Fluorescent boron complexes based on new N,O-chelates as promising candidates for flow cytometry†,Organic & Biomolecular Chemistry

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Fluorescent boron complexes based on new N,O-chelates as promising candidates for flow cytometry†
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2018-06-22 00:00:00 , DOI: 10.1039/c8ob00868j
Kseniya I. Lugovik _{1,

2,

3} , Alexander K. Eltyshev _{1,

2,

3} , Polina O. Suntsova _{1,

2,

3} , Leonid T. Smoluk _{2,

3,

4,

5} , Anna V. Belousova _{1,

2,

3,

4,

5} , Maria V. Ulitko _{1,

2,

3} , Artem S. Minin _{1,

2,

3,

5,

6} , Pavel A. Slepukhin _{1,

2,

3,

5,

7} , Enrico Benassi _{8,

9,

10,

11} , Nataliya P. Belskaya _{1,

2,

3}

Affiliation

This study presents the synthesis and optical properties of a new class of bright green–yellow fluorescent dyes with potential applications in bioimaging. A facile synthetic route via the chelation of aryl(hetaryl)aminoacryloylthiophene scaffolds with a BF₂ fragment is presented. The photophysical properties of the dyes are attributed to the nature and position of electron-donating and electron-withdrawing substituents. Upon coordination to a BF₂ fragment, characteristic emission was observed, with λ_em ranging from 503 to 543 nm and quantum yields of 0.14–0.42. Compared with parent aryl(hetaryl)aminoacryloylthiophenes, a significant red shift in absorption (up to 480 nm in solution) and emission (up to 543 nm in solution and 610 nm in the solid state) and high chemical stability and photostability were observed. The electron-accepting character of the substituents on the terminal aromatic ring or replacing this fragment with pyridine or pyrazine moieties resulted in increased quantum yields. To gain insight into the electronic structures and optical properties, quantum mechanical calculations were performed. The results of (TD-)DFT calculations supported the structural and spectroscopic data and showed the features of electronic distribution in the frontier molecular orbitals and active electrophilic and nucleophilic sites in the compounds investigated. Synthesized BF₂ complexes are promising dyes for cell imaging and flow cytometry owing to their ready penetration and accumulation in cells.

中文翻译：

基于新的N，O-螯合物的荧光硼配合物有望成为流式细胞术的候选者†

这项研究提出了一种新型的亮绿色-黄色荧光染料的合成和光学性质，它们在生物成像中具有潜在的应用。提出了一种通过芳基（杂芳基）氨基丙烯酰基噻吩骨架与BF ₂片段螯合的简便合成路线。染料的光物理性质归因于给电子和吸电子取代基的性质和位置。一旦协调到BF ₂片段中，观察到特征发射，具有λ _EM波长范围为503至543 nm，量子产率为0.14-0.42。与母体芳基（杂芳基）氨基丙烯酰基噻吩相比，吸收（溶液中至多480 nm）和发射（溶液中至多543 nm，固态至多610 nm）的吸收和化学稳定性和光稳定性显着提高。末端芳族环上的取代基或用吡啶或吡嗪部分取代该片段的电子接受特性导致增加的量子产率。为了深入了解电子结构和光学性质，进行了量子力学计算。（TD-）DFT计算的结果支持了结构和光谱数据，并显示了所研究化合物在前沿分子轨道中的电子分布以及活性亲电子和亲核位点的特征。合成高炉_2种复合物因其易于渗透和在细胞中蓄积，是用于细胞成像和流式细胞术的有前途的染料。

更新日期：2018-06-22

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