Synthesis, characterization, photophysical and DFT studies of (E)-1-(4-aminophenyl)-3-(1-benzyl-pyrrol-2-yl) prop-2-en-1-one, a novel aminochalcone

Chalcones constitute a distinct family of compounds with intrinsic fluorescence properties that make them valuable tools for a variety of applications. In this work, a new chalcone core derivative, ( E )-1-(4-aminophenyl)-3-(1-benzyl-pyrrol-2-yl) prop-2-en-1-one, was synthesized via a Claisen–Schmidt condensation reaction and fully characterized by IR, NMR spectroscopy and GC-MS analysis. Also was subsequently subjected to comprehensive photophysical and computational studies. For the photophysical characterization, the molar absorptivity coefficients and fluorescence quantum yields in methanol, acetonitrile, and chloroform were determined, along with an analysis of solvatochromic and solvatofluorochromic effects in different solvents and the assessment of the Stokes shift. The compound exhibited positive solvatochromism and solvatofluorochromism, providing valuable information on its polarity-dependent behavior. Computational analysis based on density functional theory elucidated the energy gaps between the boundary molecular orbitals and the electrostatic potential map, which corresponded to the structure of the compound and the trends observed in the photophysical study.