Synthesis and Inclusion Properties ofC3-Symmetrically Capped Hexahomotrioxacalix[3]arenes with Ester Groups on the Lower Rim

Yamato, Takehiko; Zhang, Fenglei; Tsuzuki, Hirohisa; Miura, Yoshinori

doi:10.1002/1099-0690(200103)2001:6<1069::aid-ejoc1069>3.0.co;2-r

Cited by 30 publications

(20 citation statements)

References 35 publications

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“…Ionophore properties of rigid molecules 64 and 65 with respect to metal and ammonium cations were investigated in [50,51]. The rigidity of molecules was achieved by capping the lower rim of oxacalixarenes.…”

Section: Receptor Properties Of Hexahomotrixacalix[3]arenas Derivativmentioning

confidence: 94%

“…Ionophore properties of oxacalixarene 65 were studied by extraction from the water phase into CH 2 Cl 2 [50]. For comparison a related oxacalixarene 67 was used.…”

Section: Receptor Properties Of Hexahomotrixacalix[3]arenas Derivativmentioning

confidence: 99%

“…b Solvent THF-d 8 CDCl 3 , in other cases THF-d 8 . [50]. The special interest of this study lies in the fact of the presence of BuNH 3 + structural units in biologically important systems.…”

Section: Receptor Properties Of Hexahomotrixacalix[3]arenas Derivativmentioning

confidence: 99%

“…The special interest of this study lies in the fact of the presence of BuNH 3 + structural units in biologically important systems. The resuts obtained suggested [50] that in the arising complexes the EtNH 3 + , ion is located deep in cavity of ligand 65, the MeNH 3 + , ion is on the edge of the cavity, and the alkyl chain length of the BuNH 3 + , ion is already sufficient for protruding from the calixarene cavity. In the complex of BuNH 3 + , with oxacalixarene 65 the protons of NH 3 group interact with three C=O groups and phenol oxygens, whereas the butyl chain is located in the cavity formed by benzene rings.…”

Section: Receptor Properties Of Hexahomotrixacalix[3]arenas Derivativmentioning

confidence: 99%

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Homooxacalixarenes: II. Receptor properties

Shokova

Ковалев

2004

Russ J Org Chem

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Section: Receptor Properties Of Hexahomotrixacalix[3]arenas Derivativmentioning

confidence: 94%

“…Ionophore properties of oxacalixarene 65 were studied by extraction from the water phase into CH 2 Cl 2 [50]. For comparison a related oxacalixarene 67 was used.…”

Section: Receptor Properties Of Hexahomotrixacalix[3]arenas Derivativmentioning

confidence: 99%

Section: Receptor Properties Of Hexahomotrixacalix[3]arenas Derivativmentioning

confidence: 99%

Section: Receptor Properties Of Hexahomotrixacalix[3]arenas Derivativmentioning

confidence: 99%

See 2 more Smart Citations

Homooxacalixarenes: II. Receptor properties

Shokova

Ковалев

2004

Russ J Org Chem

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“…16) Hydrolysis of 3 with KOH gave 7 in 91% yield. 17) Finally, esterification of 7 with ethyl iodide in the presence of 1,8-diazabicyclo [5.4.0]undec-7-ene (DBU) gave 2 in 67% yield. 18) On the other hand, when the reaction was conducted in the presence of sodium, potassium, cesium carbonate, or triethylamine, 2 was produced in <18% yield.…”

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confidence: 99%

The Effects of O-Substituents of Hexahomotrioxacalix[3]arene on Potentiometric Discrimination between Dopamine and Biological Organic/Inorganic Cations

