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Synthesis and photophysical properties of 2-azolyl-6-piperidinylpurines

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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This work was supported by the ERDF 1.1.1.1 activity project No. 1.1.1.1/16/A/131 “Design and Investigation of Light Emitting and Solution Processable Organic Molecular Glasses”.

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Authors and Affiliations

  1. Faculty of Materials Science and Applied Chemistry, Riga Technical University, 3 Paula Valdena St, Riga, LV-1048, Latvia

    Armands Sebris, Kaspars Traskovskis, Irina Novosjolova & Māris Turks

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  1. Armands Sebris
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  2. Kaspars Traskovskis
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  3. Irina Novosjolova
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  4. Māris Turks
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Corresponding authors

Correspondence to Irina Novosjolova or Māris Turks.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2021, 57(5), 560–567

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Sebris, A., Traskovskis, K., Novosjolova, I. et al. Synthesis and photophysical properties of 2-azolyl-6-piperidinylpurines. Chem Heterocycl Comp 57, 560–567 (2021). https://doi.org/10.1007/s10593-021-02943-1

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