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Synthesis and photophysical properties of 2-azolyl-6-piperidinylpurines
Chemistry of Heterocyclic Compounds  (IF1.277),  Pub Date : 2021-06-07, DOI: 10.1007/s10593-021-02943-1
Armands Sebris, Kaspars Traskovskis, Irina Novosjolova, Māris Turks

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.