Synthesis and detailed spectroscopic characterization of various hydroxy-functionalized fluorescent chalcones: A combined experimental and theoretical study

M. Jagadeesh, M. Lavanya, B. Hari Babu, Kiryong Hong, Rory Ma, Joonghan Kim, Tae Kyu Kim

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Abstract Four different bright yellow to orange hydroxy-substituted chalcones (i.e., 2′,4-di-hydroxy (1), 2′,3′,4-trihydroxy (2), 2′,3′,4′-trihydroxy (3), and 2′-hydroxy-4-methoxy (4) chalcones) were synthesized and characterized by LC-MS, FT-IR, FT-Raman, and fluorescence spectroscopy and thermogravimetric analysis. UV-visible absorption spectroscopy was also used. The experimental (theoretical) bandgaps of 1, 2, 3, and 4 are 2.89 (2.90), 2.93 (2.95), 3.04 (3.09), and 3.01 (2.91) eV, respectively. The hydroxy-substituted chalcones exhibited strong dual emissions as a consequence of the locally excited states followed by internal charge transfer processes. The molecular structures, lowest energy transitions, vibrational frequencies, and spectroscopic information were calculated using density functional theory and time-dependent density functional theory methods at the B3LYP/6-31G(d,p) theoretical level. The experimental and theoretical data were compared and the relationship between them was briefly discussed.

Original languageEnglish
Article number13753
Pages (from-to)557-564
Number of pages8
JournalSpectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy
Publication statusPublished - 2015 Jun 14


All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Atomic and Molecular Physics, and Optics
  • Instrumentation
  • Spectroscopy

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