Journal
JOURNAL OF FLUORESCENCE
Volume 25, Issue 6, Pages 1727-1738Publisher
SPRINGER/PLENUM PUBLISHERS
DOI: 10.1007/s10895-015-1659-1
Keywords
Indole-3-carbaldehyde Schiff bases; Indol-3-yl-thiazolo-s-trazines; Fluorescence spectroscopy; Physiochemical parameters; Antioxidant property; Cyclic voltammetry
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Novel photoactive 4-(4-chlorophenyl)-2-(1H-indol-3-yl)-6-substituted phenyl-2H-thiazolo[3,2-a][1,3,5]triazines were synthesized by the conjugate addition of ammonia to the indole-3-carbaldehyde Schiff bases followed by the condensation with 4-chlorobenzaldehyde. All the synthesized compounds were characterized by FT-IR, NMR, mass spectra and elemental analyses. Their antioxidant property, electrochemical and photophysical properties in different organic solvents were investigated. Comparative discussion on the photophysical properties of indole-3-carbaldehyde Schiff bases and 4-(4-chlorophenyl)-2-(1H-indol-3-yl)-6-substituted phenyl-2H-thiazolo[3,2-a][1,3,5]triazines has been described. The fluorescence quantum yield of Schiff bases (I broken vertical bar(f) = 0.66-0.70 in DMSO) found to be interestingly higher. High fluorescence quantum yield, large molar extinction coefficient, high stokes shift and smaller optical band gap positioning these new derivatives as an efficient metal free organic fluorescent and semiconductor material.
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