Effect of Lower‐Rim Alkylation of <i>p</i>‐Sulfonatocalix[4]arene on the Thermodynamics of Host–Guest Complexation

Cui, Jie; Uzunova, Vanya D.; Guo, Dong‐Sheng; Wang, Kui; Nau, Werner M.; Liu, Yu

doi:10.1002/ejoc.200901361

Cited by 41 publications

(33 citation statements)

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“…After the seminal work conducted by the Shinkai research group on the synthesis and aggregation of amphiphilic p -sulfonatocalix[ n ]arenes, these molecules have been sporadically revisited by several researchers, but, to the best of our knowledge, none of these works were focused on the aggregation properties of this special class of surfactants [43–58]. Recently, our group has decided to undertake a systematic study on the self-assembly of such amphiphiles [59–61].…”

Section: Amphiphilic Sulfonatocalixarenes: Structure-aggregation Rmentioning

confidence: 99%

Aggregation of p-Sulfonatocalixarene-Based Amphiphiles and Supra-Amphiphiles

Basílio¹,

Francisco²,

García‐Río³

2013

IJMS

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p-Sulfonatocalixarenes are a special class of water soluble macrocyclic molecules made of 4-hydroxybenzenesulfonate units linked by methylene bridges. One of the main features of these compounds relies on their ability to form inclusion complexes with cationic and neutral species. This feature, together with their water solubility and apparent biological compatibility, had enabled them to emerge as one the most important host receptors in supramolecular chemistry. Attachment of hydrophobic alkyl chains to these compounds leads to the formation of macrocyclic host molecules with amphiphilic properties. Like other oligomeric surfactants, these compounds present improved performance with respect to their monomeric counterparts. In addition, they hold their recognition abilities and present several structural features that depend on the size of the macrocycle and on the length of the alkyl chain, such as preorganization, flexibility and adopted conformations, which make these molecules very interesting to study structure-aggregation relationships. Moreover, the recognition abilities of p-sulfonatocalixarenes enable them to be applied in the design of amphiphiles constructed from non-covalent, rather than covalent, bonds (supramolecular amphiphiles). In this review, we summarize the developments made on the design and synthesis of p-sulfonatocalixarenes-based surfactants, the characterization of their self-assembly properties and on how their structure affects these properties.

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Section: Amphiphilic Sulfonatocalixarenes: Structure-aggregation Rmentioning

confidence: 99%

Aggregation of p-Sulfonatocalixarene-Based Amphiphiles and Supra-Amphiphiles

Basílio¹,

Francisco²,

García‐Río³

2013

IJMS

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“…[4][5][6] 682 FARAJI, FARAJTABAR and GHARIB Most of the beneficial effects of these cyclic oligomers arises from their ability as a suitable host molecule to interact with neutral and ionic species through hydrophobic, π-π, cation-π and hydrogen bonding interactions, especially by their lower rim hydroxyl groups. 2,7 The chemistry of calixarenes is closely related to the nature of their hydroxyl groups at the lower rim. Hydroxyl groups play a major role in conformational flexibility, cavity size and selective binding behavior of calixarenes.…”

Section: Introductionmentioning

confidence: 99%

Ionic strength effect on deprotonation of para-sulfonatocalix[4]arene

Faraji¹,

Farajtabar

Gharib

2013

JSCS

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The deprotonation of para-sulfonatocalix[4]arene were studied by a combination of spectrophotometric and potentiometric methods at 25°C. The ionic strength of solutions was kept constant by sodium perchlorate as background electrolyte at 0.10 to 4.0 mol dm-3. Potentiometer was calibrated according to Gran method for each ionic strength. Spectral changes show evidence for proton dissociation of only one hydroxyl group of calixarene in the studied pH range of 2-10. The pKa values were calculated using STAR program by multivariate curve resolution of absorbance data. Results indicate that the acid-base behavior of para-sulfonatocalix[4]arene varies strongly with increasing ionic strength of solution. The dependence of deprotonation constants on ionic strength were explained by means of Specific ion Interaction Theory (SIT). Activity coefficients of species were modeled by a modified SIT approach. The specific ion interaction parameters were extracted associated with thermodynamic deprotonation constant of para-sulfonatocalix[4]arene

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“…For example, pH-dependent binding of guests is well known for calixarenes [15][16][17] and, in particular, for cucurbiturils (CBs). [18][19][20] CBs have received much attention in recent years, 21 which has led to versatile applications, including the stabilisation of dyes and drugs, 8,13,22 chemosensing and monitoring, 5,23-25 the implementation of logic gates, 20 and the use as nanoreactors.…”

mentioning

confidence: 99%