| Abstract [eng] |
The main goal of the present work was to synthesize pyrrolo[2,3-d]pyrimidine core based oligoarylenes and to evaluate their photophysical properties. As a result, the Suzuki reaction of 2,4-dichloropyrrolo[2,3-d]pyrimidine with arylboronic acids was studied and novel 4-aryl- and 2,4-diarylpyrrolo[2,3-d]pyrimidines were synthesized. The reaction conditions including an effective catalyst system for the Suzuki cross-coupling reaction were proposed to achieve site-selectivity of the reaction studied. A general approach for the preparation of 2,4,7-triarylpyrrolo[2,3-d]pyrimidines, bis(pyrrolo[2,3-d]pyrimidin-7-yl)carbazoles and -fluorenes were developed by copper-catalyzed N-arylation reaction of 2,4-diarylpyrrolo[2,3-d]pyrimidines with aryl halogenides, dihalocarbazoles or dihalofluorenes. Synthetic strategies leading to pyrrolo[2,3-d]pyrimidines with different aryl moieties in positions 2, 4 and 7 of the heterocycle were studied and an efficient method for their synthesis was developed. The synthesized pyrrolo[2,3-d]pyrimidine-core based oligoarylenes were found to exhibit blue-UV fluorescence in solution and in solid state. Influence of structure of aryl groups, their position in the pyrrolo[2,3-d]pyrimidine nucleous and extent of pi-conjugated aromatic system on the photoluminescent characteristics were evaluated. Some pyrrolo[2,3-d]pyrimidine derivatives were found to exhibit positive solvatofluorochromism and to form nanoaggregates in THF/water mixtures with aggregation induced enhanced emission. Pyrrolo[2,3-d]pyrimidine-core based oligomers with pi-extended conjugation system were found to exibit better fluorescence quantum yields in a solid state than in solution. |
