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

Authors

  • Armands Sebris Faculty of Materials Science and Applied Chemistry, Riga Technical University, 3 Paula Valdena St., Riga LV-1048, Latvia
  • Kaspars Traskovskis Faculty of Materials Science and Applied Chemistry, Riga Technical University, 3 Paula Valdena St., Riga LV-1048, Latvia
  • Irina Novosjolova Faculty of Materials Science and Applied Chemistry, Riga Technical University, 3 Paula Valdena St., Riga LV-1048, Latvia
  • Māris Turks Faculty of Materials Science and Applied Chemistry, Riga Technical University, 3 Paula Valdena St., Riga LV-1048, Latvia

DOI:

https://doi.org/10.1007/6115

Keywords:

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

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.

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Published

2021-05-26

Issue

Vol. 57 No. 5 (2021)

Section

Original Papers