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

Creaven, Bernadette S.; Donlon, Denis F.; McGinley, John

doi:10.1016/j.ccr.2008.06.008

Cited by 201 publications

(147 citation statements)

References 287 publications

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“…There are many literature reports of distal 1,3-bis(amido)-linked calix [4]arenes with a variety of ligating groups for binding to neutral, anionic and cationic guests [3][4][5][6]. In the vast majority of these cases the ligating groups have a large degree of conformational freedom.…”

Section: Synthesismentioning

confidence: 99%

“…Literature syntheses of amide linked calix [4]arenes have mainly used three different methods to create the amide linker [3][4][5][6]. Firstly, aminolysis of an ester with an amine gave good yields of the amides, but this method is restricted to the use of primary amines.…”

Section: Figurementioning

confidence: 99%

“…Much of the current research into calixarenes focuses on the smallest and most rigid of the family, namely the calix [4]arenes, since the larger cavity-containing analogues are more flexible and therefore not always suited to strong binding with guest species, and are also generally less selective. Many calix [4]arene compounds have been synthesised over the last 40 years, with a variety of ligating groups to fine-tune binding to an array of ionic and neutral guests in solution and in the solid state [3][4][5][6]. Some of the functionalities attached to the calixarene scaffold are large and while they can facilitate binding can crowd the cavity and decrease the binding strength.…”

Section: Introductionmentioning

confidence: 99%

“…Calix [4]arenes are an important class of macrocyclic compounds which have been used extensively in supramolecular chemistry for molecular recognition [3][4][5][6]. They were first prepared by Baeyer in 1872, as by-products in the synthesis of baeklite [7].…”

Section: Introductionmentioning

confidence: 99%

“…Since Gutsche first published the synthesis of calix [4]arene-based macrocycles [11], the investigation of the complexation properties of these compounds has been of intense interest for a wide variety of ionic species and small organic guest molecules, through the formation of host-guest or supramolecular complexes. This area is subject to regular in-depth reviews [3][4][5][6].…”

Section: Introductionmentioning

confidence: 99%

See 4 more Smart Citations

Bis(spirolactam) 1,3-double-armed calix[4]arene compounds and their application as extractants for the determination of heavy metal ions

Ward

Regan

et al. 2015

J Incl Phenom Macrocycl Chem

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Section: Synthesismentioning

confidence: 99%

Section: Figurementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Bis(spirolactam) 1,3-double-armed calix[4]arene compounds and their application as extractants for the determination of heavy metal ions

Ward

Regan

et al. 2015

J Incl Phenom Macrocycl Chem

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Calixarenes in Molecular Recognition

Baldini¹,

Sansone²,

Casnati³

et al. 2012

Supramolecular Chemistry

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This chapter summarizes the most important aspects of the chemistry of calixarenes and their applications in supramolecular chemistry. The first section gives a short summary of the synthesis and conformational properties of calixarenes and of their functionalization at the phenolic OH groups ( lower rim ) and at the para‐position of the aromatic nuclei ( upper rim ). The second section covers the properties of native and functionalized calixarenes (including chiral compounds) as receptors for the selective recognition of neutral molecules, cations, anions, and ion‐pairs in the solid state, organic media, and water solution. In the third section, the calixarenes are viewed as scaffolds for the construction of multivalent ligands able to target biomacromolecules eliciting or inhibiting a biological process. Calixarene glycoclusters, operating as efficient and selective multivalent inhibitors of vegetal and mammalian lectins; peptidocalixarenes, capable of disrupting protein–protein interactions; and guanidino‐calixarenes, able to target proteins or to condense DNA, acting, in this case, as efficient nonviral vectors for cell transfection, are discussed. When relevant, the use of calixarene receptors and multivalent ligands as active components of sensor devices for the detection of various analytes is also reported. Perspectives for future developments of calixarenes in supramolecular chemistry and bionanotechnology are indicated.

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