J. Am. Chem. 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Growth Des. 2011, 11, 5598–5614. 10.1021/cg201173j CASWeb of Science®Google Scholar 17Competitive binding experiments between 1, 6, and 15 (Supporting Information) establish that 6 and 15 bind with comparable strength to host 1. Accordingly, we expect that the terminal pyridinium-(CH2)6NH3+ and internal pyridinium-(CH2)6-pyridinium binding sites of 17 and 18 will bind with comparable affinity to 1. Google Scholar 18The design of 16–18 feature flexible (CH2)6 spacers connected by rigid viologens; upon complexation with CB[6] dimer 1 we expected that the (CH2)6 spacers would become rigidified, which would favor the formation of supramolecular ladders relative to supramolecular polymers. The insolubility of 1 and the poor solubility of the supramolecular ladders (approximately 10 mM) prevented an examination of the higher concentration regime where supramolecular polymers might be expected to become increasingly favorable. Google Scholar 19Y. Cohen, L. Avram, L. Frish, Angew. Chem. 2005, 117, 524–560; 10.1002/ange.200300637 Google ScholarAngew. Chem. Int. Ed. 2005, 44, 520–544. 10.1002/anie.200300637 CASPubMedWeb of Science®Google Scholar 20If we use the common assumption that these assemblies can be treated as spheres of uniform density, then it is possible to equate the ratio of diffusion coefficients for two assemblies (DA/DB) to the ratio of the cube roots of the molecular weights of the species (MWB)1/3/(MWA)1/3. The Supporting Information contains a full derivation of this equation. Accordingly, for the case of assemblies 1⋅152 (MW=2857) and 12⋅162 (MW=5401) we predict 0.809, which is close to the experimental value of 0.787. Similarly, for the case of assemblies 1⋅152 (MW=2857) and 13⋅172 (MW=7389) we predict 0.729, which is very close to the experimental value of 0.732. For hypothetical assembly 14⋅182 (MW=9933), we would predict 0.660. We can use the experimentally determined diffusion coefficients for 1⋅152 and the 1+18 (4:2) assembly along with the molecular weight of 1⋅152 to estimate the average molecular weight of the mixture of assemblies formed from 1+18 (4:2; MW≈20169). Google Scholar Citing Literature Volume125, Issue13March 25, 2013Pages 3778-3782 This is the German version of Angewandte Chemie. Note for articles published since 1962: Do not cite this version alone. Take me to the International Edition version with citable page numbers, DOI, and citation export. We apologize for the inconvenience. ReferencesRelatedInformation
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