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Issue 28, 2018
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Fluorescent boron complexes based on new N,O-chelates as promising candidates for flow cytometry

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Abstract

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 λem 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.

Graphical abstract: Fluorescent boron complexes based on new N,O-chelates as promising candidates for flow cytometry

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Publication details

The article was received on 13 Apr 2018, accepted on 21 Jun 2018 and first published on 22 Jun 2018


Article type: Paper
DOI: 10.1039/C8OB00868J
Citation: Org. Biomol. Chem., 2018,16, 5150-5162
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    Fluorescent boron complexes based on new N,O-chelates as promising candidates for flow cytometry

    K. I. Lugovik, A. K. Eltyshev, P. O. Suntsova, L. T. Smoluk, A. V. Belousova, M. V. Ulitko, A. S. Minin, P. A. Slepukhin, E. Benassi and N. P. Belskaya, Org. Biomol. Chem., 2018, 16, 5150
    DOI: 10.1039/C8OB00868J

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