Saijo

Murakami

Tsunekawa

et al. 2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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A variety of methods for the determination of catecholamines (dopamine, noradrenaline, and adrenaline) and their metabolites in biological media have been proposed. Catecholamines are especially important because they are involved in many human physiological and biochemical processes. 1,2) Catecholamines are typically determined by HPLC analysis with electrochemical detection. [3][4][5][6] In most cases, the preliminary extraction and purification of catecholamines from biological samples are necessary. On the other hand, the direct potentiometric determination of catecholamines is extremely attractive. However, the development of ion-selective electrodes for catecholamines is difficult, considering their similar structures and relatively hydrophilic nature. Only a few reports of the potentiometric determination of catecholamines have appeared in the literature. [7][8][9][10] For the development of sensory elements for dopamine, we focused on the hexahomotrioxacalix[3]arene skeleton, which contains both ethereal and phenolic oxygens, both of which are capable of forming tripodal hydrogen bonds with the protonated primary amino group of dopamine. It has been reported that the hexahomotrioxacalix[3]arene host 1 (cone conformer), 11) when incorporated into a poly(vinyl chloride) (PVC) liquid membrane displays a high selectivity for dopamine in membrane potential changes, compared to other catecholamines (noradrenaline and adrenaline) and inorganic cations (Na ϩ and K ϩ ). 7)Guest-induced changes in membrane potential at the membrane without hosts are reflected in only the guest lipophilicity factor. On the other hand, changes in a host are reflected in two factors, i.e., the guest lipophilicity factor and the hostguest complexation factor. Mi and Bakker 12) and Ceresa and Pretsch 13) recently reported on the determination of the hostguest complexation factor (complex formation constants) in PVC membranes to characterize the binding capability of ionophores. We present here a quantitative analysis of the two factors that contribute to dopamine selectivity, in an attempt to better understand the effects of the O-substituents of hexahomotrioxacalix[3]arene hosts 2-5 (Fig. 1). The hostguest complexation factor in PVC membranes constitutes very important information for the further development of sensory elements for dopamine. As an interesting type of molecular recognition at a membrane surface, the tri-O-acetic acid ester (host 2) of hexahomotrioxacalix[3]arene, when incorporated into poly(vinyl chloride) (PVC) liquid membranes, displays a high potentiometric selectivity for dopamine over, not only other catecholamines (noradrenaline, adrenaline), but also quaternary ammonium guests (tetramethylammonium, choline, and acetylcholine) and inorganic cations (Na Results and Discussion Synthesis of Host Molecules). Interestingly, changes in membrane potential based on the host-guest complexation of host 2 that were observed dopamine/inorganic cation selectivity were not displayed by the related hosts 3 and 4, which contain ...

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Nonlinear Optical Properties in Calix[n]arenes: Orientation Effects of Monomers

Datta

Pati

2005

Chemistry A European J

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We investigate the nonlinear optical (NLO) polarizations for various geometric arrangements of the dipolar chromophores in a calix[n]arene geometry. The interactions were studied by using (HF)3 as model compounds both in parallel and frustrated orientations. The interdipolar angle between the monomer molecules is varied so that many different arrangements of the dipoles can be realized which is associated with the opening up of the calix[n]arene rings. Quantum-chemical calculations at both ab initio and semiempirical levels, show that the all-parallel arrangement of the dipoles exhibit the maximum magnitude for the nonlinear optical coefficients at small interdipolar angles for all interdipolar distances. In the frustrated orientations however, the NLO response is maximum at large interdipolar angles corresponding to the flattened calix[n]arene rings. The role of hydrogen bonding in stabilizing these assemblies in various conformations has been investigated. Crystallographic database analysis for calix[3]arenes shows that optical properties in real molecular systems can be modeled based on our simple interaction theory.

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Synthesis and Inclusion Properties ofC3-Symmetrically Capped Hexahomotrioxacalix[3]arenes with Ester Groups on the Lower Rim

Cited by 30 publications

References 35 publications

Homooxacalixarenes: II. Receptor properties

Homooxacalixarenes: II. Receptor properties

The Effects of O-Substituents of Hexahomotrioxacalix[3]arene on Potentiometric Discrimination between Dopamine and Biological Organic/Inorganic Cations

Nonlinear Optical Properties in Calix[n]arenes: Orientation Effects of Monomers

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