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Synthesis and Fluorescence Properties of Novel indol-3yl-thiazolo[3,2-a][1,3,5]triazines and indole-3-carbaldehyde Schiff Bases

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Abstract

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 (Φf = 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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Acknowledgments

T V Sravanthi thanks Vellore Institute of Technology, Vellore, Tamilnadu, India, for providing Research Associateship and Dr. A Sivakumar, Professor, VIT University, Vellore for cyclic voltammetry analysis. The DST-FIST NMR facility, VIT-TBI for FT-IR and UV–Vis spectral characterization at VIT University are greatly acknowledged.

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  1. Organic Chemistry Division, School of Advanced Sciences, VIT University, Vellore, 632014, Tamilnadu, India

    T. V. Sravanthi & S. L. Manju

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  1. T. V. Sravanthi
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  2. S. L. Manju
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Correspondence to S. L. Manju.

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Sravanthi, T.V., Manju, S.L. Synthesis and Fluorescence Properties of Novel indol-3yl-thiazolo[3,2-a][1,3,5]triazines and indole-3-carbaldehyde Schiff Bases. J Fluoresc 25, 1727–1738 (2015). https://doi.org/10.1007/s10895-015-1659-1

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  • DOI: https://doi.org/10.1007/s10895-015-1659-1

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