Luminescent Mannich bases : Synthesis, crystal structures, and photophysical properties

Research output: Journal Publications and ReviewsRGC 21 - Publication in refereed journalpeer-review

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Author(s)

  • Andrei A. Patrascu
  • Cristina Tablet
  • Sorana Ionescu
  • Mihaela Hillebrand
  • Marius Andruh

Related Research Unit(s)

Detail(s)

Original languageEnglish
Article number140370
Journal / PublicationJournal of Molecular Structure
Volume1322
Issue numberPart 2
Online published13 Oct 2024
Publication statusPublished - 15 Feb 2025

Abstract

Three Mannich bases have been obtained starting from 5‑bromo-salicylaldehyde: 5‑bromo-3-(((2-(dimethylamino)ethyl)(methyl)amino)methyl)-2-hydroxybenzaldehyde (TMEN), 5‑bromo-3-((benzyl(methyl)amino)methyl)-2-hydroxybenzaldehyde (MBA), 5‑bromo-3-(ethyl(methyl)amino)methyl)-2-hydroxybenzaldehyde (EMA). The crystal structure of MBA has been solved. The UV–Vis absorption and emission spectra were investigated in different solvents, revealing the presence of several species, the neutral forms, the zwitterionic, the anionic and the cationic (the protonated nitrogen) ones. In order to characterize the last two species, further experiments were performed in the presence of hydrogen extracting and hydrogen donating compounds, sodium fluoride (NaF) and tetrabutylammonium hydroxide (TBOH) to evidence the anion, and trichloroacetic acid (TCA) for the protonated cation. The experimental results were rationalized by DFT calculations of the potential energy surfaces (PES) of the S0 and S1 states and of the absorption and emission maxima. © 2024 Elsevier B.V.

Research Area(s)

  • Crystal structures, DFT calculations, Mannich reaction, Salicylaldehyde

Citation Format(s)

Luminescent Mannich bases: Synthesis, crystal structures, and photophysical properties. / Patrascu, Andrei A.; Tablet, Cristina; Ionescu, Sorana et al.
In: Journal of Molecular Structure, Vol. 1322, No. Part 2, 140370, 15.02.2025.

Research output: Journal Publications and ReviewsRGC 21 - Publication in refereed journalpeer-review