Thiacalixarenes

Iki, Nobuhiko

doi:10.1007/978-3-319-31867-7_13

Cited by 12 publications

(2 citation statements)

References 92 publications

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“…Calixarenes are products of phenol–aldehyde condensation, as the aromatic components may derived from phenol, resorcinol, or pyrogallol; the aldehyde most often used for phenol is simple formaldehyde (methanal, HCHO), while larger aldehydes (e.g., acetaldehyde – ethanal, CH 3 CHO) are required in condensation reactions with resorcinol and pyrogallol [1]. Thiacalixarenes are macrocycles (or cyclic oligomers) based on a condensation of the same phenol derivatives and sulfur [2]. They are characterized by a larger cavity size than the conventional calixarenes (with the same repeating units).…”

Section: Introductionmentioning

confidence: 99%

Host–guest interactions between p-sulfonatocalix[4]arene and p-sulfonatothiacalix[4]arene and group IA, IIA and f-block metal cations: a DFT/SMD study

Nikolova¹,

Kirkova²,

Angelova³

et al. 2019

Beilstein J. Org. Chem.

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The molecular recognition in aqueous solution is extremely important because most biological processes occur in aqueous solution. Water-soluble members of the calix[n]arene family (e.g., p-sulfonato substituted) can serve as model systems for studying the nature and manner of interactions between biological receptors and small ions. The complex formation behavior of water-soluble p-sulfonatocalix[4]arene and thiacalix[4]arene and group IA, IIA and f-block metal cations has been investigated computationally by means of density functional theory computations in the gas phase and in aqueous environment. The calculated Gibbs free energy values of the complex formation reaction of these ligands with the bare metal cations suggest a spontaneous and energy-favorable process for all metal cations in the gas phase and only for Na+, Mg2+, Lu3+ cations in water environment. For one of the studied cations (La3+) a supramolecular approach with explicit solvent treatment has been applied in the study of the effect of metal hydration on the complexation process. The La3+ binding to the p-sulfonatocalix[4]arene host molecule (now in the metal’s second coordination shell) is still exergonic as evidenced by the negative Gibbs free energy values (ΔG 1 and ΔG 78). The combination of implicit/explicit solvent treatment seems useful in the modeling of the p-sulfonatocalix[4]arene (and thiacalix[4]arene) complexes with metal cations and in the prediction of the thermodynamic parameters of the complex formation reactions.

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Section: Introductionmentioning

confidence: 99%

Host–guest interactions between p-sulfonatocalix[4]arene and p-sulfonatothiacalix[4]arene and group IA, IIA and f-block metal cations: a DFT/SMD study

Nikolova¹,

Kirkova²,

Angelova³

et al. 2019

Beilstein J. Org. Chem.

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“…Heteracalixaromatics − are synthetic macrocycles, which are composed of heteroatoms and meta -(het)arylene in an alternative manner. Being different from conventional calix[4]arenes, nitrogen- and oxygen-bridged calix[4]aromatics reported to date adopt generally 1,3-alternate conformational structures both in crystalline state and in solution .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Structure of Functionalized Homo Heteracalix[2]arene[2]triazines: Effect of All Heteroatom Bridges on Macrocyclic Conformation

Liang

Wang

2018

J. Org. Chem.

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A number of unprecedented homo heteracalix[2]arene[2]triazines were synthesized by means of a fragment coupling approach. Two directional nucleophilic substitution reactions of N-Boc-protected 1,3-dihydrazobenzene with cyanuric acid chloride and 2-butoxy-4,6-dichloro-1,3,5-triazine led to hydrazo-linked trimers, which underwent an efficient macrocyclic condensation reaction with functionalized resorcinol derivatives to afford (NHNBoc),O-calix[2]arene[2]triazine macrocycles, which contain a functional group either on the upper rim or the lower rim. The use of 1,3-phenylenediamines instead of resorcinol in the reaction produced (NR),(NHNBoc)-calix[2]arene[2]triazines. Postmacrocyclization modifications such as a nucleophilic substitution reaction of chloro on triazine by amines and the removal of Boc from hydrazo moieties produced homo calix[2]arene[2]triazine derivatives. In the solid state, (NHNR),O-bridged calix[2]arene[2]triazines with and without a substituent on the upper rim position and (NMe),(NHNBoc)-calix[2]arene[2]triazine adopted a typical partial cone conformation while the heavily twisted 1,3-alternate conformational structures were observed for both (NHNBoc),O-calix[2]arene[2]triazines bearing a functional group on the lower rim position and (NH),(NHNBoc)-calix[2]arene[2]triazine. In solution, all synthesized homo heteracalix[2]arene[2]triazines existed as the mixture of different macrocyclic conformers, which underwent slow interconversions at room temperature relative to the NMR time scale.

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Synthesis of O₆‐Corona[3]arene[3]pyridazines and Their Molecular Recognition Property in Organic and Aqueous Media

Lü

Liang

et al. 2018

Chin. J. Chem.

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O6‐Corona[3]arene[3]pyridazines were synthesized from the one‐pot macrocyclic condensation reaction of 3,6‐dichlorotetrazine with 1,4‐dihydroquinone derivatives followed by the inverse electron demand Diels‐Alder reaction of the tetrazine rings with a cyclopentanone‐derived enamine. Conversion of six ester groups within macrocycle into all sodium acetate moieties afforded a water soluble O6‐corona[3]arene[3]pyridazine. The coronary macrocycle host formed complexes selectively with organic ammoniums and dinitrile guests in a 1: 1 stoichiometric ratio in organic solvents with association constants ranging from (2.96 ± 0.10) × 101 to (2.53 ± 0.33) × 105 L·mol−1. Water soluble O6‐corona[3]arene[3]pyridazine was also able to complex strongly with organic ammoniums in water to give an association constant up to (2.67 ± 0.21) × 104 L·mol−1. The pseudo‐rotaxane and inclusion structures of the host‐guest complexes were revealed by the X‐ray crystallography.

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Thiacalixarenes

Cited by 12 publications

References 92 publications

Host–guest interactions between p-sulfonatocalix[4]arene and p-sulfonatothiacalix[4]arene and group IA, IIA and f-block metal cations: a DFT/SMD study

Host–guest interactions between p-sulfonatocalix[4]arene and p-sulfonatothiacalix[4]arene and group IA, IIA and f-block metal cations: a DFT/SMD study

Synthesis and Structure of Functionalized Homo Heteracalix[2]arene[2]triazines: Effect of All Heteroatom Bridges on Macrocyclic Conformation

Synthesis of O₆‐Corona[3]arene[3]pyridazines and Their Molecular Recognition Property in Organic and Aqueous Media

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Thiacalixarenes

Cited by 12 publications

References 92 publications

Host–guest interactions between p-sulfonatocalix[4]arene and p-sulfonatothiacalix[4]arene and group IA, IIA and f-block metal cations: a DFT/SMD study

Host–guest interactions between p-sulfonatocalix[4]arene and p-sulfonatothiacalix[4]arene and group IA, IIA and f-block metal cations: a DFT/SMD study

Synthesis and Structure of Functionalized Homo Heteracalix[2]arene[2]triazines: Effect of All Heteroatom Bridges on Macrocyclic Conformation

Synthesis of O6‐Corona[3]arene[3]pyridazines and Their Molecular Recognition Property in Organic and Aqueous Media

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Synthesis of O₆‐Corona[3]arene[3]pyridazines and Their Molecular Recognition Property in Organic and Aqueous Media