Add time:08/22/2019         Source:sciencedirect.com

The electronic absorption and fluorescence spectra of coumarin derivative, (S)-(1-((7-hydroxy-2-oxo-2H-chromen-4-yl)methyl)-1H-1,2,3-triazol-4-yl)methyl2-(((9H-fluoren-9-yl)methoxy)cabonylamino)-3-phenylpropanoate have been studied in solvents of different polarities, and the data were used to study the solvatochromic properties. The absorption maximum remains almost unchanged with the increase in solvent polarity, whereas a red shift in fluorescence emission maximum was observed. Synthesized compound (S)-(1-((7-hydroxy-2-oxo-2H-chromen-4-yl)methyl)-1H-1,2,3-triazol-4-yl)methyl2-(((9H-fluoren-9-yl)methoxy)cabonylamino)-3-phenylpropanoate was characterized by 1H and 13C NMR, and FT-IR spectral studies. The ground and excited state dipole moments of molecule were obtained from Bakshiev's and Bilot–Kawski's equations by means of solvatochromic shift method. High value of dipole moment is observed for excited state as compared to ground state value and this is attributed to more polar excited state of molecule. Also, fluorescence emission peak undergoes a bathochromic shift with increase in the polarity of the solvent, confirming π → π* transition. Numerical calculations are performed using B3LYP/6-31G(d) level of theory for the ground state using Gaussian 03. Studies in different solvents are also done using IEF-PCM method and UA0 radii. A comparative analysis between the values of dipole moment in gas phase and various solvents is also done for the ground state.

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