Cyclodextrin Combinations with Azocompounds

Luboch, Elżbieta; Poleska-Muchlado, Z.; Jamrógiewicz, Marzena; Biernat, Jan F.

doi:10.1007/1-4020-3687-6_13

Cited by 7 publications

(3 citation statements)

References 57 publications

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“…As shown in Figure S7, after 10 min of 400 W irradiation, most azo moieties completed the isomerization. α-CD can interact with trans -azobenzene to form a 1:1 inclusion complex but cannot include the cis -azobenzene to form an inclusion complex because of the mismatch between the host and guest. − Our investigation also confirmed that α-CD did not interact or interacted very weakly with cis -PBA. The absorption band at 430 nm due to the n−Π* transition of cis -PBA exhibits no significant spectral change upon addition of varying concentrations of α-CD (Figure S6).…”

Section: Results and Discussionsupporting

confidence: 63%

Photoreversible Polymer–Surfactant Micelles Using the Molecular Recognition of α-Cyclodextrin

et al. 2013

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Photoreversible micelles were achieved by a combination of commercially available components sodium alginate (Alg), tetradecyltrimethylammonium bromide (TTAB), α-cyclodextrin (α-CD), and 4-(phenylazo)benzoic acid (PBA). Under visible light irradiation, α-CD interacted more favorably with PBA than with alkyl chains of TTAB. Therefore, polymer-surfactant micelles were formed by the self-assembly of Alg and TTAB through electrostatic attraction. After UV irradiation, micelles were disrupted because PBA in the cis form lost its ability to complex with α-CD, and then the latter was interacted with TTAB to prevent the association of alkyl chains of TTAB. On alternating irradiation of this quaternary system with UV and visible light, this reversible micellization process can be recycled many times.

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Section: Results and Discussionsupporting

confidence: 63%

Photoreversible Polymer–Surfactant Micelles Using the Molecular Recognition of α-Cyclodextrin

et al. 2013

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“…found from the study using induced circular dichroism that β and γ CD form the 1:1 complexes with CR in water. 7,8) By using 1 H NMR spectrometry and 13 C NMR spectrometry, 9) it was confirmed that the benzene ring moiety of p nitrophenol or p nitrophenolate was included into the cavity of α CD, and it was reported that 1 Hs' chemical shifts of p nitrophenolate were observed with the addition of α CD and β CD. 10) NMR studies of aqueous solutions of γ CD and the azo dye CR show distinct, concentration independent 1 H NMR signals and that a very stable 1:1 pseudorotaxane is formed.…”

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confidence: 95%

“…10) NMR studies of aqueous solutions of γ CD and the azo dye CR show distinct, concentration independent 1 H NMR signals and that a very stable 1:1 pseudorotaxane is formed. 7,11) The spectra of CR in water solution with various sugars such as sucrose, lactose, cellobiose, maltose, trehalose, α and γ CD were measured by UV VIS spectrophotometer, and it was shown that the λmax of the spectra shifted with the addition of sugars at 500 nm or thereabout. 12) To obtain more useful information on how to stabilize amphiphilic compounds such as polyphenols and glycosides by addition of sugars, we carried out experiments on the interaction of CR with sugars such as the α CD, β CD and γ CD series including original, glucose and maltose branched CDs by changing pH and the concentration of the sugars, by using visible light and NMR spectrometry.…”

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confidence: 99%

Dospectral Analyses of Interaction between Congo Red and Cyclodextrins at Various pH

Kobayashi¹,

Miwa²,

Tanaka³

et al. 2008

J. Appl. Glycosci.

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In our previous paper, 1) we reported the comparative spectral analyses of 0.014 mM CR with 4% concentration of CDs. Beyond a certain concentration of CDs, the spectra of CR were not changed. Therefore, this time, we used 0.02 mM CR and various concentrations of CDs to obtain further information on the interaction of CR with CDs. Moreover, we found that absorption spectra of CR were changed by the addition of cyclodextrins at pH 5.0.As for spectrophotometry by visible light, it was demonstrated that methyl orange formed an inclusion complex with CDs in a dissolved state and various color changes were observed with the addition of CDs and ethanol. As for the complex formation of CR with CDs, there are several reports.5 9) It is reported that the raman optical activity (ROA) spectra of CR with γ cyclodextrin were measured at the concentration of 0.05 mM (CR) and 5 mM (γ CD), and that the ROA spectra may reflect the difference in the positions of the SO3 groups in the guest molecules.5) It is revealed that the phenomenon of induced optical activity denotes the induction of optical activity in the molecules of an achiral compound when it is in contact with the molecules of a chiral compound, and that the main consequence of this interaction is asymmetric perturbation of the electronic transitions of the chromophore by the field of the inducer to be exhibited in the optical rota- Abstract: The absorbance of 500 nm of various concentration of cyclodextrin (CD) containing 0.02 mM congo red (CR) solution were obtained. The absorbance was plotted toward the concentration of CDs to obtain curves showing the relation of the variation of the absorbance to the concentration of CDs. In the case of the α-CD series (α-CD, G1-α-CD and G2-α-CD), the absorbance increased in accordance with the CDs concentration, and the increasing ratio of G2-α-CD was considerably higher than those of α-and G1-α-CD. On the other hand, in the case of the β-CD and γ-CD series, the absorbance curves showed that they reached a plateau at a certain concentration. It was almost same among the β-CD series. A certain interaction, which was maximum at a ratio less than CR: β-CD 1:250, might occur between CR and β-CD, except inclusion complex formation. The absorbance curves for the γ-CD series showed that it reached a plateau at a considerably lower concentration than that of β-CD. The formation ratio of CR: γ-CD complex was calculated as 1:2 at pH 5.0. We inferred that cavity size and the character of CDs affected accessing style to CR molecules and that the CR molecule was unable to access α-CD because the cavity size was too small to incorporate a CR molecule. The cavity of β-CD may be able to attract a CR molecule, but is unable to incorporate it. The cavity of γ-CD may be able to incorporate a CR molecule. As a conclusion, the α-and β-CD series were able to interact with CR molecules except in inclusion complexes, whereas, the γ-CD series were able to form inclusion complexes. In the NMR spectroscopy of CR in CDs containing D2O, the 1 H NMR profile of...

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Photochemical Control of Reversible Encapsulation

2010

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Mithilfe von Licht und Wärme können Moleküle in einem chemischen System zwischen Kapseln und freier Lösung wechseln. Die Grundlage für diesen Prozess bildet die Isomerisierung von Azobenzol: Während das trans‐Isomer verkapselt werden kann, gelingt dies für das cis‐Isomer nicht (siehe Bild; C grau und braun, Br violett, O rot, N blau, H weiß). Auf photochemischem Weg kann auch zwischen unterschiedlichen Kapselaggregaten geschaltet werden.

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Cyclodextrin Combinations with Azocompounds

Cited by 7 publications

References 57 publications

Photoreversible Polymer–Surfactant Micelles Using the Molecular Recognition of α-Cyclodextrin

Photoreversible Polymer–Surfactant Micelles Using the Molecular Recognition of α-Cyclodextrin

Dospectral Analyses of Interaction between Congo Red and Cyclodextrins at Various pH

Photochemical Control of Reversible Encapsulation

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