A novel host molecule p-[1-(4-hydroxyphenyl)-1-methylethyl]calix[8]arene. Synthesis and complexation properties in non-aqueous polar solution

Tung, Chen‐Ho; Ji, Hai‐Feng

doi:10.1039/a606270i

Cited by 11 publications

(4 citation statements)

References 26 publications

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“…Despite the extended use of this family of compounds as hosts for inclusion complex formation, calixarenes have received much less attention from photochemists when compared with other host molecules of practical importance, even in solution studies. Very few photochemical studies of organic compounds within calixarenes were presented. − …”

Section: Introductionmentioning

confidence: 99%

A Diffuse Reflectance Comparative Study of Benzil Inclusion within p-tert-Butylcalix[n]arenes (n = 4, 6, and 8) and Silicalite

et al. 2002

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Diffuse reflectance and laser-induced techniques were used to access photochemical and photophysical processes of benzil in solid supports, namely p-tert-butylcalix[n]arenes with n = 4, 6, and 8. A comparative study was performed using these results and those obtained with another electronically inert support, silicalite, which is a hydrophobic zeolite. In the latter substrate, ground-state benzil has the two carbonyl groups in an s-trans planar conformation while in the calixarenes a distribution of conformers exists, largely dominated by skew conformations where the carbonyl groups are twisted one to the other. In all substrates, room-temperature phosphorescence was obtained in air-equilibrated samples. The decay times vary greatly and the largest lifetime was obtained for benzil/p-tert-butylcalix[6]arene, showing that this host cavity well accommodates benzil, enhancing its room-temperature phosphorescence. p-tert-Butylcalix[6] and [8]arene molecules provide larger hydrophobic cavities than silicalite, and inclusion complexes are formed with these hosts and benzil as guest; p-tert-butylcalix[4]arene does not include benzil. This probe is deposited outside the calix[4] cavity, in the form of microcrystals. Triplet−triplet absorption of benzil was detected in all cases and is predominant in the silicalite channel inclusion case. Benzil ketyl radical formation occurs with inclusion in calix[6]arene and calix[8]arene. In the three cases, benzoyl radical was detected at long times (in the millisecond time scale). Product analysis and identification clearly show that the main detected degradation photoproducts in all substrates are benzoyl radical derivatives. Calix[6] and [8]arenes are able to supply hydrogen atoms that allow also another reaction, the reduction to benzoin through benzil ketyl radical formation.

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Section: Introductionmentioning

confidence: 99%

A Diffuse Reflectance Comparative Study of Benzil Inclusion within p-tert-Butylcalix[n]arenes (n = 4, 6, and 8) and Silicalite

et al. 2002

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“…In this case, this calixarene compound capable to clamp the organic molecules. Calixarene compounds can be synthesized and derivatized at the "Lower Rim", therefore the part of upper rim calixarene rim is slow to develop [7]. Some type of adsorbent has been used to eliminate or reduce heavy metals, i.e.…”

Section: Introduction:-mentioning

confidence: 99%

Study of Pb(ii) and Fe(iii) Metal Cations Adsorption Into P-Tert-Butylcalix[4]arene as Adsorbent: Kinetic Adsorption.

