Synthesis of multivalent host and guest molecules for the construction of multithreaded diamide pseudorotaxanes
| Autor: | Christoph A. Schalley, Boris Brusilowskij, Lena Kaufmann, Elisa Franzmann, Wolfgang Maison, Daniel Aicher, Emily Brandt, Arno Wiehe, Nora L. Löw, Egor V. Dzyuba |
|---|---|
| Rok vydání: | 2011 |
| Předmět: |
Chemistry
Stereochemistry Organic Chemistry Convergent synthesis Supramolecular chemistry Sonogashira coupling multivalency Combinatorial chemistry Full Research Paper supramolecular chemistry lcsh:QD241-441 lcsh:Organic chemistry tetralactam macrocycles Quantitative assessment Molecule Moiety lcsh:Q Binding site lcsh:Science Linker pseudorotaxanes |
| Zdroj: | Beilstein Journal of Organic Chemistry Beilstein Journal of Organic Chemistry, Vol 8, Iss 1, Pp 234-245 (2012) |
| ISSN: | 1860-5397 |
| Popis: | A series of di-, tri- and tetravalent axles and wheels for the synthesis of pseudorotaxanes bearing the tetralactam macrocycle/diamide axle binding motif was prepared. Starting from iodinated monovalent precursors, Sonogashira cross-coupling reactions were utilized to couple the binding sites to appropriate spacer groups. Through this “Lego” or “toolbox” approach, the convergent synthesis of host and guests with a well-defined number of the binding sites is possible. In addition, the spatial arrangement of the binding sites can be controlled through the quite rigid connections between linker and binding sites. Although a quantitative assessment of binding strengths was not possible by NMR titration experiments, typical and significant shifts of the signals of the diamide moiety indicate qualitatively the formation of pseudorotaxanes from the axle and wheel precursors. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|