Journal ArticleDOI
Synthesis and Metal Ion Complexation Studies of Proton-Ionizable Calix[4]azacrown Ethers in the 1,3-Alternate Conformation
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TLDR
These compounds show high potassium selectivity over other metal ions as shown by two-phase extraction, bulk liquid membrane, and 1H NMR studies on a ligand-metal complex.Abstract:
A series of novel N-chromogenic calix[4]arene azacrown ethers were synthesized as selective extractants of potassium ion. 1,3-Alternate calix[4]arene azacrown ethers were prepared by reacting 25,27-dipropyloxy-26,28-bis(5-chloro-3-oxapentyloxy) calix[4]arenes with p-toluenesulfonamide in the presence of potassium carbonate. The coupling reaction of calix[4]arene azacrown ether with 2-hydroxy-5-nitrobenzyl bromide in the presence of triethylamine in THF gave the chromogenic calix[4]arene azacrown ether in moderate yield. These compounds show high potassium selectivity over other metal ions as shown by two-phase extraction, bulk liquid membrane, and 1H NMR studies on a ligand−metal complex. It is assumed that the OH of the chromogenic group attached on nitrogen can assist the complexation by encapsulation of the metal.read more
Citations
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Crown ethers: sensors for ions and molecular scaffolds for materials and biological models.
Journal ArticleDOI
An Excimer-Based, Binuclear, On−Off Switchable Calix[4]crown Chemosensor
TL;DR: Computational results show that the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbitals (LUMO) of the two pyrene moieties interact under UV irradiation of 1 and its K+ complex, while such HOMO-LumO interactions are absent in the Pb2+ complex.
Journal ArticleDOI
Calixarene-Based Molecules for Cation Recognition
TL;DR: In this article, a review discusses molecular design principles of calixarene-type macrocycles for ion recognition and gives examples on the relationship between structure and selectivity, however without attempting to cover all the different approaches.
Journal ArticleDOI
Crown-6-calix[4]arene-Capped Calix[4]pyrrole: An Ion-Pair Receptor for Solvent-Separated CsF Ions
Jonathan L. Sessler,Sung Kuk Kim,Dustin E. Gross,Chang-Hee Lee,Jong Seung Kim,Vincent M. Lynch +5 more
TL;DR: An ion-pair receptor, 1, containing both cation- and anion-recognizing sites, has been synthesized and characterized and confirmed that 1 forms stable 1:1 complexes with CsF in solution and in the solid state in spite of the large separation enforced between the receptor-bound anion and cation.
Journal ArticleDOI
A calix[4]arene strapped calix[4]pyrrole: an ion-pair receptor displaying three different cesium cation recognition modes
Sung Kuk Kim,Jonathan L. Sessler,Dustin E. Gross,Chang-Hee Lee,Jong Seung Kim,Vincent M. Lynch,Lætitia H. Delmau,Benjamin Hay +7 more
TL;DR: An ion-pair receptor, the calix[ 4]pyrrole-calix[4]arene pseudodimer 2, bearing a strong anion- Recognition site but not a weak cation-recognition site, has been synthesized and characterized by standard spectroscopic means and via single-crystal X-ray diffraction analysis.
References
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Journal ArticleDOI
Synthesis, Complexation, and Membrane Transport Studies of 1,3-Alternate Calix[4]arene-crown-6 Conformers: A New Class of Cesium Selective Ionophores
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Chromo- and fluoroionophores. A new class of dye reagents
Hans Gerd Loehr,Fritz Voegtle +1 more
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Metal complexes of cyclic tetra-azatetra-acetic acids.
TL;DR: The cyclic tetra-aza complexones cDOTA, cTRITA and cTETA have been synthesized and characterized by elemental analysis, titration, melting-point determination and NMR (and infrared) spectroscopy and neither this ligand nor the other two offer advantages over EDTA or DCTA for the complexometric titration of transition metals.
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