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Synthesis, Structural, Thermal and Photo-Physical Properties of Triazine Based NLO Material

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Abstract

Three novel triazine based organic chromophores with D-π-A (Donor-π system- Acceptor) push-pull type have been synthesized from 2, 4-diamino-6-phenyl-1,3,5-triazine as a starting material. Structures of all the three compounds have been confirmed by UV-Visible absorption, FT-IR, NMR and Mass spectral techniques. Their photo physical and thermal properties have been investigated. Among the three compounds, 6-phenyl-2,4-((4-amino-1,5-dimethyl-2-phenyl pyrazol-3-ylidene)(4-nitro benzylidene))-diamino-1, 3, 5-triazine (NDP) showed positive solvatochromism compared to the other two compounds. The absorption in the UV region of these three compounds were found to be less dependent on solvent polarities, whereas the red shifted fluorescence was strongly dependent on solvent polarities. The TGA data indicates that all the three compounds are stable up to 160 °C. Measurement of non linear optical properties showed that there is an increased second harmonic generation (SHG) efficiency with respect to urea indicating the existence of high molecular nonlinearity in NDP.

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Acknowledgements

Authors thank the Management of Thiagarajar College, Madurai and one of the authors (PT) and thank the Defence Research and Development Organization (DRDO), New Delhi for financial support, SAIF, IIT Chennai, and CECRI, Karaikudi for providing analytical facilities.

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Authors and Affiliations

  1. Department of Chemistry, Thiagarajar College, Madurai, 625 009, India

    M. Shyamala Devi, P. Tharmaraj & R. Ebenezer

  2. Department of Chemistry, The American College, Madurai, 625 002, India

    C. D. Sheela

Authors
  1. M. Shyamala Devi
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  2. P. Tharmaraj
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  3. C. D. Sheela
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  4. R. Ebenezer
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Corresponding author

Correspondence to P. Tharmaraj.

Electronic supplementary material

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Fig. 1

1H Nmr spectrum of TDP (DOC 159 kb)

Fig. 2

13C Nmr spectrum of TDP (DOC 261 kb)

Fig. 3

Mass spectrum of TDP m/z = 466.17 (DOC 106 kb)

Fig. 4

1H Nmr spectrum of NDP (DOC 244 kb)

Fig. 5

13C Nmr spectrum of NDP (DOC 89 kb)

Fig. 6

Mass spectrum of NDP m/z = 505.2 (DOC 114 kb)

Fig. 7

1H Nmr spectrum of IDM (DOC 107 kb)

Fig. 8

13C Nmr spectrum of IDM (DOC 96 kb)

Fig. 9

Mass spectrum of IDM m/z = 430.19 (DOC 101 kb)

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Devi, M.S., Tharmaraj, P., Sheela, C.D. et al. Synthesis, Structural, Thermal and Photo-Physical Properties of Triazine Based NLO Material. J Fluoresc 23, 399–406 (2013). https://doi.org/10.1007/s10895-012-1154-x

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  • DOI: https://doi.org/10.1007/s10895-012-1154-x

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