Synthesis and spectroscopic study of highly fluorescent β-enaminone based boron complexes

Kumbhar, Haribhau S.; Gadilohar, Balu L.; Shankarling, Ganapati S.

doi:10.1016/j.saa.2015.03.044

Cited by 23 publications

(14 citation statements)

References 68 publications

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“…As shown in Figure a, all of the absorption bands are mainly located in the range of 300–400 nm, which could be derived from S 0 –S 1 transitions . However, the emission peaks of the boron compounds basically range from 380 to 580 nm, owing to the π-electron delocalization of B 3– , which are symmetric as mirror images of the absorption spectra . In addition, compounds 1 – 5 exhibit large Stokes shifts of 103, 95, 86, 83, and 76 nm, respectively, indicating that the as-prepared boron compounds possess the advantage of a relatively wide adjustable range of fluorescence color.…”

Section: Results and Discussionmentioning

confidence: 97%

Ammonium Arylspiroborate Compounds: Synthesis, Crystal Structure, Fluorescence Properties, and Antibacterial Activity

Wang

Zhou

2017

Organometallics

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A series of R-substituted ammonium arylspiroborate compounds (R = CH 3 , H, F, Cl, Br) have been synthesized via a facile one-pot method. The structures of these new kinds of boron compounds were characterized by IR, NMR spectra, elemental analysis and X-ray diffraction techniques, and their possible formation mechanism was proposed. Surprisingly, the as-synthesized boron compounds showed multifunctional character with not only excellent fluorescence properties (high quantum yields and large Stokes shift) in both the liquid and solid state but also high antibacterial activity against both Gram-negative (E. coli) and Gram-positive (S. aureus) bacteria. The chlorine-substituted boron compound even possessed antibacterial activity comparable with that of commercial antibiotics. More importantly, the fluorescence properties and antibacterial activity of these boron compounds could be easily mediated by the variation of the substituents, which was proved to regulate the conjugated system, modify the hydrophobic character, and adjust the electric charge on the surface of boron compounds. In addition, the influence of different factors including solvent (i.e., polarity, concentration), temperature, and pH on the fluorescence properties of boron compounds was discussed in detail. This work provides a new strategy for the design of multifunctional organoboron compounds and the mediation of their properties.

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Section: Results and Discussionmentioning

confidence: 97%

Ammonium Arylspiroborate Compounds: Synthesis, Crystal Structure, Fluorescence Properties, and Antibacterial Activity

Wang

Zhou

2017

Organometallics

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“…These difluoroboron complexes of b-enaminones, which belong to the family of b-iminoenolate boron complexes (Kubota et al, 2011), have attracted attention as a promising class of fluorophores (Josefik et al, 2012). Shankarling et al described the synthesis and spectral and electrochemical characterization of some boron difluoride complexes of benzoindoline-based b-enaminones (Kumbhar et al, 2015). In 2008, Xia et al reported excellent solution-state fluorescence for some heterocyclic b-iminoenolates (Xia et al, 2008).…”

Section: Introductionmentioning

confidence: 99%

“…Shankarling et al described the synthesis and spectral and electrochemical characterization of some boron difluoride complexes of benzoindoline-based β-enaminones ( Kumbhar et al, 2015 ). In 2008, Xia et al reported excellent solution-state fluorescence for some heterocyclic β-iminoenolates ( Xia et al, 2008 ).…”

Section: Introductionmentioning

confidence: 99%

Novel Alkyl(aryl)-Substituted 2,2-Difluoro-6-(trichloromethyl)-2H-1,3,2-oxazaborinin-3-ium-2-uides: Synthesis, Antimicrobial Activity, and CT-DNA Binding Evaluations

et al. 2020

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The synthesis, antimicrobial activity evaluations, biomolecule-binding properties (DNA), and absorption and emission properties of a new series of (Z)-1,1,1-trichloro-4-alkyl(aryl) amino-4-arylbut-3-en-2-ones (4, 5) and 2,2-difluoro-3-alkyl(aryl)amino-4-aryl-6-(trichloromethyl)-2H-1,3,2-oxazaborinin-3-ium-2-uides (6, 7) in which 3(4)-alkyl(aryl) = H, Me, iso-propyl, n-butyl, C 6 H 5 , 4-CH 3 C 6 H 4 , 4-CH 3 OC 6 H 4 , 4-NO 2 C 6 H 4 , 4-FC 6 H 4 , 4-BrC 6 H 4 , 2-naphthyl, is reported. A series of b-enaminoketones (4, 5) is synthesized from the O,N-exchange reaction of some amines (3) with (Z)-1,1,1-trichloro-4-methoxy-4-arylbut-3-en-2-ones (1, 2) at 61-90% yields. Subsequently, reactions of the resulting benaminoketones with an appropriate source of boron (BF 3 .OEt 2) gave the corresponding oxazaborinine derivatives (6, 7) at 50-91% yields. UV-Vis and emission properties of biomolecule-binding properties for the DNA of these new BF 2-b-enamino containing CCl 3 units were also evaluated. Some compounds from the present series also exhibited potent antimicrobial effects on various pathogenic microorganisms at concentrations below those that showed cytotoxic effects. Compounds 4d, 4e, 6e, and 6f showed the best results and are very significant against P. zopfii, which causes diseases in humans and animals.

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“…Hence, they seldom exhibit photoluminescence in the solid state [31]. Other than BODIPY, the boron complexes of pyridomethene [32], diketone [33], iminoketone [34], azo dyes [35], β-enaminone [36] and β-ketoiminate also shows high fluorescence. Some of them also show photoluminescence in the solid state as well as aggregation induced emission enhancement (AIEE) [37].…”

Section: Introductionmentioning

confidence: 99%

Aggregation induced emission (AIE) active β-ketoiminate boron complexes: Synthesis, photophysical and electrochemical properties

Kumbhar

Shankarling

2015

Dyes and Pigments

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Synthesis and spectroscopic study of highly fluorescent β-enaminone based boron complexes

Cited by 23 publications

References 68 publications

Ammonium Arylspiroborate Compounds: Synthesis, Crystal Structure, Fluorescence Properties, and Antibacterial Activity

Ammonium Arylspiroborate Compounds: Synthesis, Crystal Structure, Fluorescence Properties, and Antibacterial Activity

Novel Alkyl(aryl)-Substituted 2,2-Difluoro-6-(trichloromethyl)-2H-1,3,2-oxazaborinin-3-ium-2-uides: Synthesis, Antimicrobial Activity, and CT-DNA Binding Evaluations

Aggregation induced emission (AIE) active β-ketoiminate boron complexes: Synthesis, photophysical and electrochemical properties

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