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Journal of Fluorescence

, Volume 27, Issue 5, pp 1909–1922 | Cite as

Study on Photophysical Properties of N-Arylphthalamic Acid Derivative Containing 1, 2, 4-Triazole Scaffold

  • K. B. Akshaya
  • Anitha VargheseEmail author
  • Y. N. Sudhakar
  • Prajwal Lourdes Lobo
  • Louis George
ORIGINAL ARTICLE

Abstract

A novel N-arylphthalamic acid derivative, 2-({4-[(1H-1,2,4-triazol-1-yl)methyl]phenyl}carbamoyl)benzoic acid (TMPCB) was synthesized and their absorption and emission spectra were recorded in fifteen different solvents of varying polarities at room temperature. Ground state dipole moment of the derivative was calculated experimentally by Guggenheim method and solvatochromic approach proposed by Bilot-Kawski. The singlet excited state dipole moment of TMPCB were calculated experimentally based on different approaches of solvent polarity function proposed by Lippert–Mataga, Bakhshiev, Kawskii-Chamma-Viallet, Reichardt and Bilot-Kawski. Singlet excited state dipole moment was greater than ground state dipole moment in all the approaches which could be attributed to considerable π- electron density redistribution. Multiple Linear Regression (MLR) analysis based on Kamlet-Abboud-Taft and Catalan parameters were also studied to correlate solvatochromism and influence of solvents with absorbance and emission spectra. Ground and singlet excited state optimizations of the molecule were also performed using Gaussian 09 W software. HOMO-LUMO energies of the phthalamic acid derivative have been obtained using TD-DFT/PCM (B3LYP/6-31G (d, p)) computations and experimentally by using cyclic voltammetry. Mulliken charges and molecular electrostatic potential plot have also been generated from DFT calculations to identify nucleophilic and electrophilic sites of TMPCB.

Keywords

Guggenheim method Solvatochromic approach Phthalamic acid Dipole moment 

Notes

Acknowledgements

The authors are grateful to IISc, Bengaluru for computational analysis and would like to thank CUSAT-SAIF, Cochin University, Kochi for IR, 1H NMR, 13C NMR characterization and elemental analysis.

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Copyright information

© Springer Science+Business Media, LLC 2017

Authors and Affiliations

  • K. B. Akshaya
    • 1
  • Anitha Varghese
    • 1
    Email author
  • Y. N. Sudhakar
    • 1
  • Prajwal Lourdes Lobo
    • 2
  • Louis George
    • 1
  1. 1.Department of ChemistryChrist UniversityBengaluruIndia
  2. 2.Department of ChemistryMaharani’s Science College for WomenBengaluruIndia

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