Ratiometric fluorescence signalling of fluoride ions by an amidophthalimide derivative

Abstract

Fluorescence behaviour of 4-benzoylamido-N-methylphthalimide (1), designed and developed for selective detection of fluoride ions, is reported. 1 displays F --induced colour change that allows its detection with the naked eye. The F -specificity of the sensor system is evident from the fact that unlike F -, other halides do not affect the absorption characteristics of 1. Apart from the colorimetric response, the fluorescence output of 1 is also modulated by F -in a manner that permits ratiometric fluorescence signalling of F -as well. It is found that the system can detect F -in the concentration range of 10-60 μM. The results of the experiments and theoretical calculations unambiguously suggest that the changes of the electronic absorption and fluorescence behaviour of 1, which have been exploited for signalling purpose, are due to F --induced deprotonation of the 4-amido moiety of the sensor system.

Fluoride recognition by a chiral urea receptor linked to a phthalimide chromophore

“…Although bondelongation was observed in both cases (+0.013 A ˚for N-H 1 and +0.025 A ˚for N-H 2 ), it appeared that it was not sufficient for hydrogen abstraction by F -, in contrast to previous observations. 15 The H-F distances were also estimated and found to be 1. 710 A (H 1 -F) and 1.602 A ˚(H 2 -F) which were close to that experimentally found in the literature for complexation of isophthalimide-like compounds with fluoride ions.…”

“…Recently, Fabbrizzi and coworkers 14 have used urea/thiourea-phthalimide derivatives as chemosensors, where binding tendencies of the sensor towards anions were investigated by UV-Vis and 1 H-NMR titration. More recently, Samanta and coworkers 15 have studied the behavior of an amido-phthalimide derivative in the absence/presence of halide ions, suggesting F --induced deprotonation of the amido moiety of the sensor system as a signaling mechanism. However, one could also expect that a urea as an anion receptor may establish a H-bond interaction and form a stable complex instead of deprotonation (due to weak acidity of its N-H protons).…”

A New Isoindoline Based Schiff Base Derivative as Cu(II) Chemosensor: Synthesis, Photophysical, DNA Binding and Molecular Docking Studies

“…Recently, 4-benzoylamido-N-methylphthalimide and urea activated phthalimide chemosensor has been designed and developed for selective detection of fluoride ions ( Fig. 1) [19,20]. Based on the above considerations, in this article we report a novel chemosensor sensitive to solvent polarity, pH and selective to Cu 2+ ions.…”

Fluorescence Response of a 4-Trifluoroacetylaminophthalimide to Iodide Ions upon 254 nm Irradiation in MeCN

“…During our fluorescence studies of aminonaphthalimides, we have found that the trifluoroacetylation of the amino group markedly modifies the fluorescence properties of the naphthalimide derivatives by proton dissociation equilibrium of the amide part . Therefore, it is also expected that the trifluoroacetylation of amino-substituted aromatic carbonyl compounds, e.g., aminophthalimide, which displays an intramolecular charge-transfer (ICT) fluorescence, enhances the acidity of the amide proton and, as a result, effectively modulates the ICT fluorescence character through proton dissociation (Scheme ). , …”