Synthesis of acridinyl- and fluorenylidenehydrazido derivatives of p-tert-Butylcalix[4]arene

Алексеева, Е. А.; Lyakhova, E. A.; Karpenko, Alexander S.; Luk’yanenko, A. P.; Gren, A. I.

doi:10.1134/s1070363207060199

Cited by 5 publications

(2 citation statements)

References 7 publications

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“…For this purpose, p-tert-butylcalix [4] arene 1, and its diester derivative 2, were synthesized according to the literature procedures [28,29]. The functionalization of the diester derivative 2 at the lower rim was conducted with hydrazine to produce 5,11,17,23-tetra-tert-butyl-25,27-dihydrazinamidecar bonylmethoxy-26,28-dihydroxy-calix [4]arene (3) according to the literature [30]. Next, 3 was treated with ferrocene carboxaldehyde to produce a target calixarene-organoiron derivative 4 (Scheme 1).…”

Section: Selectively Synthesis Of Calixarene Containing Organoiron Dementioning

confidence: 99%

Preparation of the ferrocene-substituted 1,3-distal p-tert-butylcalix[4]arene based QCM sensors array and utilization of its gas-sensing affinities

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Özbek

Okur

2014

Journal of Organometallic Chemistry

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a b s t r a c tThe article describes the synthesis of the new ferrocene-substituted calix [4]arene derivative 4 as sensitive layer, and suggests that the immobilization of it is on a quartz crystal microbalance gold electrode via the drop-casting method in order to produce the calix[4]arene-based QCM sensor. In addition, sensor response of the calix[4]arene-based QCM sensor was investigated towards carbon dioxide (CO 2 ) and carbon monoxide (CO). The sensing and selectivity studies show that the ferrocene-substituted calix [4] arene-based QCM sensor is an effective gas sensor toward both carbon dioxide and carbon monoxide.

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Section: Selectively Synthesis Of Calixarene Containing Organoiron Dementioning

confidence: 99%

Preparation of the ferrocene-substituted 1,3-distal p-tert-butylcalix[4]arene based QCM sensors array and utilization of its gas-sensing affinities

Sayın

Özbek

Okur

2014

Journal of Organometallic Chemistry

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“…In particular, functionalization of macrocyclic compounds with hydrazide and hydrazone groups gives rise to potential biologically active substances [6-8] and highly efficient extractants for transition metal ions [9, 10]; in addition, other nitrogen-containing compounds may be obtained on the basis of functionalized calix[n]arenes [11,12]. For example, by condensation of hydrazides with aldehydes we previously synthesized acetylhydrazone derivatives of calix[4]resorcinol [13], which ensured highly efficient binding of transition metal ions and showed especially high selectivity in the extraction of toxic mercury ions.…”

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confidence: 99%

Synthesis of new hydrazones based on tetrathiacalix[4]arene in the 1,3-alternate conformation

et al. 2010

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Reactions of 1,3-alternate stereoisomers of tetrathiacalix [4]arene and 4-tert-butyltetrathiacalix[4]-arene, functionalized by hydrazide groups, with benzaldehyde and pyridin-2-carbaldehyde gave new tetrathiacalix[4]arene tetrahydrazone derivatives as promising receptors for transition and toxic heavy metal ions.Molecular design of artificial receptors is one of the most important problems in modern chemistry [1,2]. To perform the simplest receptor function, i.e., recognition of one or another substrate, several preorganized coordination centers should be present in a receptor molecule. A convenient base structure for the design of such molecules is provided by calix [n]arenes that are compounds with three-dimensional spatially organized structures [3][4][5].Functionalization of calix[n]arenes could considerably extend the scope of their practical application. In particular, functionalization of macrocyclic compounds with hydrazide and hydrazone groups gives rise to potential biologically active substances [6-8] and highly efficient extractants for transition metal ions [9, 10]; in addition, other nitrogen-containing compounds may be obtained on the basis of functionalized calix[n]arenes [11,12]. For example, by condensation of hydrazides with aldehydes we previously synthesized acetylhydrazone derivatives of calix[4]resorcinol [13], which ensured highly efficient binding of transition metal ions and showed especially high selectivity in the extraction of toxic mercury ions. However, analogous reaction with aldehydes of tetrathiacalix-[4]arene in the cone conformation resulted in preferential formation of bis-acetylhydrazone calix[4]arene derivatives with intramolecular N,N′-diacetylhydrazine bridge [14,15]. The target tetrahydrazone was isolated only in the reaction with pyridine-2-carbaldehyde. Presumably, unusual behavior of the cone conformer is determined by spatial proximity of the endo-oriented hydrazide groups. We presumed that the target tetrahydrazones could be obtained using 1,3-alternate conformer of calix[4]arene. The synthesis of such derivatives was also stimulated by the fact that 1,3-alternate conformers of calix[4]arenes are generally more selective receptors for metal ions. This was observed by us previously for tetrahydrazide derivatives [16]. The use of tetrathiacalix[4]arene scaffold (rather than classical calix[4]arene structure) seemed to be preferred due to simpler preparation of the macrocyclic compound in a required conformation. Apart from 4-tert-butyltetrathiacalix[4]arene derivatives, it was interesting to synthesize their analogs with distant tert-butyl groups. Enhanced flexibility of a receptor molecule and reduction of steric hindrances to coordination with metal ions could favor their more efficient binding.In the present communication we report on the synthesis of acetylhydrazone tetrathiacalix[4]arene and 4-tert-butyltetrathiacalix[4]arene derivatives having 1,3-alternate conformation (Scheme 1). In the first step, tetraesters Ia and Ib were synthesized by reactions of unsubsti...

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A study on thermal behaviors of mono ethyl ester azocalix[4]arene derivatives

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et al. 2014

J Therm Anal Calorim

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Synthesis of acridinyl- and fluorenylidenehydrazido derivatives of p-tert-Butylcalix[4]arene

Cited by 5 publications

References 7 publications

Preparation of the ferrocene-substituted 1,3-distal p-tert-butylcalix[4]arene based QCM sensors array and utilization of its gas-sensing affinities

Preparation of the ferrocene-substituted 1,3-distal p-tert-butylcalix[4]arene based QCM sensors array and utilization of its gas-sensing affinities

Synthesis of new hydrazones based on tetrathiacalix[4]arene in the 1,3-alternate conformation

A study on thermal behaviors of mono ethyl ester azocalix[4]arene derivatives

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