title: Synthesis of multivalent host and guest molecules for the construction of multithreaded diamide pseudorotaxanes.
abstract: 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.
authors.affiliation: Institut für Chemie und Biochemie der Freien Universität Berlin, Takustr. 3, 14195 Berlin, Germany.
authors.forename: Nora L
authors.initials: NL
authors.lastname: Löw
authors.affiliation: Institut für Chemie und Biochemie der Freien Universität Berlin, Takustr. 3, 14195 Berlin, Germany.
authors.forename: Egor V
authors.initials: EV
authors.lastname: Dzyuba
authors.affiliation: Institut für Chemie und Biochemie der Freien Universität Berlin, Takustr. 3, 14195 Berlin, Germany.
authors.forename: Boris
authors.initials: B
authors.lastname: Brusilowskij
authors.affiliation: Institut für Chemie und Biochemie der Freien Universität Berlin, Takustr. 3, 14195 Berlin, Germany.
authors.forename: Lena
authors.initials: L
authors.lastname: Kaufmann
authors.affiliation: Pharmazeutische und Medizinische Chemie, Universität Hamburg, Bundesstr. 45, 20146 Hamburg, Germany.
authors.forename: Elisa
authors.initials: E
authors.lastname: Franzmann
authors.affiliation: Pharmazeutische und Medizinische Chemie, Universität Hamburg, Bundesstr. 45, 20146 Hamburg, Germany.
authors.forename: Wolfgang
authors.initials: W
authors.lastname: Maison
authors.affiliation: Biolitec research GmbH, Otto-Schott-Str. 15, 07745 Jena, Germany.|Charité - Universitätsmedizin, International Graduate Program Medical Neurosciences, Charitéplatz 1, 10117 Berlin, Germany.
authors.forename: Emily
authors.initials: E
authors.lastname: Brandt
authors.affiliation: Biolitec research GmbH, Otto-Schott-Str. 15, 07745 Jena, Germany.|WITEGA Laboratorien Berlin-Adlershof GmbH, Magnusstr. 11, 12489 Berlin, Germany.
authors.forename: Daniel
authors.initials: D
authors.lastname: Aicher
authors.affiliation: Institut für Chemie und Biochemie der Freien Universität Berlin, Takustr. 3, 14195 Berlin, Germany.|Biolitec research GmbH, Otto-Schott-Str. 15, 07745 Jena, Germany.
authors.forename: Arno
authors.initials: A
authors.lastname: Wiehe
authors.affiliation: Institut für Chemie und Biochemie der Freien Universität Berlin, Takustr. 3, 14195 Berlin, Germany.
authors.forename: Christoph A
authors.initials: CA
authors.lastname: Schalley