Busroni¹,

Siswanta²,

SantosaS³

et al. 2017

IJAR

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This research explain the study about compound of 5,11,17,26,27,arene (TBCA) that will be used as adsorption material for heavy metal cations. Adsorption using immersion method with variations such as the value of acidity (pH), time of exposure and initial concentration of metal cations have been conducted. The results of each investigation showed that the optimum pH of adsorption was at pH = 5 for metal cations of Pb(II) and Fe (III). The observation results showed the optimum time exposure of cation adsorption of Pb(II) and Fe(III) was 90 minutes. Study about kinetic adsorption of Pb(II) metal cations of the adsorbent refered the Ho kinetic model, pseudo second order with rate constant of adsorption 143x10 -3 g.mol -1 .min -1 and Fe(III) refered the Lagergren kinetics model, pseudo first order with the rate constant of 9.21 x 10 -3 min -1 . The observation of the study showed that the isotherms adsorption for metal cations of Pb(II) and Fe(III) refered the pattern trend of Langmuir isotherm models. The value of the optimum capacity for metal cation adsorption Pb(II) and Fe(III) each was 128.46 mg/g and 156.09 mg/g respectively. Adsorption energy for Pb(II) and Fe(III) was 5.81 k.J/mol and 7.01 kJ / mol, respectively. …………………………………………………………………………………………………….... Introduction:-The existence of the metal cations can endanger human health as heavy metals if enter into the body, because the heavy metals are toxic/poison. Heavy metals are chemical elements with a specific gravity greater than 5 g/cm 3 that located in the lower right corner of the periodic table system. Iron or Ferrum (Fe) is a silvery-white metal, clay, and can be formed. It has been conducted a study of adsorption of metal cations Fe(III) in aqueous systems using zeolite, in the determination of adsorption of metal cations Fe +3 performed at pH area between 1-6 [1]. Lead was widely used in the paint factory, fuel, battery industry and ammunition bullets. Lead is toxic which very influenced toward children, because the paint is widely used in residences. If the metal contains in the blood up to 10 mg/mL, it can cause illness symtoms and Pb(II) concentrations in the water does not depend on the season, but on the depth. Lead ions contained in the water can get into the body of the fish and other aquatic animals [2]. Siswanta research resulted that the adsorbent Calix[4]resorcinarene, hybrid or Calix[4]resorcinarene-chitosan and chitosan can be applied to eliminate the Pb(II) metal ions. The results of the investigation explained that the value of adsorption capacity was Calix[4]resorcinaren > Chitosan > Calix [4] resorcinarene-chitosan (hybrid) [3]. Prabawati, reported that it can be synthesized compounds of p-t.butyl-37-monoallyloxy-38,39,40,41,42-pentahidroxycalix[6]arene and p-t.butyl-

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“…Among those we quote the relevant report of the photophysical properties of the calix[8]arene-C 60 inclusion complex in the solid state [44], the diffuse reflectance laser flash-photolysis study of BZP and xanthone within calix[6]arene solid matrices [45] and also aqueous and non-aqueous [38,46,47] solution studies of several polycyclic aromatic compounds included within different calix[8]arenes. In the latter cases, inclusion complex formation was detected by pronounced fluorescence enhancement of the guests upon inclusion.…”

Section: Introductionmentioning

confidence: 99%

“…The ability of calixarenes to form inclusion complexes, accommodating guest molecules or ions in their intramolecular cavities, greatly depends on the size and geometry of both guest molecule and host cavity [36][37][38]. In fact, experiments carried out with some polycyclic aromatic hydrocarbons possessing different dimensions and p-(diallylaminomethyl)calixarenes and p-(carboxyethyl)calixarenes showed that calix [4]arenes are too small to accept naphthalene and calix[8]arenes apparently are too small to accept coronene and decacyclene but sufficient to accommodate durene, naphtalene, anthracene, phenanthrene, fluoranthene, pyrene and perylene [37].…”

Section: Introductionmentioning

confidence: 99%

Surface Photochemistry: Organic Molecules within Nanocavities of Calixarenes

Ferreira¹,

Machado²

2007

CDDT

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In order to gain more information regarding photochemical processes in heterogeneous environments (opaque or powdered samples) laser induced time resolved luminescence and diffuse reflectance transient absorption spectroscopies were used for the study of benzophenone (and other neutral organic molecules) as guests and p-tert-butylcalix[n]arenes with n = 4, 6 and 8 (H(n)CLX[n]) and partially or totally O-propylated p-tert-butylcalix[4]arenes (H(n)Pr(m)CLX[4], n = 2, 1 and 0; m = 2, 3 and 4, respectively) were used as hosts. One of the main conclusions was that the solid support can deeply affect or even control the photochemistry of an adsorbed probe. A simple new methodology for lifetime distribution analysis of the decay of the probes included into calixarenes and other nanocavities was applied with success for decay data obtained with the use of intensified charge couple devices, i.e. intensified charge couple devices, ICCDs. Diffuse reflectance laser flash photolysis and gas chromatography - mass spectrometry techniques also provided complementary information, the former about transient species and the latter regarding the final products formed after light absorption.

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A novel host molecule p-[1-(4-hydroxyphenyl)-1-methylethyl]calix[8]arene. Synthesis and complexation properties in non-aqueous polar solution

Cited by 11 publications

References 26 publications

A Diffuse Reflectance Comparative Study of Benzil Inclusion within p-tert-Butylcalix[n]arenes (n = 4, 6, and 8) and Silicalite

A Diffuse Reflectance Comparative Study of Benzil Inclusion within p-tert-Butylcalix[n]arenes (n = 4, 6, and 8) and Silicalite

Study of Pb(ii) and Fe(iii) Metal Cations Adsorption Into P-Tert-Butylcalix[4]arene as Adsorbent: Kinetic Adsorption.

Surface Photochemistry: Organic Molecules within Nanocavities of Calixarenes

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