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Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
Thiophene-containing Pechmann dye derivatives
Tyler B Norsten1, Eric Assen B Kantchev, Michael B Sullivan
1Institute of Materials Research and Engineering, A*STAR, 3 Research Link, Singapore 117602. norstent@imre.a-star.edu.sg
Abstract:
Thiophene-containing Pechmann dyes (unsaturated exo-5,5-dilactones) were easily prepared by Cu-catalyzed dehydration of the corresponding β-aroylacrylic acids. Introduction of long alkyl chains greatly enhances solubility. Isomerization of an alkyl-substituted thiophene Pechmann dye (TPD) gave the corresponding endo-6,6-dilactone. The redox and electronic properties of these new dyes were investigated by CV, UV/vis, and fluorescence spectroscopy and DFT and TD-DFT computations. Strong absorption and emission in the visible region were recorded.
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