Anion Rreceptors Based on Intramolecularly Bridged Calix[4]arenes Bearing Ureido Functions.

0470149 - ÚCHP 2017 RIV GB eng J - Journal Article
Řezanková, M. - Budka, J. - Mikšátko, J. - Eigner, V. - Císařová, I. - Cuřínová, Petra - Lhoták, P.
Anion Rreceptors Based on Intramolecularly Bridged Calix[4]arenes Bearing Ureido Functions.
Tetrahedron. Roč. 73, č. 6 (2017), s. 742-749. ISSN 0040-4020. E-ISSN 1464-5416
Institutional support: RVO:67985858
Keywords : calixarene * reductive coupling * anion recognition
OECD category: Organic chemistry
Impact factor: 2.377, year: 2017

A novel type of anion receptor, based on the intramolecularly bridged calix[4]arene immobilized in the cone conformation, is described. The reductive coupling of a distal dialdoxime using Zn/TiCl4 led to calix[4]arene with a meso-1,2-diaminoethane-1,2-diyl bridge that was transformed into the corresponding receptors by reaction with aryl isocyanates. 1H NMR titration experiments revealed that the combination of a unique structural feature (bridge) with arylureido functional groups led to the formation of very potent anion receptors. Contrary to model non-bridged compounds, these well-preorganized receptors can efficiently bind selected anions (H2PO4−, AcO−, BzO−) via hydrogen bonding interactions even in highly competitive solvent (DMSO-d6).
Permanent Link: http://hdl.handle.net/11104/0268248