Systematic study of the fluorescent properties of cinnamaldehyde phenylhydrazone and its interactions with metals: Synthesis and photophysical evaluation

MARCO ANDRÉS MELLADO GARCÍA, Rafaela Sariego-Kluge, César González, Katy Díaz, Luis F. Aguilar, Manuel A. Bravo

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

Hydrazones are organic compounds with applications in various fields of research, including fluorescent applications. In this investigation, the compound cinnamaldehyde phenylhydrazone was synthesized by condensation between cinnamaldehyde (1) and phenylhydrazine (2). Furthermore, the photophysical properties were evaluated in the presence and absence of inorganic salts, and it was found that the fluorescence intensity selectively decays with CuCl2 in a thermodynamically spontaneous process (ΔG = negative). In addition, computational approaches were used, which identified the transfer of electrons from highest-occupied molecular orbital HOMO of compound 3 to the lowest unoccupied molecular orbital (LUMO) of CuCl2 as the key interaction for quenching the fluorescence intensity of cinnamaldehyde phenylhydrazone. Additionally, the potential application of compound 3 as a Cu2+ chemosensor in different water samples was evaluated. This compound was found to exhibit better recovery of Cu2+ in natural water samples (higher than 99.3%) than in drinking water (66%).

Original languageEnglish
Article number128430
JournalJournal of Molecular Structure
Volume1217
DOIs
StatePublished - 5 Oct 2020
Externally publishedYes

Keywords

  • Cinnamaldehyde phenylhydrazone
  • HOMO -LUMO electron transfer
  • Selective fluorescence quenching
  • Thermodynamic properties

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