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SYNTHESIS AND PHOTOPHYSICAL PROPERTIES OF 2-AZOLYL-6-PIPERIDINYLPURINES

Armands Sebris, Kaspars Traskovskis, Irina Novosjolova, Māris Turks
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Abstract


A synthesis of novel fluorescent 2-azolyl-6-piperidinylpurine derivatives was designed. Azolyl substituent at purine C-2 atom was introduced via nucleophilic aromatic substitution or in the case of tetrazolyl and 1,2,3-triazolyl substituents via a ring formation on a preinstalled amine or azide moiety, respectively. The obtained purine intermediates were functionalized at N-9 position using Mitsunobu reaction conditions to achieve amorphous compounds, which form thin-layer films of good quality. The synthesized push-pull systems exhibited fluorescence with emission in range of 360–400 nm and quantum yields up to 66% in CH2Cl2 solution and up to 45% in the
thin-layer film.

Keywords


azoles; purines; fluorescence; nucleophilic aromatic substitution; ring formation.

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