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Synthesis and photophysical properties of 2-azolyl-6-piperidinylpurines
Chemistry of Heterocyclic Compounds ( IF 1.5 ) 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.



中文翻译:

2-唑基-6-哌啶基嘌呤的合成及光物理性质

设计了一种新型荧光 2-唑基-6-哌啶基嘌呤衍生物的合成。嘌呤 C-2 原子上的唑基取代基是通过亲核芳香取代引入的或者在四唑基和 1,2,3-三唑基取代基的情况下,分别通过在预先安装的胺或叠氮化物部分上形成环来引入。使用Mitsunobu反应条件将获得的嘌呤中间体在N-9位官能化以获得无定形化合物,从而形成质量好的薄层膜。合成的推挽系统表现出荧光,发射范围为 360-400 nm,在 CH 2 Cl 2溶液中的量子产率高达 66%,在薄层膜中高达 45%。

更新日期:2021-06-07
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