6533b86dfe1ef96bd12ca98d

RESEARCH PRODUCT

Wide Rim Urethanes Derived from Calix[4]arenes:  Synthesis and Self-Assembly

Yudong CaoVolker BöhmerMyroslav O. Vysotsky

subject

chemistry.chemical_compoundTetraethylammoniumStereochemistryChemistryHydrogen bondDimerOrganic ChemistryPolymer chemistryCalixareneUreaSelf-assemblyChemical synthesisInclusion compound

description

[reaction: see text] Calix[4]arenes 4, substituted at the wide rim by four N-tolyl-urethane groups, were synthesized, as well as derivatives 10a,b bearing two or three tolyl-urea groups beside of one or two urethane group(s). In contrast to tetra-tolyl urea 11, the urethane derivatives do not form hydrogen-bonded, dimeric capsules in CDCl3 or benzene-d6, but the dimerization can be induced for the triurea 10b by tetraethylammonium cations as guests. The quantitative formation of heterodimers is observed for all urethanes 4 and 10a,bin benzene-d6 in mixtures with a "tetra-loop" tetraurea 14, while "bisloop" tetraureas 13 require di- or triurea derivatives 10a,b for a clean heterodimerization.

yearjournalcountryeditionlanguage
2006-04-22The Journal of Organic Chemistry
https://doi.org/10.1021/jo0524369