A Convenient Synthesis of Diketopyrrolopyrrole Dyes

Diketopyrrolo[3,4- ]pyrroles (DPP) are high-performance organic optoelectronic materials. They have applications in solar cells, fluorescent probes, bioimaging, photodynamic/photothermal therapy, and in many other areas. This article reports a convenient two-step synthesis of various DPP dyes from P...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2021-08, Vol.26 (16), p.4758
Main Authors: Almodôvar, Vitor A S, Tomé, Augusto C
Format: Article
Language:English
Subjects:
Chemical reactions
Chromatography
Cross coupling
diketopyrrolopyrrole
Dyes
Ferrari red
Fluorescence
Fluorescent indicators
Medical imaging
Optoelectronics
Pyrroles
Solar cells
Solvents
Suzuki–Miyaura reaction
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Summary:Diketopyrrolo[3,4- ]pyrroles (DPP) are high-performance organic optoelectronic materials. They have applications in solar cells, fluorescent probes, bioimaging, photodynamic/photothermal therapy, and in many other areas. This article reports a convenient two-step synthesis of various DPP dyes from Pigment Red 254, an inexpensive commercial pigment. The synthesis includes a Suzuki-Miyaura cross-coupling reaction of a bis(4-chlorophenyl)DPP derivative with aryl and hetaryl boronic acids under mild reaction conditions. The new dyes show large Stokes shifts and high fluorescence quantum yields, important features for their potential use in technical and biological applications.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules26164758