Self-assembly of 5,11,17,23-Tetranitro-25,26,27,28-tetramethoxythiacalix[4]arene with Neutral Molecules and its Use for Anion Recognition

0420985 - ÚCHP 2014 RIV GB eng J - Journal Article
Macková, M. - Himl, M. - Budka, J. - Pojarová, M. - Císařová, I. - Eigner, V. - Cuřínová, Petra - Dvořáková, H. - Lhoták, P.
Self-assembly of 5,11,17,23-Tetranitro-25,26,27,28-tetramethoxythiacalix[4]arene with Neutral Molecules and its Use for Anion Recognition.
Tetrahedron. Roč. 69, č. 4 (2013), s. 1397-1402. ISSN 0040-4020. E-ISSN 1464-5416
R&D Projects: GA ČR GA203/09/0691; GA AV ČR IAAX08240901
Institutional support: RVO:67985858
Keywords : thiacalixarenes * self assembly * anion recognition
Subject RIV: CC - Organic Chemistry
Impact factor: 2.817, year: 2013

Methylation of 5,11,17,23-tetranitrothiacalix[4]arene with diazomethane leads to the tetramethoxy derivative, which was studied using single-crystal X-ray crystallography. It revealed that this compound, albeit in the 1,3-alternate conformation, can form the inclusion complexes with various solvent molecules possessing acidic methyl groups (ethyl acetate, nitromethane, acetone, acetonitrile) and creates interesting infinite channels filled with solvent molecules. The subsequent transformation of nitro groups into the ureido moieties gave receptors capable of anion recognition even in a highly HB-competitive solvent like DMSO.
Permanent Link: http://hdl.handle.net/11104/0227435