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Issue 3, 2018
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1,1-Difluoro-3-aryl(heteroaryl)-1H-pyrido[1,2-c][1,3,5,2]oxadiazaborinin-9-ium-1-uides: synthesis; structure; and photophysical, electrochemical, and BSA-binding studies

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Abstract

This paper presents a series of six examples of 1,1-difluoro-3-aryl(heteroaryl)-1H-pyrido[1,2-c][1,3,5,2]oxadiazaborinin-9-ium-1-uides (2)—in which aryl(heteroaryl) = phenyl, 4-MeC6H4, 4-N(CH3)2C6H4, 4-NO2C6H4, 2-naphthyl, and 2-thienyl—as pyridine-based boron heterocycles with variable ligand structures. The heterocycles 2 were easily synthesized at yields of 51–70% from reactions—at room temperature for 24 h—of simple N-(pyridin-2-yl)benzamides (1) with BF3·Et2O, and they were fully characterized by 1H-, 13C-, 19F-, and 11B-NMR spectroscopy, GC-MS, and X-ray diffractometry. The optical and electrochemical properties of 2 (UV-vis spectra, fluorescence spectra, quantum yield calculations, Stokes’ shifts, redox potentials, and DFT calculations) were determined and discussed. BSA-binding experiments and molecular docking studies of new complexes 2 were performed and correlated between each other.

Graphical abstract: 1,1-Difluoro-3-aryl(heteroaryl)-1H-pyrido[1,2-c][1,3,5,2]oxadiazaborinin-9-ium-1-uides: synthesis; structure; and photophysical, electrochemical, and BSA-binding studies

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Publication details

The article was received on 18 Oct 2017, accepted on 21 Dec 2017 and first published on 21 Dec 2017


Article type: Paper
DOI: 10.1039/C7NJ04032F
Citation: New J. Chem., 2018,42, 1913-1920
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    1,1-Difluoro-3-aryl(heteroaryl)-1H-pyrido[1,2-c][1,3,5,2]oxadiazaborinin-9-ium-1-uides: synthesis; structure; and photophysical, electrochemical, and BSA-binding studies

    H. G. Bonacorso, T. P. Calheiro, B. A. Iglesias, T. V. Acunha, S. Z. Franceschini, A. Ketzer, A. R. Meyer, L. V. Rodrigues, P. A. Nogara, J. B. T. Rocha, N. Zanatta and M. A. P. Martins, New J. Chem., 2018, 42, 1913
    DOI: 10.1039/C7NJ04032F

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