Photocontrol of Complexation of Neutral and Cationic Species by <i>p‐tert‐</i>Butylcalix[4]arene Tetraethyl Ester

Creaven, Bernadette S.; Deasy, Mary; McKenna, Catherine; Murray, Brian A.; Tobin, Darren

doi:10.1002/ejic.200400705

Cited by 3 publications

(1 citation statement)

References 26 publications

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“…Creaven et al noted a similar phenomenon in their studies on a number of sodium salt complexes of the tetraethyl ester p-tert-butylcalix [4]arene (57) which were isolated both with and without upper-rim encapsulated acetonitrile or methanol [71] ( Fig. 29).…”

Section: Complexationmentioning

confidence: 68%

Coordination chemistry of calix[4]arene derivatives with lower rim functionalisation and their applications

Creaven

Donlon

McGinley

2009

Coordination Chemistry Reviews

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Section: Complexationmentioning

confidence: 68%

Coordination chemistry of calix[4]arene derivatives with lower rim functionalisation and their applications

Creaven

Donlon

McGinley

2009

Coordination Chemistry Reviews

Self Cite

206

150

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Unusual reactivity of copper(I) complexes of functionalised calix[4]arenes

Creaven¹,

Gernon²,

McCormac³

et al. 2005

Inorganica Chimica Acta

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Novel calixarene–Schiff bases that bind silver(I) ion

Creaven¹,

Deasy²,

Flood³

et al. 2008

Inorganic Chemistry Communications

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a b s t r a c tTwo novel calix[4]arene-Schiff base receptors have been synthesized. One of the new compounds has two pendant aldimines, while the second has been prepared by two-point attachment of a calixarenedialdehyde onto a calixarene-diamine to form a ''calix-tube". Preliminary binding studies with AgClO 4 show large complexation-induced shifts in 1 H NMR positions.Ó 2008 Elsevier B.V. All rights reserved.Calixarenes have proved popular building blocks for the development of highly specific synthetic receptors particularly for ionic guest species [1]. They have found widespread use in sensor technology, as sensing agents for various analytes [2]. Calix[n]arenes are macrocyclic compounds in which phenolic units are linked via methylene bridging groups at their ortho positions. The spectacular development of these well defined macromolecular systems in recent years is related to the ease with which the upper (aryl) and lower (phenolic) rims have been modified in a stereocontrolled and regiocontrolled manner [1], coupled with the wide range of cationic [3,4] and neutral [5-7] guests they have been found to bind.The smallest in the series is where four phenolic units make up the macrocyclic backbone (n = 4). This offers a highly rigid platform on which to attach functional groups with potential to act as preorganised binding sites for selective complexation, hence its use by many research groups as a key structural motif for the design and synthesis of an ever increasing number of synthetic receptors [8]. Higher order calix[4]arenes have been designed and synthesised, where either the lower or upper cavity has been bridged by crown [9], azacrown [10] and peptide [11] moieties to expand the range of guests bound. Several double calix[4]arenes (or calix-tubes) [12] have been prepared as additional examples of more complex molecular architectures in the recent past. The attachment of N-ligating groups through imine bond formation has been successful at the upper [13] and lower [14] rim of calixarenes. This has resulted in the formation of calixarene-Schiff base receptors which have shown potential for cation recognition, particularly with the transition metals [15]. Herein we report the efficient syntheses of two new calixarene-Schiff base compounds along with some preliminary binding results. One of the new compounds is a double calixarene (or calix-tube) where the two calixarene units are linked at their lower rims (tail-to-tail) [16]. using imine spacer groups. Both new compounds are distal functionalised calix[4]arenes, i.e. where the 1,3-phenolic H atoms have been replaced. In addition a new calixarene-dialdehyde (calix-dial) template was isolated in the cone conformation.1,3-Substitution on two of the oxygens on the lower rim of calix[4]arene is readily achieved by alkylation, and McKervey has prepared and studied many such derivatives and their binding properties to cations [17]: they typically retain the cone conformation, easily identified by 1 H NMR spectroscopy [18]. Many more recent examples use such me...

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Photocontrol of Complexation of Neutral and Cationic Species by p‐tert‐Butylcalix[4]arene Tetraethyl Ester

Cited by 3 publications

References 26 publications

Coordination chemistry of calix[4]arene derivatives with lower rim functionalisation and their applications

Coordination chemistry of calix[4]arene derivatives with lower rim functionalisation and their applications

Unusual reactivity of copper(I) complexes of functionalised calix[4]arenes

Novel calixarene–Schiff bases that bind silver(I) ion

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