Synthesis and photophysical properties of oligoarylenes with a pyrrolo[2,3-d]pyrimidine core |
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Authors: | Sigitas Tumkevicius Jelena Dodonova Viktoras Masevicius Saulius Jursenas |
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Affiliation: | a Department of Organic Chemistry, Vilnius University, Naugarduko 24, LT-03225 Vilnius, Lithuania b Institute of Applied Research, Vilnius University, Sauletekio 9-III, LT-10222 Vilnius, Lithuania |
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Abstract: | The palladium-catalyzed Suzuki-Miyaura reaction of 2,4-dichloropyrrolo[2,3-d]pyrimidine with aryl boronic acids has been studied. Pd(OAc)2/dicyclohexyl(2-biphenyl)phosphine/K3PO4 was found to be an efficient catalyst system to prepare 4-aryl-2-chloro- and 2,4-diarylpyrrolo[2,3-d]pyrimidines. Novel non-linear molecules consisting of a pyrrolo[2,3-d]pyrimidine core and aryl branches have been elucidated as blue light-emitters with fluorescence quantum yields ranging from 4% to 67% in THF solution. The impact of an electron-withdrawing t-BuOCO group attached to the pyrrole ring of pyrrolopyrimidine derivatives on optical properties is discussed. |
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Keywords: | Pyrrolopyrimidines Suzuki-Miyaura reaction Oligoarylenes Cross-coupling Fluorescence |
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