betadex and anthracene

A green synthesis method for nanoscale silver using β-cyclodextrin as both reducing agent and stabilizer was developed. β-cyclodextrin was used not only as a reducing agent but also a stabilizing agent for nano-silver, and is also an excellent detection substrate due to its special structure (inner hydrophobic and outer hydrophilic ring structure). Then, the green synthesized silver nanoparticles were used as Surface-enhanced Raman spectroscopy (SERS) enhanced substrates to detect polycyclic aromatic hydrocarbons, such as: anthracene, pyrene, chrysene and triphenylene. The SERS substrate can be used for both quantitative detection of the four polycyclic aromatic hydrocarbons and qualitative identification of mixtures of these hydrocarbons. This synthesis method is simple and convenient, having great potential in simultaneous and rapid detection of environmental organic pollutants.

Topics: Anthracenes; beta-Cyclodextrins; Chrysenes; Green Chemistry Technology; Hydrophobic and Hydrophilic Interactions; Metal Nanoparticles; Polycyclic Aromatic Hydrocarbons; Pyrenes; Silver; Spectrum Analysis, Raman

The negative health impact of polycyclic aromatic hydrocarbons (PAHs) and differences in pharmacological activity of enantiomers of chiral molecules in humans highlights the need for analysis of PAHs and their chiral analogue molecules in humans. Herein, the first use of cyclodextrin guest-host inclusion complexation, fluorescence spectrophotometry, and chemometric approach to PAH (anthracene) and chiral-PAH analogue derivatives (1-(9-anthryl)-2,2,2-triflouroethanol (TFE)) analyses are reported. The binding constants (K

Topics: Anthracenes; beta-Cyclodextrins; Calibration; Kinetics; Least-Squares Analysis; Multivariate Analysis; Polycyclic Aromatic Hydrocarbons; Regression Analysis; Spectrometry, Fluorescence; Thermodynamics

Multi-micelle aggregation (MMA) mechanism is widely acknowledged to explicate large spherical micelles self-assembly, but the process of MMA during self-assembly is hard to observe. Herein, a novel kind of strong, regular microspheres fabricated from self-assembly of amphiphilic anthracene-functionalized β-cyclodextrin (CD-AN) via Cu(I)-catalyzed azide-alkyne click reactions is reported. The obtained CD-AN amphiphiles can self-assemble in water from primary core-shell micelles to secondary aggregates with the diameter changing from several tens nm to around 600-700 nm via MMA process according to the images of scanning electron microscopy, transmission electron microscopy, and atomic force microscopy as well as the dynamic light scattering measurements, followed by further crosslinking through photo-dimerization of anthracene. What merits special attention is that such photo-crosslinked self-assemblies are able to disaggregate reversibly into primary nanoparticles when changing the solution conditions, which is benefited from the designed regular structure of CD-AN and the rigid ranging of anthracene during assembly, thus confirming the process of MMA.

Topics: Anthracenes; beta-Cyclodextrins; Micelles; Molecular Structure; Particle Size; Surface Properties; Surface-Active Agents

A modified cyclodextrin is synthesized as an anthracene derivative of 6-deoxy- 6-aminoethylamino-β-cyclodextrin and characterized using IR, NMR, and mass spectral techniques. The compound acts as a sensor of Pb(2+) ions in a pool of several metal ions, by enhancement of fluorescence. The absorption spectrum does not show significant changes on the addition of metal ions. The stoichiometry and the binding constant of the complex are determined using fluorescence data. The enhancement of fluorescence is attributed to the aminoethyl and imino nitrogens of the spacer of anthracene and β-cyclodextrin. The compound is quite stable under the testing conditions and the sensing is attributed to the charge transfer mechanism.

Topics: Anthracenes; beta-Cyclodextrins; Biosensing Techniques; Fluorescence; Fluorescent Dyes; Lead; Magnetic Resonance Spectroscopy; Spectrometry, Fluorescence

A new fluorescent β-cyclodextrin has been synthesized by coupling an anthracene moiety to the cyclic oligosaccharide via click chemistry. The influence of the triazole spacer was compared to the simple amino and amido linkers. While a sensing ability toward adamantan-1-ol was observed with the latter two spacers, the absence of inclusion capacity prevents the triazole modified cyclodextrin from showing any fluorescence variations. The difference in the binding behaviors studied by Isothermal Titration Calorimetry, UV-vis and fluorescence spectroscopies, was highlighted by the NOESY NMR spectra of the modified cyclodextrins: whereas a free cavity was observed for the amino and amido linkers, an important obstruction was obtained in the case of the triazole.

Topics: Anthracenes; beta-Cyclodextrins; Magnetic Resonance Spectroscopy; Molecular Structure; Spectrometry, Fluorescence; Triazoles

Two highly water-soluble amino acids, which derived from beta-CDs, i.e., glutamic acid-beta-cyclodextrin (GluCD) and ethylene-diamine-beta-cyclodextrin (EDCD), were synthesized and were examined for their effect on solubilization of anthracene (ANT), complexation of cadmium (Cd2+), and elution removal of ANT and Cd2+ in soil. The results showed that GluCD and EDCD were powerful complexant for ANT and Cd2+. In the presence of 10 g/L GluCD and EDCD, the solubilization of ANT increased by 47.04 and 23.85 times compared to the control, respectively. GluCD resulted in approximately 90% complexation of Cd2+ while 70% complexation was observed for EDCD. Simultaneously, GluCD and EDCD could greatly enhance the elution removal of ANT and Cd2+ from soil. GluCD resulted in the highest elution efficiency of ANT and Cd2+. With the addition of 10 g/L GluCD, 53.5% of ANT and 85.6% of Cd2+ were eluted, respectively. The ANT had a negligible effect on the Cd2+ removal due to different complexing sites of ANT and Cd2+, while Cd2+ enhanced the ANT removal under the addition of GluCD because Cd2+ neutralized the -COOH group of GluCD. Adversely, the removal of ANT was decreased with Cd2+ under the addition of EDCD, this was due to the fact that Cd2+ enhanced the polarity of EDCD molecule and inhibited the complexation between ANT and EDCD. The study suggested that GluCD could be preferred and be successfully applied to remediation of heavy metals or organic compounds in contaminated soil.

Topics: Anthracenes; beta-Cyclodextrins; Cadmium; Ethylenediamines; Glutamic Acid; Soil Pollutants