Microwave-enhanced and conventional procedures for the synthesis of coumarin-thiophene amides, sulfonamide, and urea derivatives: Synthesis, photophysical activities, and multiple anions signalling via different mechanisms

Yahaya I., Keles E., Putra A. U., Yahya M., Seferoğlu N., Seferoğlu Z.

JOURNAL OF MOLECULAR STRUCTURE, cilt.1204, 2020 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 1204
  • Basım Tarihi: 2020
  • Doi Numarası: 10.1016/j.molstruc.2019.127465
  • Dergi Adı: JOURNAL OF MOLECULAR STRUCTURE
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chimica, Compendex, INSPEC
  • Anahtar Kelimeler: Microwave-enhanced and conventional, procedures, Amide, Sulfonamide, Urea, Anion sensing, DFT, TEMPERATURE-CONTROLLED TAUTOMERISM, COLORIMETRIC CHEMOSENSORS, FLUORIDE ANION, PART 2, X-RAY, BINDING, RECOGNITION, EFFICIENT, NMR, INHIBITORS
  • Gazi Üniversitesi Adresli: Evet

Özet

Herein, two synthetic protocols (i.e. conventional and microwave-enhanced irradiation) have been designed and employed successfully for the synthesis of five chemosensors 3a-e. All the prepared compounds were obtained in excellent yields (90-98%). The anion interaction mechanisms, the effect of substitution on the absorption spectra, and the spectral characteristics of the prepared chemosensors (three amides, a disulfonamide, and a urea) have been investigated. The novel coumarin-thiophene appended dyes offer peculiar features in their ability to signal different anions under different types of mechanisms in the varying spectral range. These mechanisms were investigated and then confirmed using DFT and H-1 NMR. The optical properties of the novel chemosensors for anions were found to base on H-bonding, deprotonation, and nucleophilic attack and these were assessed and confirmed using H-1 NMR titration analysis. Again, theoretical calculations have employed to support the experimental results. All the probes have been found to be thermostable and applicable as optical dyes. (C) 2019 Elsevier B.V. All rights reserved.