Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 17, Issue 37, Pages 10339-10349Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201101690
Keywords
calixarenes; conformation analysis; macrocyclic ligands; solid-state structures; supramolecular chemistry
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Funding
- FWO (Fund for Scientific Research, Flanders)
- KU Leuven
- Ministerie voor Wetenschapsbeleid
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Homothiacalix[n]arenes have been largely underexposed compared with related (homo)heteracalixarenes, although their inherent structural features are particularly attractive for supramolecular host-guest chemistry. In this contribution, the synthetic macrocyclization protocols that afford homothiacalix[n]arenes have been reinvestigated and optimized, providing straightforward access to the parent homothiacalix[4] arene skeleton. More-over, inner-rim (bis and tetrakis) ester functionalization and dimethylenethia bridge oxidation were successfully performed as well. Solution-phase (variable-temperature) NMR spectroscopy studies and solid-state X-ray structures provided complementary information on the conformational features of the novel macrocycles.
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