Stilbazolium Boronic Acid/Borate - A New Stilbazolium Betaine Dye: An Optical Molecular Sensor for Monosaccharides

Satô, Kiyoshi; Sone, Akiko; Arai, Sadao; Yamagishi, Takamichi

doi:10.3987/com-03-s25

Cited by 6 publications

(3 citation statements)

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“…Sato et al developed stilbazoliumboronic acids 81 and 82 and then evaluated these units for saccharide sensing. Wang and co-workers have used nitrophenolboronic acids, which show large UV shifts upon addition of saccharides.…”

Section: Boronic Acids For Sensing Applicationsmentioning

confidence: 99%

“…The pK a of 80 (7.81) was much less than that of azo dye 75 (10.2), which means that a visible color change could be observed at pH 8.21. 120 Sato et al 121 developed stilbazoliumboronic acids 81 and 82 and then evaluated these units for saccharide sensing. Wang and co-workers 122 have used nitrophenolboronic acids, which show large UV shifts upon addition of saccharides.…”

Section: Chemical Reviewsmentioning

confidence: 99%

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Glucose Sensing in Supramolecular Chemistry

2015

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Section: Boronic Acids For Sensing Applicationsmentioning

confidence: 99%

Section: Chemical Reviewsmentioning

confidence: 99%

Glucose Sensing in Supramolecular Chemistry

2015

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“…Several π-chromophoric compounds with a boron moiety not directly bound to the chromophore have been prepared, i.e., colorimetric internal charge-transfer (ICT) carbohydrate sensors . A large number of chromophoric compounds containing sp 2 -hybridized boron moieties directly bound to a conjugated π-electron system were synthesized during the past decade. − Derivatives of arylboronic acids, arylboronate esters, and triarylboranes belong to these classes of compounds in which the vacant p-orbital of the boron atom participates in the aromatic system. Azo compounds, Schiff bases, stilbenes, and related compounds 8 were reported with directly bound boronic acid or boronate ester moieties.…”

Section: Introductionmentioning

confidence: 99%

Nitro-Substituted Stilbeneboronate Pinacol Esters and Their Fluoro-Adducts. Fluoride Ion Induced Polarity Enhancement of Arylboronate Esters

et al. 2007

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A series of stilbeneboronate pinacol cyclic esters, containing none to three nitro groups, have been synthesized by various olefination reactions and characterized by X-ray single-crystal structure analysis. A stilbeneboronate ester bearing electron-acceptor groups experiences transition to a push-pull pi-electron system upon complexation with one fluoride ion at the boron atom. The UV-vis absorption maxima of the presented nitro-substituted stilbeneboronate esters are red-shifted upon addition of fluoride ions, indicating this binding event. The enhancement of the polarity of the investigated compounds and the changes in the electronic system were investigated by UV-vis absorption spectroscopy and solvatochromism. Additionally, studies were performed by natural bond orbital (NBO) analysis and RI-CC2 calculations of the vertical excitation energies. The synergism of fluoride ion complexation and solvation upon the UV-vis band shift is interpreted in terms of linear solvation energy relationships (LSERs) using the Kamlet-Taft solvent parameter set. It is found that the UV-vis absorption of the fluoro-boronates is strongly dependent on the solvents hydrogen-bond donating ability.

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Boronic Acid‐Based Receptors

Fossey

James

2012

Supramolecular Chemistry

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The ability to monitor analytes within physiological, environmental, and industrial scenarios is of prime importance. As recognition events occur on a molecular level, gathering and processing the information poses a fundamental challenge. Therefore, robust chemical molecular sensors, known as “chemosensors,” with the capacity to detect chosen molecules selectively and signal this presence continue to attract considerable attention. Real‐time monitoring of saccharides is of particular interest, such as D ‐glucose in blood. Toward that end, the covalent coupling interaction between boronic acids and saccharides has been exploited with some success to monitor the presence of such saccharides. The boronic acid–and Lewis acid base interaction is also suitable for the capture and recognition of anions. Anions are involved in fundamental processes in all living things. Our aim as synthetic chemists is to mimic nature s level of sophistication in designing and producing chemosensors capable of determining the concentration of a target analyte (i.e., saccharides and anions) in any medium.

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Stilbazolium Boronic Acid/Borate - A New Stilbazolium Betaine Dye: An Optical Molecular Sensor for Monosaccharides

Cited by 6 publications

References 20 publications

Glucose Sensing in Supramolecular Chemistry

Glucose Sensing in Supramolecular Chemistry

Nitro-Substituted Stilbeneboronate Pinacol Esters and Their Fluoro-Adducts. Fluoride Ion Induced Polarity Enhancement of Arylboronate Esters

Boronic Acid‐Based Receptors

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