A Family of Highly Fluorescent and Membrane-Permeable Bis(BF2) Acyl-Pyridinylhydrazine Dyes with Strong Solid-State Emission and Large Stokes Shifts: The BOAPH Fluorophores,The Journal of Organic Chemistry

当前位置： X-MOL 学术 › J. Org. Chem. › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

A Family of Highly Fluorescent and Membrane-Permeable Bis(BF2) Acyl-Pyridinylhydrazine Dyes with Strong Solid-State Emission and Large Stokes Shifts: The BOAPH Fluorophores
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2021-08-03 , DOI: 10.1021/acs.joc.1c01042
Changjiang Yu _{1,

2,

3} , Xingbao Fang ₁ , Hua Wang ₁ , Xing Guo ₁ , Lilin Sun ₁ , Qinghua Wu ₁ , Lijuan Jiao ₁ , Erhong Hao ₁

Affiliation

Organic small-molecule fluorescent chromophores have become essential to modern chemical, biological, and materials related investigations. Herein, a straightforward synthesis and subsequent borylation were presented to form a novel family of bisBF₂-anchoring acyl-pyridinylhydrazine, which we named BOAPH. The chromophore enjoys outstanding structural diversities owing to varied acyl chlorides and N-heteroarenylhydrazides. These resultant BOAPH dyes are confirmed by NMR, HRMS, and single-crystal X-ray structure analysis. Their spectroscopic properties were studied, and most of the strong absorbance and bright fluorescence with maximum wavelengths centered in the range of 400 and 650 nm. More importantly, they exhibit promising fluorescence quantum yields up to 0.79 in solution and solid states, good photostability, and large Stokes shifts. Furthermore, a respective BOAPH dye with a para-dimethylaminophenyl group exhibited the interesting ability of ultrafast staining and two-photon imaging, which can specifically label lipid droplets of living cells immediately without the need for incubation.

中文翻译：

一系列具有强固态发射和大斯托克斯位移的高荧光和透膜双 (BF2) 酰基吡啶基肼染料：BOAPH 荧光团

有机小分子荧光发色团已成为现代化学、生物和材料相关研究的必要条件。在此，提出了一种直接的合成和随后的硼酸化，以形成一个新的 bisBF _{2 -}锚定酰基吡啶基肼家族，我们将其命名为 BOAPH。由于不同的酰氯和N，发色团具有突出的结构多样性-杂芳基酰肼。这些所得 BOAPH 染料通过 NMR、HRMS 和单晶 X 射线结构分析得到证实。研究了它们的光谱特性，并且大部分强吸光度和明亮的荧光最大波长集中在 400 和 650 nm 范围内。更重要的是，它们在溶液和固态下表现出高达 0.79 的有希望的荧光量子产率、良好的光稳定性和大的斯托克斯位移。此外，用相应的BOAPH染料对-dimethylaminophenyl组表现出超快染色和双光子成像的有趣能力，其可以特异性标记活细胞的脂滴立即而不需要孵育。

更新日期：2021-09-03

点击分享查看原文

点击收藏

阅读更多本刊新发论文