Related Experiment Video
Updated: Jun 30, 2025

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
Benzazole-Based ESIPT Fluorophores: Proton Transfer from the Chalcogen Perspective. A Combined Theoretical and
Louise Kommers Reimann1, Bianca Thaís Dalberto1, Paulo Henrique Schneider1
1Instituto de Química, Departamento de Química Orgânica, Universidade Federal Do Rio Grande Do Sul (UFRGS), PO Box 15003, Porto Alegre, Rio Grande Do Sul, ZIP Code91501-970, Brazil.
Abstract:
In this study, we present a comprehensive photophysical investigation of ESIPT-reactive benzazole derivatives in both solution and the solid state. These derivatives incorporate different chalcogen atoms (O, S, and Se) into their structures, and we explore how these variations impact their electronic properties in both ground and excited states. Changes in the UV-Vis absorption and fluorescence emission spectra were analyzed and correlated with the chalcogen atom and solvent polarity. In general, the spectral band of the benzazole derivative containing selenium was redshifted in both the ground and excited states compared to that of its oxygen and sulfur counterparts. Furthermore, we observed that the solvent played a distinctive role in influencing the ESIPT process within these compounds, underscoring once again the significant influence of the chalcogen atom on their photophysical behavior. Theoretical calculations provided a deeper understanding of the molecular dynamics, electronic structures, and photophysical properties of these compounds. These calculations highlighted the effect of chalcogen atoms on the molecular geometry, absorption and emission characteristics, and intramolecular hydrogen bonding, revealing intricate details of the ESIPT mechanism. The integration of experimental and computational data offers a detailed view of the structural and electronic factors governing the photophysical behavior of benzazole derivatives.
More Related Videos
Related Concept Videos
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene
NMR Spectroscopy of Benzene Derivatives
Variables Affecting Phosphorescence and Fluorescence
Electrophilic Aromatic Substitution: Sulfonation of Benzene
Reactions at the Benzylic Position: Halogenation

