Synthesis of multivalent host and guest molecules for the construction of multithreaded diamide pseudorotaxanes

Beilstein Journal of Organic Chemistry

Daniel Aicher¹  Emily Brandt¹  Lena Kaufmann²  Egor V. Dzyuba²  Christoph A. Schalley²  Boris Brusilowskij²  Arno Wiehe²  Nora L. Löw²  Wolfgang Maison³  Elisa Franzmann³ 

[1] Biolitec research GmbH, Otto-Schott-Str. 15, 07745 Jena, Germany;Institut für Chemie und Biochemie der Freien Universität Berlin, Takustr. 3, 14195 Berlin, Germany;Pharmazeutische und Medizinische Chemie, Universität Hamburg, Bundesstr. 45, 20146 Hamburg, Germany;

关键词: multivalency;    pseudorotaxanes;    Sonogashira coupling;    supramolecular chemistry;    tetralactam macrocycles;   

DOI  :  10.3762/bjoc.8.24

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown