Indole based push-pull dyes bearing azo and dimethine: Synthesis, spectroscopic, NLO, anion affinity properties and thermal characterization

Keles E., Yahya M., Aktan E., Aydıner B., Seferoğlu N., Barsella A., ...More

JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, vol.402, 2020 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 402
  • Publication Date: 2020
  • Doi Number: 10.1016/j.jphotochem.2020.112818
  • Journal Name: JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Agricultural & Environmental Science Database, BIOSIS, Chemical Abstracts Core, Chimica, INSPEC
  • Keywords: Indole based chemosensor, Selective cyanide detection, Azo, Dimethine, NLO, DFT, TD-DFT, AQUEOUS-SOLUTION SYNTHESIS, SELECTIVE DETECTION, SENSING ABILITY, CYANIDE ANIONS, FLUORIDE, CHEMOSENSOR, COMPLEXES, MOLECULES, CHROMOPHORES, RECEPTORS
  • Gazi University Affiliated: Yes

Abstract

A series of novel indole based push-pull dyes bearing azo and dimethine chromophores in same structure were synthesized and characterized by Fourier Transform Infrared (FT-IR), H-1/C-13 nuclear magnetic resonance (NMR), and mass spectrometry. The photophysical properties of the dyes were determined in three solvents in UV-vis and theoretical studies. Their chemosensor and nonlinear optic (NLO) properties were also investigated. Anion selectivity and sensitivities of dyes were studied with some selected anions in ACN and interaction mechanisms were confirmed by spectrophotometric and H-1 NMR titration techniques. While the dyes showed affinity to F-, AcO-, CN-, and H2PO4- in the organic solvents such as DMSO and ACN and they showed selective behaviour only to CN- in partial aqueous solution. The thermal stabilities obtaining with thermogravimetric analysis (TGA) showed that the dyes have a good thermal stability up to around 300 degrees C.