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Iki, Nobuhiko; Miyano, Sotaro

doi:10.1023/a:1014406709512

Cited by 188 publications

(91 citation statements)

References 18 publications

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“…3,4 Thiacalix [4]arene is an interesting novel member of the calixarene family. 5,6 Unsubstituted thiacalix [4]arene is able to complex various transition metals, due to the presence of the bridging sulfur atoms. 7 The participation of sulfur in the complexation has been observed in X-ray crystal structures of complexes with alkali metal cations.…”

mentioning

confidence: 99%

Cation control on the synthesis of p-t-butylthiacalix[4](bis)crown ethers

Leeuwen¹,

Beijleveld²,

Kooijman

et al. 2002

Tetrahedron Letters

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Abstract-Bridging of p-t-butylthiacalix[4]areneUnsubstituted thiacalix [4]arene is able to complex various transition metals, due to the presence of the bridging sulfur atoms. 7 The participation of sulfur in the complexation has been observed in X-ray crystal structures of complexes with alkali metal cations. 8 The complexation properties of thiacalix[4]arenes can be altered, both by functionalizing the lower rim with ligating sites or by oxidation of the bridging sulfur atoms. With 4 equiv. of Cs 2 CO 3 after 6 h, reaction of 1 with 2 (1.8 equiv.) exclusively afforded the 1,2-alternate thiacalix[4]biscrown-4 4 in 72% yield upon precipitation of the crude reaction mixture with methanol/acetone. Also the reaction of 1 and 3 (1.8 equiv.) with 4 equiv. of base gave a fast reaction (12 h, 100% conversion). The reaction gave a mixture of the 1,2-alternate thiacalix[4]biscrown-5 5 and the corresponding 1,3-alternate isomer 6. The pure thiacalix[4]biscrown-5 isomers 5 (27%) and 6 (15%) were isolated by fractional precipitation from methanol/acetone mixtures. Surprisingly, the proximal thiacalix[4]biscrowns-4 and -5 were only obtained in the 1,2-alternate conformation. The corresponding proximally substituted thiacalix[4]monocrown and proximally substituted cone thiacalix[4]biscrown compounds could not be detected. Compounds 4 and 5 were characterized by NMR ( 1 H and 13 C) and MS. 20,21 Definite proof for the 1,2-alternate thiacalix[4]biscrown-5 5 was obtained by an X-ray crystal structure (Fig. 1).22

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confidence: 99%

Cation control on the synthesis of p-t-butylthiacalix[4](bis)crown ethers

Leeuwen¹,

Beijleveld²,

Kooijman

et al. 2002

Tetrahedron Letters

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“…[1][2][3][4][5][6] Later thiacalix [4]arene, firstly described by Miyano, [7] became a very attractive class of calixarene family that can be tuned to serve as efficient host for different guests either by modulating their conformation or by modifying the nature and number of ligating sites. [8][9][10][11][12][13][14] Attractive features of thiacalix [4]arene scaffold for the design of the host molecules are presented in Figure 1.…”

Section: Introductionmentioning

confidence: 99%

“…[8][9][10][11][12][13][14] In this review, we have focused and highlighted our recent findings of (i) synthesis of lower rim tetrasubstituted derivatives of thiacalixarene, and (ii) design of thiacalixarene-based amphiphilic receptor molecules and their application for the sensing technique.…”

Section: Introductionmentioning

confidence: 99%

Thiacalix[4]arene’s Lower Rim Derivatives: Synthesis and Supramolecular Properties

Solovieva¹,

Burilov²,

Антипин³

2017

MHC

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“…[17][18][19][20][21][22][23][24][25] Thiacalix [4] arenes, analogues of classical calixarenes, are unique in that the initial macrocycles are easily obtained by a onestep synthesis, [18,25] their sulfide bridge fragments easily coordinates transition metal cations, [16] whiles the upper and lower rims are easily functionalized. [18,25] In addition, they exist in variable conformations [19][20][21] hence they offer different spatial arrangement of functional groups, a prerequisite for molecular recognition. Previously, it was shown that p-tert-butylthiacalix [4]arenes functionalized by N-propyl morpholine, N,N-dipropyliden-amine and aminodiacetate fragments interacted with the polar domains of model lipid membranes.…”

Section: Introductionmentioning

confidence: 99%