Changes in the reactivity of the fluorescent reagents carbazole-9-carbonyl chloride and 9-carbazolylacetic acid in the presence of cyclodextrins

Olives, Ana I.; Romero-Ale, Emiliano E.; Martín, M. Antonia; Castillo, B. del; López‐Alvarado, Pilar; Menéndez, J. Carlos

doi:10.1007/s10847-006-9248-1

Cited by 4 publications

(3 citation statements)

References 19 publications

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“…46 This value (pK a B 8) was assigned to the dissociation of the N(9)H group. This is significantly lower than the corresponding value for the dissociation of 6-mercaptopurine in the bulk (pK (2) a B 11). The discrepancy was attributed by the authors to the inability of the surfaceattached molecule to tautomerise to the alternative thione-type structure.…”

Section: Interface Effectmentioning

confidence: 58%

“…Mene´ndez and co-workers studied hydrolysis of carbazolecarbonyl chloride in the presence of cyclodextrins (CDs). 2 The rate of hydrolysis was enhanced presumably due to the complexation of the CDs with the carbazole moiety. Interestingly, carbazolylacetic acid loses the acetate group in the presence of hydroxypropylated cyclodextrin.…”

Section: Proximity Effect a Reactions Between Adjacent Groups In The ...mentioning

confidence: 99%

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Reactivity in organised assemblies

Chechik

2008

Annu. Rep. Prog. Chem., Sect. B: Org. Chem.

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Section: Interface Effectmentioning

confidence: 58%

Section: Proximity Effect a Reactions Between Adjacent Groups In The ...mentioning

confidence: 99%

Reactivity in organised assemblies

Chechik

2008

Annu. Rep. Prog. Chem., Sect. B: Org. Chem.

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“…Previous efforts have indicated that various forms of CD are effective in forming inclusion complexes with molecules that incorporate the 1,3,4-oxadiazole ring, [37][38][39] while carbazole-containing molecules have been the focus of a number of studies on the alteration of its luminance characteristics with inclusion in CDs. [40][41][42][43][44][45] The far right image in Fig. 1 presents the proposed arrangement of AO attached to a particle through a triazole.…”

Section: Resultsmentioning

confidence: 99%

Designing fluoroprobes through Förster resonance energy transfer: surface modification of nanoparticles through “click” chemistry

et al. 2010

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Fluorescence in Organized Assemblies

Memon¹,

Balouch²,

Hinze³

2008

Encyclopedia of Analytical Chemistry

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This article provides an overview of the general properties of organized assembly (ordered media) systems, such as aqueous surfactant and bile salt micelles, lipid (liposomes) and surfactant vesicles, and cyclodextrins (CDs), and summarizes their utilization to enhance the performance of analytical fluorescence measurements. In many instances, organic molecules and metal complex species when included within a CD cavity or solubilized and bound to surfactant aggregates exhibit enhanced fluorescence, improving detectability of such analytes. The altered microenvironment within the organized medium can impede the interfering action of other species (inorganic or organic) present in the sample matrix, which often improves the selectivity of the analytical method. These benefits of improved sensitivity and selectivity arise from the compartmentalization, isolation, and shielding of the excited singlet state of the guest analyte from quenching and nonradiative decay processes, as well as preventing side reactions that otherwise can occur in bulk solution (or sample matrix). Organic solvents or time‐consuming extraction steps can also be avoided, owing to the increased solubility of nonpolar organic or inorganic reagents and/or analyte molecules in water in the presence of the organized medium, allowing the use of an aqueous medium to perform the procedure. The possibility of conducting reactions and forming fluorescent organic or metal chelates in micellar (or other organized) media that are not observed in a bulk homogeneous solvent system serves to expand the scope of possible chemistries for design/development of new, unique, and improved fluorescent assays. Examples of fluorescent methods for determination of both organic and inorganic analytes are provided, which serve to illustrate the advantages and benefits accrued from the use of the micelles, vesicles, liposomes, or CDs in such procedures, along with experimental considerations and cautions in utilizing organized media.

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Changes in the reactivity of the fluorescent reagents carbazole-9-carbonyl chloride and 9-carbazolylacetic acid in the presence of cyclodextrins

Cited by 4 publications

References 19 publications

Reactivity in organised assemblies

Reactivity in organised assemblies

Designing fluoroprobes through Förster resonance energy transfer: surface modification of nanoparticles through “click” chemistry

Fluorescence in Organized Assemblies

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