Phenylboronic Acid

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Kwangnak Koh - One of the best experts on this subject based on the ideXlab platform.

  • Formation and Characterization of Self-Assembled Phenylboronic Acid Derivative Monolayers toward Developing Monosaccharide Sensing-Interface
    Sensors, 2007
    Co-Authors: Hongxia Chen, Minsu Lee, Jae-ho Kim, Jaebeom Lee, Yeong-soon Gal, Yoon-hwae Hwang, Kwangnak Koh
    Abstract:

    We designed and synthesized Phenylboronic Acid as a molecular recognitionmodel system for saccharide detection. The Phenylboronic Acid derivatives that haveboronic Acid moiety are well known to interact with saccharides in aqueous solution; thus,they can be applied to a functional interface of saccharide sensing through the formation ofself-assembled monolayer (SAM). In this study, self-assembled Phenylboronic Acidderivative monolayers were formed on Au surface and carefully characterized by atomicforce microscopy (AFM), Fourier transform infrared reflection absorption spectroscopy(FTIR-RAS), surface enhanced Raman spectroscopy (SERS), and surface electrochemicalmeasurements. The saccharide sensing application was investigated using surface plasmonresonance (SPR) spectroscopy. The Phenylboronic Acid monolayers showed goodsensitivity of monosaccharide sensing even at the low concentration range (1.0 × 10-12 M).The SPR angle shift derived from interaction between Phenylboronic Acid andmonosaccharide was increased with increasing the alkyl spacer length of synthesizedPhenylboronic Acid derivatives.

  • Monosaccharides Sensing Characteristics of Phenylboronic Acid Monolayers
    Molecular Crystals and Liquid Crystals, 2002
    Co-Authors: Minsu Lee, Youngjune Hur, Jae-ho Kim, Heung-jin Choi, Kwangnak Koh
    Abstract:

    To detect low concentrations of sugars, Phenylboronic Acid derivatives were synthesized and their self-assembled monolayers (SAM) were formed on a gold surface. Monosaccharides sensing with the constructed Phenylboronic Acid monolayers were evaluated through the surface plasmon resonance (SPR) technique. These Phenylboronic Acid monolayers showed good sensitivity and selectivity to detect fructose at low concentrations.

  • Surface plasmon resonance study on the interaction between the fructose and Phenylboronic Acid monolayer
    Microchemical Journal, 2002
    Co-Authors: Minsu Lee, Youngjune Hur, Jae-ho Kim, Heung-jin Choi, Tae-il Kim, Kyung-ho Kim, Kwangnak Koh
    Abstract:

    Phenylboronic Acid derivatives were synthesized and their self-assembled monolayers (SAMs) were formed on a gold surface. The interaction between fructose and Phenylboronic Acid monolayers was evaluated using surface plasmon resonance (SPR). These Phenylboronic Acid monolayers showed good sensitivity to fructose at a low concentration range and the resonance angle shifts increased in accordance with the alkyl chain length.

Nicholas E. Leadbeater - One of the best experts on this subject based on the ideXlab platform.

Yuming Zhao - One of the best experts on this subject based on the ideXlab platform.

Hidehiro Sakurai - One of the best experts on this subject based on the ideXlab platform.

  • Mechanism of the Aerobic Homocoupling of Phenylboronic Acid on Au20−: A DFT Study
    Chemistry an Asian journal, 2015
    Co-Authors: Sangita Karanjit, Masahiro Ehara, Hidehiro Sakurai
    Abstract:

    The mechanism of the gold nanocluster-catalyzed aerobic homocoupling of arylboronic Acids has been elucidated by means of DFT calculations with Au20(-) as a model cluster for the Au:[poly(N-vinylpyrrolidin-2-one)] catalyst. We found that oxygen affects the adsorption of Phenylboronic Acid and, by lowering the energy barrier, a water molecule enhances dissociation of the C-B bond, which is probably the rate-determining step. The key role of oxygen is in activating the surface of the gold cluster by generating Lewis Acidic sites for adsorption and activation of the Phenylboronic Acid, leading to the formation of biphenyl through a superoxo-like species. Moreover, the oxygen adsorbed on the Au nanocluster can act as an oxidant for Phenylboronic Acid, giving phenol as a byproduct. As shown by NBO analysis, the basic aqueous reaction medium facilitates the reductive elimination process by weakening the Au-C bond, thereby enhancing the formation of biphenyl. The coupling of phenyl and reductive elimination of biphenyl occur at the top or facet site with low-energy-barrier through spillover of phenyl group on Au NC. The present findings are useful for the interpretation or design of other coupling reactions with Au NC.

