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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9 Citations (Scopus)

Abstract

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
Volume150
DOIs
Publication statusPublished - 2015 Jun 14

Bibliographical note

Funding Information:
This work was financially supported by National Research Foundation of Korea (NRF) grants funded by the Korean government (MEST and MSIP) ( 2007-0056095 , 2012K2A1A2033072 , 2013S1A2A2035406 , and 2013R1A1A2009575 ).

Publisher Copyright:
© 2015 Elsevier B.V.

All Science Journal Classification (ASJC) codes

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

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