Coumarin-indole conjugate donor-acceptor system: Synthesis, photophysical properties, anion sensing ability, theoretical and biological activity studies of two coumarin-indole based push-pull dyes


Aksungur T., AYDINER B. , SEFEROĞLU N. , ÖZKÜTÜK M., Arslan L., Reis Y., ...More

JOURNAL OF MOLECULAR STRUCTURE, vol.1147, pp.364-379, 2017 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 1147
  • Publication Date: 2017
  • Doi Number: 10.1016/j.molstruc.2017.06.079
  • Title of Journal : JOURNAL OF MOLECULAR STRUCTURE
  • Page Numbers: pp.364-379
  • Keywords: Coumarin-indole conjugate, Push-pull dye, Selective CN- detection, NLO, DFT, TD-DFT, Biological activity, FLUORIDE-SELECTIVE FLUORESCENT, ONE-POT SYNTHESIS, ANTIMICROBIAL EVALUATION, BIOACTIVE EVALUATION, RECOGNITION, CHEMOSENSOR, RECEPTORS, DESIGN, PROBE, RED

Abstract

Two coumarin-indole conjugate fluorescent dyes having donor-acceptor-donor (D-A-D) (CI-1 and CI-2) were synthesized, and characterized using IR, H-1/C-13 NMR and HRMS. The absorption and emission properties of the dyes were determined in different solvents. The anion sensitivity and selectivity of the dyes were studied with some anions (CN-, F-, AcO-, Cl-, Br-, I-, HSO4- and H2PO4-) in DMSO, and their interaction mechanisms were evaluated by spectrophotometric and H-1 NMR titration techniques. In addition, the molecular and electronic structures of CI-1, as well as the molecular complexes of CI-1, formed with the anions (F- and AcO-), were obtained theoretically and confirmed by DFT and TD-DFT calculations. CI-1 behaves as a colorimetric chemosensor for selective and sensitive detection of CN- in DMSO/H2O (9:1) over other competing anions such as F- and AcO-. However, only CN- interacts with chromophore CI-2 via Michael addition and the main absorption maxima shifts hypsochromically with an observed distinctive color change from orange to yellow. For using as a optic dye, the thermal stability properties of the dye's was determined by TGA (Thermal Gravimetric Analysis). Antimicrobial, antifungal and DNA-ligand interaction studies of the dyes were also examined. The dyes cause conformational changes on DNA and selectively bind to nucleotides of A/A and G/G. (C) 2017 Elsevier B.V. All rights reserved.