Related Experiment Video
Updated: May 9, 2026

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
Preparation and pH-switching of fluorescent borylated arylisoquinolines for multilevel molecular logic
Vânia F Pais1, Mauricio Lineros, Rocío López-Rodríguez
1CIQSO-Center for Research in Sustainable Chemistry and Department of Chemical Engineering, Physical Chemistry, and Organic Chemistry, University of Huelva, Campus de El Carmen s/n, 21071 Huelva, Spain.
Abstract:
The preparation of pH-switchable fluorescent borylated arylisoquinoline dyes via a flexible iridium-catalyzed route is reported. The obtained dyes feature aromatic amino substitution and lateral aliphatic amino groups as electron donors. The photophysical properties of the internal charge transfer dyes were studied, which was complemented by density functional theory calculations. Appreciable fluorescence quantum yields (Φf up to ca. 0.4) and characteristic spectral fingerprints in the green to red emission range were observed. The fluorescence modulation upon multiple and orthogonal protonation with triflic acid was studied and led to the interpretation of multilevel switching including off-on-off, ternary, and quaternary responses.
More Related Videos
Related Concept Videos
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Variables Affecting Phosphorescence and Fluorescence
Aryldiazonium Salts to Azo Dyes: Diazo Coupling
Preparation of Diols and Pinacol Rearrangement
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

