title: Homothiacalix[4]arenes: synthetic exploration and solid-state structures.
abstract: 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. Moreover, 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.
authors.affiliation: Molecular Design and Synthesis, Department of Chemistry, Katholieke Universiteit Leuven (KUL), Celestijnenlaan 200F, 3001 Leuven, Belgium.
authors.forename: Joice
authors.initials: J
authors.lastname: Thomas
authors.forename: Kristof
authors.initials: K
authors.lastname: Van Hecke
authors.forename: Koen
authors.initials: K
authors.lastname: Robeyns
authors.forename: Wim
authors.initials: W
authors.lastname: Van Rossom
authors.forename: Mahendra P
authors.initials: MP
authors.lastname: Sonawane
authors.forename: Luc
authors.initials: L
authors.lastname: Van Meervelt
authors.forename: Mario
authors.initials: M
authors.lastname: Smet
authors.forename: Wouter
authors.initials: W
authors.lastname: Maes
authors.forename: Wim
authors.initials: W
authors.lastname: Dehaen
mesh_terms: D047250:Calixarenes / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D008024:Ligands; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D012996:Solutions
chemical_list: D008024:Ligands; D012996:Solutions; D047250:Calixarenes