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Synthesis and Photophysical Properties of N ‐Arylated Diketopyrrolopyrroles
Author(s) -
Gutkowski Krzysztof,
Azarias Cloé,
Banasiewicz Marzena,
Kozankiewicz Bolesław,
Jacquemin Denis,
Gryko Daniel T.
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701593
Subject(s) - chemistry , fluorescence , solid state , density functional theory , aryl , alkylation , nitro , medicinal chemistry , photochemistry , computational chemistry , organic chemistry , catalysis , alkyl , physics , quantum mechanics
The N ‐arylation of diketopyrrolopyrroles with aryl fluorides free of nitro groups was successfully achieved for the first time. Diketopyrrolopyrroles possessing 3,4‐dimethoxyphenyl and benzofuryl substituents underwent reaction with, for example, pentafluoropyridine, in the presence of K 2 CO 3 in N ‐methyl‐2‐pyrrolidone to give the desired products in moderate yields. Their photophysical properties in solution were found not to differ significantly from those of analogous N ‐alkylated diketopyrrolopyrroles, whereas in contrast to the latter compounds, they were found to possess fluorescence in the solid state. The photophysical properties of all compounds were rationalized by using time‐dependent density functional theory.