4.7 Article

Abnormal push-pull benzo[4,5]imidazo[1,2-a][1,2,3]triazolo[4,5-e] pyrimidine fluorophores in planarized intramolecular charge transfer (PLICT) state: Synthesis, photophysical studies and theoretical calculations

期刊

DYES AND PIGMENTS
卷 204, 期 -, 页码 -

出版社

ELSEVIER SCI LTD
DOI: 10.1016/j.dyepig.2022.110405

关键词

Push-pull fluorophores; Charge transfer; Solvent effect; Aggregation; Acidochromic effect; Azoloazine

资金

  1. Russian Science Foundation [21-13-00304]
  2. Grants Council of the President of the Russian Federation [NSh-1223.2022.1.3]
  3. IMM UB RAS
  4. RUDN University Strategic Academic Leadership Program
  5. Russian Science Foundation [21-13-00304] Funding Source: Russian Science Foundation

向作者/读者索取更多资源

This study designed a series of fluorophores with high luminescence efficiency, solvatochromic effect, and aggregation induced emission. Among them, fluorophore 4h showed the best solvatochromic effect, while probe 4f exhibited the most pronounced aggregation induced emission characteristics.
The combination of excellent luminescence with high solvent polarity effect and aggregation induced emission (AIE) is an ideal combination for creating fluorophores/probes with high microenvironmental sensitivity. However, many push-pull chromophores of the D-A type in common intramolecular charge transfer (ICT) state with a significant solvatochromic effect and AIE activity, have poor luminescent properties. Herein, to overcome this problem by using reactions of nucleophilic aromatic hydrogen substitution (S-N(H)), we have designed a series of novel 4-heteroaryl-substituted 2-aryl-2H-benzo[4,5]imidazo[1,2-a][1,2,3]triazolo[4,5-e]pyrimidine fluorophores possessing a planarized intramolecular charge transfer (PLICT) state. All these fluorophores exhibited high luminescence quantum yields (up to 60%) and large Stokes shift values of up to 7459 cm(-1). Among them, the fluorophore 4h was found to exhibit the most pronounced positive solvatochromic effect and the probe 4f exhibited the most pronounced aggregation induced emission characteristics. This AIE behavior was further confirmed by means of time-resolved fluorescence lifetime measurements as well as DFT-assisted geometry optimization studies. In the presence of trifluoroacetic acid (TFA) compound 4h exhibited a well-pronounced acidochromism via visible color change from yellow-green to orange which returned to the original yellow green solution after the addition of triethylamine (TEA). The Stern-Volmer constant for the probe 4h towards TFA was 38 M-1. Finally, for the compounds 4f, g, h theoretical calculations in the ground and excited states in different solvents were carried out to confirm the PLICT process. Based on all above the herein reported PLICT fluorophores 4a-h can be successfully applied as biological probes and optical switches.

作者

我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。

评论

主要评分

4.7
评分不足

次要评分

新颖性
-
重要性
-
科学严谨性
-
评价这篇论文

推荐

暂无数据
暂无数据