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- Title
Insights into the Self‐Filling Effects of Branched Isopropyl Groups on the Conformational and Supramolecular Properties of Isopropoxyprism[6]arene.
- Authors
Del Regno, Rocco; Della Sala, Paolo; Hickey, Neal; Geremia, Silvano; Talotta, Carmen; Neri, Placido; Gaeta, Carmine
- Abstract
In this work, the direct macrocyclization of a prism[6]arene macrocycle bearing branched alkyl chains on the rims is reported. Isopropoxyprism[6]arene adopts in solution and in the solid state a cuboid D2‐conformation in which four isopropyl groups are folded inside the cavity, to give C−H⋅⋅⋅π interactions and filling the internal void. The conformational features of isopropoxyprism[6]arene have been studied by dynamic 1H NMR experiments. The presence of branched isopropyl chains on the prism[6]arene rims, stabilizes the cuboid D2‐conformation to a greater extent than ethyl or propyl groups in PrS[6]Et and PrS[6]nPr. The higher resistance of PrS[6]iPr to open its cuboid D2 conformation, with respect to PrS[6]Et and PrS[6]nPr, also affected its binding abilities. In fact, alkylammonium‐based endo‐cavity complexes of PrS[6]iPr show lower binding constant values than the analogous propoxy/ethoxy‐prism[6]arene complexes.
- Subjects
PROPYL group; ETHYL group; SOLID solutions; BINDING constant; SUPRAMOLECULAR chemistry
- Publication
European Journal of Organic Chemistry, 2023, Vol 26, Issue 39, p1
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.202300608