A novel and synthetically facile coumarin-thiophene-derived Schiff base for selective fluorescent detection of cyanide anions in aqueous solution: Synthesis, anion interactions, theoretical study and DNA-binding properties

Chemchem M., Yahaya I., AYDINER B. , SEFEROĞLU N. , Doluca O., Merabet N., ...More

TETRAHEDRON, vol.74, no.48, pp.6897-6906, 2018 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 74 Issue: 48
  • Publication Date: 2018
  • Doi Number: 10.1016/j.tet.2018.10.008
  • Title of Journal : TETRAHEDRON
  • Page Numbers: pp.6897-6906
  • Keywords: Coumarin-thiophene, Schiff base, Cyanide detection In real sample, Fluorescence turn-on probe, ICT, DNA interaction, DFT, TD-DFT calculations, ON-A-MOLECULE, FLUORIDE-ION, COLORIMETRIC CHEMOSENSORS, SENSITIVE CHEMOSENSOR, CN-ION, SENSOR, RECOGNITION, RECEPTOR, PROBES, ZINC


A colorimetric and fluorescent chemosensor (chemosensor 2) for the detection of cyanide anions in aqueous solution has been designed and synthesized in high yield. The sensing mechanism of the chemosensor was verified via UV-vis, fluorimetric, and NMR titrations, and was theoretically explained using DFT and TD-DFT calculations. The chemosensor could optically discriminate the presence of fluoride ions over other anions by a color change from yellow to red with an enhancement of pink fluorescence in DMSO. However, it showed strong green fluorescence when CN- was added to a mixture of DMSO/water (6:4 v/v). Thus, the chemosensor can be employed in selective detecting of CN- besides other interference anions (F-, AcO(- )and H2PO4-) in aqueous solution. Moreover, 2 can be used to detect CN(- )at a concentration as low as 0.32 mu M, which is lower than the WHO guideline (2.7 mu M) for cyanide. A low quantity of CN- (1.08 mu M) can be detected and quantified using the prepared chemosensor. Moreover, the UV-vis and fluorescence spectroscopy studies of the interactions between 2 and dublex DNA revealed intercalative binding of calf thymus DNA to the chemosensor. (C) 2018 Elsevier Ltd. All rights reserved.