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Rational design of a macrocyclic-based chemosensor for anions
Kalpana R Dey1, Bryan M Wong, Md Alamgir Hossain
1Department of Chemistry and Biochemistry, Jackson State University, 1400 J. R. Lynch Street, P.O. Box 17910, Jackson, MS 39212, USA.
Tetrahedron Letters
|April 20, 2010
Summary
A novel macrocyclic fluorescence chemosensor selectively binds anions. This sensor shows high affinity for oxoanions, chloride, and iodide, with binding constants up to four orders of magnitude.
Area of Science:
- Supramolecular Chemistry
- Analytical Chemistry
- Chemical Sensing
Background:
- Development of selective chemosensors is crucial for detecting various anions.
- Macrocyclic compounds offer unique binding cavities for guest molecules.
- Fluorescence spectroscopy provides a sensitive platform for monitoring binding events.
Purpose of the Study:
- To design and synthesize a novel macrocyclic-based fluorescence chemosensor.
- To investigate the binding capabilities of the chemosensor towards a range of anions.
- To elucidate the binding interactions at a molecular level using computational methods.
Main Methods:
- Synthesis of a macrocyclic chemosensor from dansyl chloride and a hexaaminomacrocycle.
- Anion binding studies using fluorescence spectroscopy in DMSO.
- Computational analysis using ab initio calculations based on density functional theory (DFT).
Main Results:
- The synthesized macrocyclic compound acts as a fluorescence chemosensor for anions.
- The chemosensor exhibits 1:1 stoichiometry binding with high affinity for oxoanions, chloride, and iodide.
- Binding constants reached up to four orders of magnitude, indicating strong interactions.
- DFT calculations revealed ligand deformation and specific hydrogen bonding interactions (NH…X(-) and CH…X(-)) with anions, except fluoride.
Conclusions:
- A novel macrocyclic fluorescence chemosensor has been successfully synthesized and characterized.
- The chemosensor demonstrates high selectivity and affinity for specific anions, particularly oxoanions, chloride, and iodide.
- The study provides insights into the binding mechanism through experimental and computational approaches, paving the way for advanced anion sensing applications.
