Conformational restriction of flexible molecules in solution by a semirigid bis-porphyrin molecular tweezer
2013 (English)In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 69, no 34, 7131-7138 p.Article in journal (Refereed) Published
A semirigid bis-porphyrin molecular clip with a glycoluril backbone has been synthesized. The clip provides an adaptable molecular cavity for binding of diamines. Binding constants for diamines of 104–107 M−1 are orders of magnitude higher than those for monoamines of 103 M−1, indicating a preference to bidentate binding. NMR studies confirmed that binding of bidentate guests occurs inside the clip. Short- and medium-size acyclic molecular guests are locked into a single, extended conformation, and also guests with longer flexible chains exhibit considerably less conformational mobility than when free in solution. The size of the cavity adapts to the guest size, as indicated by modelling studies and self diffusion constants of the complexes.
Place, publisher, year, edition, pages
2013. Vol. 69, no 34, 7131-7138 p.
Conformational analysis, NMR spectroscopy, Hosteguest systems, Supramolecular chemistry, Porphyrinoids
Natural Sciences Organic Chemistry
Research subject Chemistry with specialization in Organic Chemistry
IdentifiersURN: urn:nbn:se:uu:diva-206036DOI: 10.1016/j.tet.2013.06.013ISI: 000322098000027OAI: oai:DiVA.org:uu-206036DiVA: diva2:643288
FunderSwedish Research Council