Synthesis of New Calix[4]arene-Based Ionophores

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Title:Synthesis of New Calix[4]arene-Based Ionophores
Creators:
Arduini, Arturo
Bozzoli, Marcella
Massera, Chiara
Pochini, Andrea
Secchi, Andrea
Ugozzoli, Franco
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 69, 6, pp. 1309-1324
Uncontrolled Keywords:Calixarenes, Ionophores, X-Ray diffraction, Strontium, Supramolecular chemistry, Alkali metals, Complexation

Abstract

A synthesis of new calix[4]arene-based ionophores is reported. These ligands are characterized by the presence of two types of coordination sites on their lower rim: one crowning unit of different length, linking two proximal calix[4]arene phenolic oxygens, and two esters or amide groups acting as additional hard binding sites. The choice of the proper reaction conditions, such as the base counterion and the solvent polarity, during the functionalization of the macrocycle lower rim, allows to modulate the stereochemistry of the final ligands. In this way the ligands in <i>cone</i> and <i>1,2-alternate</i> conformations were obtained in good yields. Complexation properties of these new compounds towards alkali and alkaline-earth cations were studied by means of liquid-liquid extraction experiments. The X-ray solid state structure of the <i>p</i>-<i>tert</i>-butylcalix[4]arene-<i>N</i>,<i>N</i>-diethylacetamide-crown-5 (<strong>6a</strong>) complex with strontium picrate shows the effective cooperativity among the two type of coordination site in the binding event. <p>

Title:Synthesis of New Calix[4]arene-Based Ionophores
Creators:
Arduini, Arturo
Bozzoli, Marcella
Massera, Chiara
Pochini, Andrea
Secchi, Andrea
Ugozzoli, Franco
Uncontrolled Keywords:Calixarenes, Ionophores, X-Ray diffraction, Strontium, Supramolecular chemistry, Alkali metals, Complexation
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:69
Number:6
Page Range:pp. 1309-1324
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20041309UNSPECIFIED
ID Code:2276
Item Type:Article
Deposited On:06 Feb 2009 17:17
Last Modified:06 Feb 2009 16:17

Citation

Arduini, Arturo; Bozzoli, Marcella; Massera, Chiara; Pochini, Andrea; Secchi, Andrea; Ugozzoli, Franco (2004) Synthesis of New Calix[4]arene-Based Ionophores. Collection of Czechoslovak Chemical Communications, 69 (6). pp. 1309-1324. ISSN 0010-0765

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