New styryl based organic chromophores including free amino and azomethine groups: Syntheses, photophysical, NLO and thermal properties  

  1. Anka Utama Putra,
  2. Deniz Çakmaz,
  3. Nurgül Seferoğlu,
  4. Alberto Barsella and
  5. Zeynel SeferoğluORCID Logo

Submitting author affiliation: Gazi University, Ankara, Turkey

Beilstein Arch. 2020, 202030. doi:10.3762/bxiv.2020.30.v1

Published 23 Mar 2020

  • Preprint


In this manuscript, we have successfully synthesized and characterized a new series of styryl based push-pull dyes containing free amino group and their Schiff bases derivatives in which dicyanomethylene was used as the acceptor group and different para-substituted alkylamines as the donor groups and 2-pyridyl as proton sensitive group. All compounds showed absorption in the visible region and green-red emission with low quantum yields. The photophysical properties were examined in various solvents with different polarities. The absorption and emission maxima were shifted bathocromically by increasing solvents polarity however, there was no regular correlation with polarity parameter. Significant red shifts were observed in the absorption and fluorescence emission maxima on increasing the electron-donating ability of the substituents. The observed color changes were photographed naked eyes and under illuminating UV-lamp. The pH sensitive properties of newly prepared Schiff bases against TBAOH were examined inside DMSO, furthermore their reserve protonation were also investigated using TFA. The structural and electronic properties of all newly synthesized compounds were studied using DFT calculation. In addition, NLO property of compounds were investigated by DFT. For determination thermal properties of all compounds were investigated and they showed good thermal stability up to 250 oC by TGA analyses under inert atmosphere. Our results indicate that the styryl based new push-pull dyes are promising candidate materials for NLO and pH applications.

Keywords: Styryl dyes; Schiff base; Solvent effect; pH sensitive dyes; NLO; DFT 

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Putra, A. U.; Çakmaz, D.; Seferoğlu, N.; Barsella, A.; Seferoğlu, Z. Beilstein Arch. 2020, 202030. doi:10.3762/bxiv.2020.30.v1

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