A novel carbazole-benzothiazole-based chemodosimeter for the chromogenic and fluorogenic recognition of CN

• Published in: New journal of chemistry Vol. 47; no. 24; pp. 11557 - 11564
• Main Authors: Maji, Atanu, Biswas, Amitav, Das, Akash, Gharami, Saswati, Aich, Krishnendu, Mondal, Tapan K
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 19.06.2023; Royal Society of Chemistry
• Subjects: Carbazoles; Charge transfer; Chemistry; Chemistry, Multidisciplinary; Cyanide process; Fluorescence; NMR; Nuclear magnetic resonance; Physical Sciences; Science & Technology; NAKED-EYE; CHEMOSENSOR; AGGREGATION-INDUCED EMISSION; SENSOR; PLANTS; IONS; SENSITIVE DETECTION; BINDING; FLUORESCENT-PROBE; CYANIDE DETECTION
• ISSN: 1144-0546; 1369-9261
• DOI: 10.1039/d3nj01157g

A novel colorimetric and fluorescent sensing probe, ( E )-3-(4-(9H-carbazol-9-yl)phenyl)-2-(benzo[ d ]thiazol-2-yl)acrylonitrile (CBTA), was synthesized and characterized by spectroscopic techniques. CBTA displayed "turn off" fluorescence in the presence of cyanide with a higher selectivity than that of others anions such as Br − , Cl − , I − , NO 3 − , SO 4 2− , SCN − , CO 3 2− , N 3 − , OH − , HCO 3 − , H 2 PO 4 − , HPO 4 2− , F − , ACO − , and PO 4 3− in a DMSO : H 2 O medium (40 : 60, v/v, HEPES buffer, pH = 7.2). The "turn off" fluorescence response mechanism can be attributed to the intra-molecular charge transfer (ICT) process, which is blocked by the nucleophilic attack of cyanide ions at the cyano vinyl group of the probe. The LOD was found to be 3.57 × 10 −8 M. The interaction involved behind the sensing of cyanide was investigated by Job's plot analysis, 1 H-NMR, and mass spectroscopic studies. DFT and TDDFT were also employed to verify the experimental outcomes. Moreover, the test strip experiment provides a wide application prospect of the receptor for detecting poisonous cyanide in the environment and biological system. A novel colorimetric and fluorescent sensing probe, CBTA, was designed for the selective detection of CN − .