Synthesis and alkali cation extraction ability of 1,3-alt-thiacalix[4]bis(crown) ethers

Grűn, Alajos; Csókai, Viktor; Parlagh, Gyula; Bitter, István

doi:10.1016/s0040-4039(02)00764-5

Tetrahedron Letters

2002

DOI: 10.1016/s0040-4039(02)00764-5

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Synthesis and alkali cation extraction ability of 1,3-alt-thiacalix[4]bis(crown) ethers

Alajos Grűn

Viktor Csókai

Gyula Parlagh

et al.

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Cited by 40 publications

(34 citation statements)

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“…5 We recently reported that thiacalix[4]bis(crown-5 and crown-6) compounds behave as K + and Cs + ion receptors, respectively, but showed a low binding ability, which was proven by Xray crystallography and NMR chemical shift change.…”

mentioning

confidence: 99%

“…5,7 This led us to investigate the oxidation of thiacalix[4]biscrown-5. We report herein the synthetic method and the physical properties and crystal structure of the resulting molecules.…”

mentioning

confidence: 99%

“…4 It was also reported that 1,3-thiacalix [4]mono(crown-5 and crown-6) ethers in the 1,3-alternate conformation could be prepared by condensation of 1,3-dialkoxythiacalix [4]arenes with polyethylene glycol ditosylates or diiodides. 5 We recently reported that thiacalix [4]bis(crown-5 and crown-6) compounds behave as K + and Cs + ion receptors, respectively, but showed a low binding ability, which was proven by Xray crystallography and NMR chemical shift change. 6 Oxidation of the sulfur atoms of the thiacalix [4]arene into sulfinyl and sulfonyl groups, giving novel building blocks that could find many possible applications in supramolecular chemistry, has previously been described.…”

mentioning

confidence: 99%

“…6 Oxidation of the sulfur atoms of the thiacalix [4]arene into sulfinyl and sulfonyl groups, giving novel building blocks that could find many possible applications in supramolecular chemistry, has previously been described. 5,7 This led us to investigate the oxidation of thiacalix [4]biscrown-5. We report herein the synthetic method and the physical properties and crystal structure of the resulting molecules.…”

mentioning

confidence: 99%

“…5 Oxidation of 3 has been carried out using 0. NaBO 3 /AcOH to give monosulfinylcalix [4]biscrown-5 (4) in 33% yield.…”

mentioning

confidence: 99%

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Monosulfinyl Thiacalix[4]biscrown-5 and Its Crystal Structure

Lee¹,

Kim²,

Lee³

et al. 2003

Bulletin of the Korean Chemical Society

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Calixarenes have been used as suitably preorganized building blocks for the construction of more elaborate structures, receptors and molecular assemblies.1 As one of calixarene family, thiacalixarenes having four sulfur atoms instead of methylene bridges have attracted considerable interest as a ligating agent bearing additional coordination sites, modifying the dimensions of the cavity.2 Unlike calix-[4]arenes, thiacalix [4]arenes showed affinity for transition metal ions because the sulfur atoms in the calixarene framework take part in the metal ion complexation. 4 It was also reported that 1,3-thiacalix[4]mono(crown-5 and crown-6) ethers in the 1,3-alternate conformation could be prepared by condensation of 1,3-dialkoxythiacalix[4]arenes with polyethylene glycol ditosylates or diiodides. 5 We recently reported that thiacalix[4]bis(crown-5 and crown-6) compounds behave as K + and Cs + ion receptors, respectively, but showed a low binding ability, which was proven by Xray crystallography and NMR chemical shift change. 6Oxidation of the sulfur atoms of the thiacalix[4]arene into sulfinyl and sulfonyl groups, giving novel building blocks that could find many possible applications in supramolecular chemistry, has previously been described. 5,7 This led us to investigate the oxidation of thiacalix[4]biscrown-5. We report herein the synthetic method and the physical properties and crystal structure of the resulting molecules.In a first step, para-tert-butylphenol was cyclized with sulfur to give para-tert-butylthiacalix [4]

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mentioning

confidence: 99%

“…5,7 This led us to investigate the oxidation of thiacalix[4]biscrown-5. We report herein the synthetic method and the physical properties and crystal structure of the resulting molecules.…”

mentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

“…5 Oxidation of 3 has been carried out using 0. NaBO 3 /AcOH to give monosulfinylcalix [4]biscrown-5 (4) in 33% yield.…”

mentioning

confidence: 99%

See 3 more Smart Citations

Monosulfinyl Thiacalix[4]biscrown-5 and Its Crystal Structure

Lee¹,

Kim²,

Lee³

et al. 2003

Bulletin of the Korean Chemical Society

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Thiacalix[4]‐bis‐crown with Hard Cavities and Soft Bridges Exhibiting Endocyclic Potassium(I) Complexes and Exocyclic Silver(I) Coordination Polymers

Kim

Choi

et al. 2018

Eur J Inorg Chem

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Thiacalix[4]-bis-crown-5 (L) was employed as a model host molecule, which shows both HSAB concept and endo/exo-coordination modes. In the K + complexations, a dinuclear complex [K 2 (L)](ClO 4 ) 2 ·CH 3 CN (1) as well as a mononuclear complex [K(L)][Pt(tht)Cl 5 ] (2) (tht = tetrahydrothiophene) were isolated: the latter as first example in such symmetrical hosts. Each K + in both species is stabilized not only by K + -O bondings (hard acid -hard base) in the crown cavities (endo-coordination) but also by K + -π interactions. The Ag + complexations afforded infinite products (3 and 4) in which the Ag + binds to the sulphur bridges (soft acid -soft base) from outside the cavity [a]

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Chemistry of Thiacalixarenes

2004

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Thiacalixarenes — new members of the calixarene family — are very promising molecules with many potential applications in supramolecular chemistry. The presence of four sulfur atoms in the place of methylene groups imparts many novel features and properties to these molecules. This review deals with the chemistry of thiacalixarenes, and by comparision with “classical” calixarenes, emphasizes their differences in reactivity, unusual conformational preferences and modified complexation abilities. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

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Synthesis and alkali cation extraction ability of 1,3-alt-thiacalix[4]bis(crown) ethers

Cited by 40 publications

References 18 publications

Monosulfinyl Thiacalix[4]biscrown-5 and Its Crystal Structure

Monosulfinyl Thiacalix[4]biscrown-5 and Its Crystal Structure

Thiacalix[4]‐bis‐crown with Hard Cavities and Soft Bridges Exhibiting Endocyclic Potassium(I) Complexes and Exocyclic Silver(I) Coordination Polymers

Chemistry of Thiacalixarenes

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