2014
DOI: 10.1039/c4cs00068d
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Recent developments of thiacalixarene based molecular motifs

Abstract: Thiacalixarenes, a subclass of "third generation" calixarenes, exhibit many interesting features such as enlarged ring size, facile chemical modification, and metal complexation due to the presence of bridging sulfur atoms. The thiacalixarene scaffold is a unique host with vast possibilities for functionalization not only at the upper and lower rim but also at the bridging sulfide groups. Modified thiacalixarenes have been used for many applications such as the detection and separation of biologically importan… Show more

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Cited by 250 publications
(143 citation statements)
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References 257 publications
(521 reference statements)
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“…Reaction of 1 and 2 with simple alkyl halides (RI or RBr, R>C 3 H 7 ) in the presence of base generally gives the tetraalkylated products in 1,3-alternate conformation. [9,10,13] In the case of electrophilic reagents containing n-donor Thiacalix [4]arene's Lower Rim Derivatives groups, [9,10,13,[18][19][20] Easily available by the Newman-Kwart rearrangement tetramercaptothiacalix [4]arene 67 [57] adopting 1,3-alternate conformation [58] undergoes easily base-catalyzed etherification with the formation of carboxyl, pyrazolyl, [31] cyanopropoxy, [59] cyanobenzyloxy [59] and α, β, γ pyridylmethoxy [60] derivatives 6871 (Scheme 3).…”
Section: Synthesis Of Tetrasubstituted Thiacalix[4]arene Derivativesmentioning
confidence: 99%
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“…Reaction of 1 and 2 with simple alkyl halides (RI or RBr, R>C 3 H 7 ) in the presence of base generally gives the tetraalkylated products in 1,3-alternate conformation. [9,10,13] In the case of electrophilic reagents containing n-donor Thiacalix [4]arene's Lower Rim Derivatives groups, [9,10,13,[18][19][20] Easily available by the Newman-Kwart rearrangement tetramercaptothiacalix [4]arene 67 [57] adopting 1,3-alternate conformation [58] undergoes easily base-catalyzed etherification with the formation of carboxyl, pyrazolyl, [31] cyanopropoxy, [59] cyanobenzyloxy [59] and α, β, γ pyridylmethoxy [60] derivatives 6871 (Scheme 3).…”
Section: Synthesis Of Tetrasubstituted Thiacalix[4]arene Derivativesmentioning
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%
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“…The relative simplicity of functionalization together with the possibility of pre-determination of the macrocycle configuration by various spatially fixed functional groups led to development of variety of the systems able to recognize various substrates, both neutral and ionic, and their application in the sensor devices. [10][11][12][13][14][15][16][17][18][19][20] Covalent binding of oligolactic acid to the tetracarboxylic derivatives of p-tert-butylthiacalix [4]arene, which were in three spatial conformations (cone, partial cone and 1,3-alternate) allowed obtaining novel polymer materials for modification of the glassy carbon electrode surface. [21] Compounds synthesized were found to be promising for design of the sensor devices for recognition of some low-molecular biologically relevant analytes.…”
Section: Introductionmentioning
confidence: 99%
“…[24][25][26] The chemistry of thiacalixarene is interesting because it can bind metal ions by sulfur bridges, which is not possible with normal calixarenes. 24,26 Since two thiacalixarene molecules are bridged upon binding to metal ions, [27][28][29] we hypothesized that AgNPs coated with thiacalixarene could be bridged by metal complexation, and lead to the colorimetric sensing of metal ions.…”
Section: Introductionmentioning
confidence: 99%