A reaction-based carbazole-dicyanovinyl conjugated colorimetric and ratiometric fluorescent probe for selective detection of cyanide ions


Battal A., Kassa S. B., ALTINÖLÇEK GÜLTEKİN N., TAVASLI M., ONGANER Y.

SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, cilt.304, 2024 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 304
  • Basım Tarihi: 2024
  • Doi Numarası: 10.1016/j.saa.2023.123350
  • Dergi Adı: SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, BIOSIS, CAB Abstracts, Chemical Abstracts Core, Chimica, Compendex, INSPEC, MEDLINE, Veterinary Science Database
  • Anahtar Kelimeler: Carbazole, Colorimetric and ratiometric probe, CN-, Donor-pi-acceptor, Isoemissive point
  • Atatürk Üniversitesi Adresli: Evet

Özet

In the present work, 4-(9'-hexylcarbazol-3'-yl)benzylidenemalononitrile 5 (probe L) was tested as a colorimetric and ratiometric fluorescent probe in dimethyl sulfoxide (DMSO) medium towards anions, cations and neutral molecules. The sensing properties of probe L were investigated by using UV-Vis absorption and fluorescence spectroscopy techniques. Probe L showed selectivity and sensitivity towards cyanide ions (CN-) in the presence of analytes used. Upon the addition of CN-, intramolecular charge transfer (ICT) band at 425 nm in UV spectrum disappeared. In addition, ICT emission intensity at 593 nm decreased and ligand-centred (LC) emission intensity at 480 nm increased. These findings indicate that nucleophilic conjugate addition of CN- to the dicyanovinyl group of probe L successfully occurs, hence forming a new adduct between probe L and CN-. In this adduct, pi-conjugation was partially blocked, and the ICT transfer was hindered. Adduct formation was proved by Job's plot, H-1 NMR and FT-IR analysis. Probe L showed very low limit of detection (LOD) value of 1.467 nM towards CN-. Probe L was also applied to the CN- detection in real-world water samples by the spike and recovery method. The maximum relative standard deviation (RSD) value was 4.24, indicating this method works successfully. Therefore, probe L could find a potential use in detection of CN- in liquid media.