Potential fluorescent chemosensor based on L-tryptophan derivative: DFT based ESIPT process

Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy
Jayaraman JayabharathiKarunamoorthy Jayamoorthy

Abstract

The spectroscopic properties of (E)-2-(2-hydroxybenzylideneamino)-3-(1H-indol-3-yl) propanoic acid (HBDIPPA) has been studied in a series of different solvents. An excited state intramolecular proton transfer (ESIPT) process in hydroxy Schiff base has been studied using emission spectroscopy. DFT calculations on energy, HOMO-LUMO energies, MEP, dipole moment, charge distribution of the Schiff base derivative have been performed and discussed. The energy barrier for the interconversion of two rotamers is too high in the excited state than the ground state is shown by PES calculation. Positive values of laplacian ▿(2)ρ((rc)) (2.81) and electron density ρ((rc)) (0.22) are indicative of hydrogen bonds interactions. Absorption as well as fluorescence wavenumbers are correlated with Marcus and Reichardt-Dimroth solvent functions and also with Taft and Catalan solvent parameters. Schiff base HBDIPPA can be used as a new fluorescent sensor.

References

Mar 15, 2011·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·Jayaraman JayabharathiMarimuthu Venkatesh Perumal
May 17, 2011·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·Jayaraman JayabharathiMarimuthu Venkatesh Perumal
Sep 10, 2011·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·Jayaraman JayabharathiNatesan Srinivasan
Jan 20, 2012·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·Jayaraman JayabharathiKarunamoorthy Jayamoorthy

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Citations

Jan 9, 2014·Journal of Fluorescence·J JayabharathiK Jayamoorthy
Jan 15, 2013·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·J JayabharathiN Srinivasan
Oct 27, 2012·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·J JayabharathiV Thanikachalam
Oct 26, 2013·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·Kuo-xi XuChen-juan Wang
Dec 3, 2013·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·J JayabharathiA Arunpandiyan
Jul 5, 2013·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·J JayabharathiK Jayamoorthy
Jun 20, 2014·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·J JayabharathiA Arunpandiyan
Apr 5, 2018·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Hisato MatsumotoTatsuo Arai

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