Sulfonamide carbazole receptors for anion recognition

Sulfonamide carbazole receptors for anion recognition

Carbazole-based receptors functionalized with two sulfonamide groups have been synthesized and their properties as anion receptors have been evaluated. The receptor with bis(trifluoromethyl)aniline groups has shown a very high affinity for halide ions, especially remarkable as only two hydrogen bond...

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Bibliographic Details
Published in:Organic & biomolecular chemistry Vol. 9; no. 24; p. 8321
Main Authors: Fuentes de Arriba, Ángel L, Turiel, María G, Simón, Luis, Sanz, Francisca, Boyero, Juan F, Muñiz, Francisco M, Morán, Joaquín R, Alcázar, Victoria
Format: Journal Article
Language:English
Published: England 21-12-2011
Subjects:
Anions - chemical synthesis
Anions - chemistry
Carbazoles - chemical synthesis
Carbazoles - chemistry
Crystallography, X-Ray
Fluorescence
Magnetic Resonance Spectroscopy
Models, Molecular
Molecular Structure
Stereoisomerism
Sulfonamides - chemistry
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Summary:Carbazole-based receptors functionalized with two sulfonamide groups have been synthesized and their properties as anion receptors have been evaluated. The receptor with bis(trifluoromethyl)aniline groups has shown a very high affinity for halide ions, especially remarkable as only two hydrogen bonds are formed in the complexes. (1)H NMR and fluorescence titrations have been carried out and binding constants up to 7.9 × 10(6) M(-1) have been reached. X-ray structures have been obtained and a modelling study has shown the possible reasons for the large affinity of these compounds for halide anions.
ISSN:1477-0539
DOI:10.1039/c1ob06126g