TY - JOUR A1 - Löw, Nora L. A1 - Dzyuba, Egor V. A1 - Brusilowskij, Boris A1 - Kaufmann, Lena A1 - Franzmann, Elisa A1 - Maison, Wolfgang A1 - Brandt, Emily A1 - Aicher, Daniel A1 - Wiehe, Arno A1 - Schalley, Christoph A. T1 - Synthesis of multivalent host and guest molecules for the construction of multithreaded diamide pseudorotaxanes JF - Beilstein Journal of Organic Chemistry PY - 2012/// VL - 8 SP - 234 EP - 245 SN - 1860-5397 DO - 10.3762/bjoc.8.24 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.8.24 KW - multivalency KW - pseudorotaxanes KW - Sonogashira coupling KW - supramolecular chemistry KW - tetralactam macrocycles N2 - 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. ER -