  • Aerobic oxygenation of Phenylboronic Acid promoted by thiol derivatives under gold-free conditions: a warning against gold nanoparticle catalysis
    Tetrahedron Letters, 2012
    Co-Authors: Patcharin Kaewmati, Ekasith Somsook, Raghu Nath Dhital, Hidehiro Sakurai
    Abstract:

    Abstract Oxygenation of Phenylboronic Acid to phenol is promoted by thiol derivatives such as 2-aminothiophenol under aerobic conditions in water without metal catalyst. A plausible mechanism involves autoxidation of thiol to generate hydrogen peroxide in situ, which converts Phenylboronic Acid into phenol under basic conditions. Since thiols are often utilized as protective ligands for gold nanoparticles (AuNPs), this result is a warning that excess thiols and free thiols liberated from the Au surface could participate in aerobic oxidations catalyzed by thiol-protected AuNPs.

Minsu Lee - One of the best experts on this subject based on the ideXlab platform.

  • Formation and Characterization of Self-Assembled Phenylboronic Acid Derivative Monolayers toward Developing Monosaccharide Sensing-Interface
    Sensors, 2007
    Co-Authors: Hongxia Chen, Minsu Lee, Jae-ho Kim, Jaebeom Lee, Yeong-soon Gal, Yoon-hwae Hwang, Kwangnak Koh
    Abstract:

    We designed and synthesized Phenylboronic Acid as a molecular recognitionmodel system for saccharide detection. The Phenylboronic Acid derivatives that haveboronic Acid moiety are well known to interact with saccharides in aqueous solution; thus,they can be applied to a functional interface of saccharide sensing through the formation ofself-assembled monolayer (SAM). In this study, self-assembled Phenylboronic Acidderivative monolayers were formed on Au surface and carefully characterized by atomicforce microscopy (AFM), Fourier transform infrared reflection absorption spectroscopy(FTIR-RAS), surface enhanced Raman spectroscopy (SERS), and surface electrochemicalmeasurements. The saccharide sensing application was investigated using surface plasmonresonance (SPR) spectroscopy. The Phenylboronic Acid monolayers showed goodsensitivity of monosaccharide sensing even at the low concentration range (1.0 × 10-12 M).The SPR angle shift derived from interaction between Phenylboronic Acid andmonosaccharide was increased with increasing the alkyl spacer length of synthesizedPhenylboronic Acid derivatives.

  • Monosaccharides Sensing Characteristics of Phenylboronic Acid Monolayers
    Molecular Crystals and Liquid Crystals, 2002
    Co-Authors: Minsu Lee, Youngjune Hur, Jae-ho Kim, Heung-jin Choi, Kwangnak Koh
    Abstract:

    To detect low concentrations of sugars, Phenylboronic Acid derivatives were synthesized and their self-assembled monolayers (SAM) were formed on a gold surface. Monosaccharides sensing with the constructed Phenylboronic Acid monolayers were evaluated through the surface plasmon resonance (SPR) technique. These Phenylboronic Acid monolayers showed good sensitivity and selectivity to detect fructose at low concentrations.

  • Surface plasmon resonance study on the interaction between the fructose and Phenylboronic Acid monolayer
    Microchemical Journal, 2002
    Co-Authors: Minsu Lee, Youngjune Hur, Jae-ho Kim, Heung-jin Choi, Tae-il Kim, Kyung-ho Kim, Kwangnak Koh
    Abstract:

    Phenylboronic Acid derivatives were synthesized and their self-assembled monolayers (SAMs) were formed on a gold surface. The interaction between fructose and Phenylboronic Acid monolayers was evaluated using surface plasmon resonance (SPR). These Phenylboronic Acid monolayers showed good sensitivity to fructose at a low concentration range and the resonance angle shifts increased in accordance with the alkyl chain length.