9-Anthracenecarboxamide fluorescent probes for selective discrimination of picric acid from mono- and di-nitrophenols in ethanol. Issue 51 (23rd December 2015)

• Record Type: Journal Article
• Authors: Pandith, Anup; Kumar, Ashwani; Lee, Ju-Young; Kim, Hong-Seok
• Is Part Of: Tetrahedron letters. Volume 56:Issue 51(2015)
• Page Start: 7094
• Page End: 7099
• Publication Date: 2015-12-23
• Subjects: 9-Anthracenecarboxamide -- Picric acid -- Multiple hydrogen bonding -- Energy transfer -- Switch-off; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.11.017
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Significantly high change in relative fluorescence quenching of probe1 as compared to2 and3 with PA clearly showed the vitality of imidazole ring in1 for discrimination of PA among the mono- and di-nitrophenol derivatives. Highlights: A highly picric acid selective probe1 was designed and synthesized. The probe discriminated picric acid from mono- and di-nitrophenols in ethanol. LOD for PA is 1 μM in ethanol. PA was detected through hydrogen bonding and π – π interactions between probe1 and PA. Abstract: A new class of ' switch off ' anthracenecarboxamide-based sensing probes (1 –3 ) for the detection of picric acid (PA) was designed and synthesized. Probe1 exhibited the highest sensitivity and selectivity toward PA, enabling complete fluorescence quenching and exhibiting a high association constant (4.14 × 10 5 M −1 ) with a 1:1 stoichiometric ratio of1 to PA in EtOH. Probe1 was able to detect PA through multiple synergic interactions such as hydrogen bonding, π – π interactions between the electron-rich aromatic rings of anthracene and the electron-deficient aromatic ring of PA that resulted in a favorable fluorescence resonance energy transfer from the latter to the former. The ability of probe1 to sense PA was investigated by UV–visible, fluorescence, and 1 H NMR spectroscopies, as well as DFT calculations.