The difference between the aggregates of short-tailed and long-tailed cationic calix[4]arene in water as detected using fluorescein dyes

Cheipesh, Tatyana A.; Zagorulko, E.S.; Mchedlov‐Petrossyan, Nikolay O.; Rodik, Roman V.; Kаlchеnkо, Vitaly I.

doi:10.1016/j.molliq.2013.12.049

Cited by 13 publications

(7 citation statements)

References 28 publications

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“…The aggregation properties of two cationic calixarenes with propyloxy ( 164A ) or octyloxy ( 164B ) chains on their lower rims (Figure ) were investigated by the encapsulation of fluorescein dyes . Both calixarenes formed positively charged aggregates with similar zeta potentials.…”

Section: Calix[4]arene-based Receptorsmentioning

confidence: 99%

“…The aggregation properties of two cationic calixarenes with propyloxy (164A) or octyloxy (164B) chains on their lower rims (Figure 34) were investigated by the encapsulation of fluorescein dyes. 298 Both calixarenes formed positively charged aggregates with similar zeta potentials. Octyloxy calixarene 164B was found to have a substantially lower critical aggregation concentration and formed aggregates 1.5 times larger than those of 164A.…”

Section: Chemical Reviewsmentioning

confidence: 99%

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Revisiting Fluorescent Calixarenes: From Molecular Sensors to Smart Materials

et al. 2019

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Calix[n]arenes (n = 4, 5, 6, 8) are "chalicelike" phenol-based macrocycles that are among the most fascinating and highly studied scaffolds in supramolecular chemistry. This stems from the functional and tunable diversity at both their upper and lower rims, their preorganized nonpolar cavities and preorganized ionbinding sites, and their well-defined conformations. Conjugation of calixarene scaffolds with various fluorogenic groups has led to the development of smart fluorescent probes that have been utilized as molecular sensors, in bioimaging, for drug and gene delivery, in self-assembly/aggregation, and as smart materials. The fine-tuning and incorporation of different ligating sites in the calix[4]arene scaffold have produced numerous molecular sensors for cations, anions, and biomolecules. Moreover, the aqueous solubility of p-sulfonatocalix[4]arenes has engendered their potential use in drug/gene delivery and enzymatic assays. In addition, because of their strong optical properties, fluorescent calix[4]arenes have been used to develop smart materials, including gels as well as nonlinear optical, organic light-emitting diode, and multiphoton materials. Finally, significant developments in the utility of fluorescent higher calixarenes have been made for bioapplications. This review critically summarizes the recent advances made in all of these different areas.

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Section: Calix[4]arene-based Receptorsmentioning

confidence: 99%

Section: Chemical Reviewsmentioning

confidence: 99%

Revisiting Fluorescent Calixarenes: From Molecular Sensors to Smart Materials

et al. 2019

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“…Am inor redshift was observed for the fluorescence spectra as well. The absorptiona nd fluorescences pec-tra of free and PEC-linked fluorescein substantially differ in the region of the peak shoulder.T he reason for this variation in the spectra is typically attributed to the different protonation of free [12,18] and bound [19,20] dye forms.T he spectra of free and PEC-linked rhodamine6Gd emonstrate similarshapes.…”

Section: Absorption and Fluorescence Spectramentioning

confidence: 99%

Synthesis and Characterization of Chitosan‐Based Polyelectrolyte Complexes Doped with Xanthene Dyes

et al. 2015

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Biocompatible chitosan-based polyelectrolyte complexes (PECs) doped with xanthene dyes (fluorescein, eosin Y, erythrosin B, rhodamine 6G) were synthesized and characterized by scanning electron microscopy, dynamic light scattering, zeta potential measurements, and absorption and luminescence (including polarized, time-resolved, and phosphorescence) spectroscopy. The results are discussed in terms of the mechanism and rigidity of dye-PEC binding, the heavy-atom effect in dyes and PEC stability. Eosin Y is found to be the optimal dopant, providing both a high dye content in PECs and a high quantum yield of fluorescence.

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“…The H2Z ± tautomer was observed mainly for fluorescein in water [7,57,61]. The fraction of the H2Q tautomer decreases while that of H2L increases on going from water to organic solvents [13,30,37,[39][40][41]57,60] or different kinds of organized solutions, such as micellar solutions of colloidal surfactants [7,13,16,17,39], direct or reversed microemulsions [15,39,62], solutions of dendrimers [63], calixarenes [64], and cyclodextrins [65]. Monoanions HR − of HQ − type are usually observed for fluorescein and its derivatives bearing halogen atoms in the phthalic acid residue [15,62] In the case of alkyl fluorescein, alkyl eosin, and some other model compounds the ionization occurs in two steps.…”

Section: Detailed Scheme Of Protolytic Equilibria In the Micellar Psementioning

confidence: 99%

Protolytic Equilibria in Organized Solutions: Ionization and Tautomerism of Fluorescein Dyes and Related Indicators in Cetyltrimethylammonium Chloride Micellar Solutions at High Ionic Strength of the Bulk Phase

Mchedlov‐Petrossyan

Vodolazkaya

2021

Liquids

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Ionic equilibrium of 22 hydroxyxanthenes, including halogen and nitro derivatives of fluorescein, and their thio- and aza analogues, were studied spectrophotometrically in micellar solutions of cetyltrimethylammonium chloride at ionic strength of the bulk phase 4.0 M KCl. This micellar pseudophase is characterized by the electrostatic surface potential of +(15–16) mV and the ETN value of 0.623. In the case of dyes bearing the COOH group, colorless lactone is the predominant tautomer of the molecular form H2R. A new classification of fluoresceins is developed. The dyes were divided into four groups based on the nature of tautomerism of the anions. In the case of the fluorescein type, the monoanions HR− exist predominantly as “carboxylate” tautomers, with ionized carboxylic and non–ionized hydroxylic group. For the dyes of the eosin type, the situation is opposite, while for the intervening type of compounds, the concentrations of the two tautomers are comparable. Dyes capable of forming lactone anions HR− were classified as the fourth type. For some of them, even the dianion R2− exists as a lactone. The relationship between the stepwise ionization constants, Ka1/Ka2, varies from 1.3 to 1.07 × 105 and is determined by the state of tautomeric equilibrium of molecules and ions.

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The difference between the aggregates of short-tailed and long-tailed cationic calix[4]arene in water as detected using fluorescein dyes

Cited by 13 publications

References 28 publications

Revisiting Fluorescent Calixarenes: From Molecular Sensors to Smart Materials

Revisiting Fluorescent Calixarenes: From Molecular Sensors to Smart Materials

Synthesis and Characterization of Chitosan‐Based Polyelectrolyte Complexes Doped with Xanthene Dyes

Protolytic Equilibria in Organized Solutions: Ionization and Tautomerism of Fluorescein Dyes and Related Indicators in Cetyltrimethylammonium Chloride Micellar Solutions at High Ionic Strength of the Bulk Phase

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