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<p>A novel aminochalcone, (<i>E</i>)-1-(4-aminophenyl)-3-(1-benzyl-pyrrol-2-yl)prop-2-en-1-one, was synthesized via Claisen–Schmidt condensation and fully characterized using FT-IR, NMR spectroscopy, and GC-MS analysis. The compound’s photophysical properties were studied using UV–Vis absorption and fluorescence spectroscopy in solvents of varying polarity. These studies revealed marked solvatochromic and solvatofluorochromic behavior, which is consistent with an intramolecular charge-transfer process. In polar media, the compound exhibited strong bathochromic shifts and a solvent-dependent fluorescence quantum yield of 0.012 ± 0.001, 0.061 ± 0.004 and 0.098 ± 0.007 in methanol, acetonitrile and chloroform, respectively. Ground- and excited-state dipole moments calculated from Lippert–Mataga and Bakhshiev correlations confirmed an increase upon excitation. DFT calculations at the B3LYP/6-311G(d, p) level corroborated the experimental results, indicating a minimal HOMO-LUMO gap and a planar conjugated system exhibiting donor–acceptor properties. Furthermore, the compound effectively functioned as a fluorescent probe for protein labeling under mildly acidic conditions (pH = 4.0) via 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide-mediated coupling, yielding consistent emission across proteins of different molecular weights. Altogether, these results indicate that this new aminochalcone possesses structural tunability, stable fluorescence, and bioconjugation capability, positioning it as a promising scaffold for fluorescence-based biochemical applications.</p>

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Synthesis, Photophysical Characterization, and DFT Analysis of (E)-1-(4-aminophenyl)-3-(1-benzyl-pyrrol-2-yl) Prop-2-en-1-one, a Novel Aminochalcone that can be Used as a Fluorescent Probe for Protein Labeling

  • 期刊论文

  • 发表日期：

    2025年11月28日

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  • Pablo Martínez,
  • Adriana Flores,
  • Karen Bonilla,
  • Neudo Urdaneta,
  • Gustavo Benaím,
  • Nieves Canudas,
  • José Bubis

摘要

A novel aminochalcone, (E)-1-(4-aminophenyl)-3-(1-benzyl-pyrrol-2-yl)prop-2-en-1-one, was synthesized via Claisen–Schmidt condensation and fully characterized using FT-IR, NMR spectroscopy, and GC-MS analysis. The compound’s photophysical properties were studied using UV–Vis absorption and fluorescence spectroscopy in solvents of varying polarity. These studies revealed marked solvatochromic and solvatofluorochromic behavior, which is consistent with an intramolecular charge-transfer process. In polar media, the compound exhibited strong bathochromic shifts and a solvent-dependent fluorescence quantum yield of 0.012 ± 0.001, 0.061 ± 0.004 and 0.098 ± 0.007 in methanol, acetonitrile and chloroform, respectively. Ground- and excited-state dipole moments calculated from Lippert–Mataga and Bakhshiev correlations confirmed an increase upon excitation. DFT calculations at the B3LYP/6-311G(d, p) level corroborated the experimental results, indicating a minimal HOMO-LUMO gap and a planar conjugated system exhibiting donor–acceptor properties. Furthermore, the compound effectively functioned as a fluorescent probe for protein labeling under mildly acidic conditions (pH = 4.0) via 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide-mediated coupling, yielding consistent emission across proteins of different molecular weights. Altogether, these results indicate that this new aminochalcone possesses structural tunability, stable fluorescence, and bioconjugation capability, positioning it as a promising scaffold for fluorescence-based biochemical applications.