1,4-Phenylenebisboronic Acid CAS 4612-26-4

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1,4-Phenylenebisboronic acid ( with the chemical formula C₆H₄(B(OH)₂)₂) is an important aromatic bifurcated boronic acid compound. It is formed by connecting two boronic acid groups (-B(OH)₂) at the ortho positions (1,4 positions) of the benzene ring, presenting as a white to off-white crystalline powder, with a melting point of approximately 300°C (decomposition). As a key reagent for the Suzuki-Miyaura coupling reaction, it is widely used in the construction of biphenyl compounds and conjugated polymers, such as the synthesis of organic light-emitting diodes (OLED) and semiconductor materials.

The boronic acid groups can undergo cross-coupling with halogenated aromatic compounds under the action of a palladium catalyst to form C-C bonds, while showing good water solubility and air stability (needs to be stored in a dry environment).

This compound can be obtained through the lithium-halide exchange reaction of 1,4-dibromo-benzene with tri-methyl-boronic acid ester, followed by acidic hydrolysis. In the field of medicine, it is used as an intermediate in the research and development of anti-tumor and anti-inflammatory drugs. Additionally, its boronic acid groups can reversibly bind with diol compounds and be applied in sugar recognition and sensor design. It should be noted that it may undergo deboronation or polymerization side reactions under strong acid/base conditions. During experiments, the pH and reaction temperature need to be strictly controlled.

One of the key applications of 1,4-phenylenebisboronic acid lies in its use as a cross-linking agent in the synthesis of polymers and materials science. The boronic acid groups can react with diols or other multifunctional compounds to form boronate esters, which serve as cross-links between polymer chains. This ability to cross-link makes it an important component in the development of advanced materials with enhanced properties such as mechanical strength, thermal stability, and responsiveness to external stimuli.

Furthermore, which has found applications in the field of bioscience and biotechnology. Due to its ability to bind selectively to carbohydrates and other biomolecules, this compound has been utilized in the design of biosensors, drug delivery systems, and other biotechnological applications.

Chemical properties:It is an organic compound containing two boronic acid groups, which has high stability and strong Lewis acidity. In aqueous solution, boronic acid groups can exist in two forms: neutral planar triangles and negatively charged tetrahedral borate forms. There is a certain balance between these two forms, which allows them to covalently bind with diols and form stable cyclic esters.

Sugar recognition mechanism:the recognition mechanism of it with carbohydrate molecules is mainly based on its covalent binding with the structure of diols. In aqueous solution, its boronic acid group can undergo a substitution reaction with the hydroxyl group of sugar molecules, forming a ring closure reaction and generating stable and hydrophilic phenylboronic acid esters. This binding force is significantly higher than other diol structures, so it is often used to detect carbohydrate substances.

Selection of instruments with functional advantages

Fluorescence sensor
Fluorescence sensor is a sensor that uses the principle of fluorescent substances emitting fluorescence under specific wavelength light excitation, and detects the analyte by measuring the fluorescence intensity or wavelength change. Due to its high binding affinity with sugar molecules, it is often used as a recognition element in fluorescence sensors.

Other fluorescent sensors
In addition to graphene quantum dot based fluorescence sensors, PBA can also be combined with other fluorescent substances to construct different types of fluorescence sensors. For example, the interaction between PBA and fluorescent substances such as quantum dots and organic dyes can be utilized to detect other sugars or biomolecules.

Hydrogen peroxide sensor:A novel electrochemical hydrogen peroxide (H2O2) biosensor can be developed by utilizing its specific interaction with glycoprotein molecules. By synthesizing disulfides containing phenylboronic acid groups (such as DTBA-PBA) and then fixing them on the surface of a gold electrode, a dense phenylboronic acid monolayer film is formed. When horseradish peroxidase (HRP) covalently binds to the membrane, it can be used for quantitative detection of H2O2. The experimental results show that the sensor exhibits a good linear relationship with the response current of H2O2 within a specific concentration range, and has high sensitivity and selectivity.

Glucose sensor based on photonic crystal:A novel glucose sensor can be constructed by synthesizing photonic crystal materials containing PBA. When glucose molecules bind to the surface of photonic crystals, it can cause changes in the optical properties of the photonic crystal, such as changes in refractive index. By measuring the changes in optical properties, it is possible to detect glucose concentration. Photonic crystal sensors have the advantages of fast response speed, high sensitivity, and easy integration.

Electrochemical sensor:Electrochemical sensors are sensors that convert changes in current or potential generated by biochemical reactions into measurable signals. Due to its high affinity for carbohydrate molecules, it is often used as a recognition element in electrochemical sensors.

Gel sensor:Gel sensor is a kind of sensor that uses the volume or shape change of gel material to detect the analyte. PBA can be used as recognition element of gel sensor because of its high binding force with carbohydrate molecules.

Amide hydrogel sensor:The amide hydrogel sensor can be prepared by synthesizing acrylamide copolymer containing PBA. When the hydrogel is combined with glucose or other sugars, the volume of the gel will change (such as expansion or contraction). This volume change can be converted into electrical signals or other measurable signals, thereby achieving the detection of sugar concentration. The amide hydrogel sensor has the advantages of fast response, high sensitivity and good selectivity.

In summary, PBA, with its high affinity for sugars and biomolecules, serves as a versatile recognition element in various sensors. These include fluorescent, electrochemical, photonic crystal, and gel sensors, which achieve high sensitivity and selectivity in detecting glucose, hydrogen peroxide, and other analytes. They provide reliable technical support for biochemical and clinical detection, laying a foundation for the development of advanced sensing devices.

Then, a fluorescence quencher was synthesized using PBA and bipyridine as raw materials. When glucose is added to the system, PBA combines with glucose to form tetrahedral anionic boronic esters, effectively neutralizing the positive charge of the fluorescence quencher and restoring the fluorescence of GQDs. By measuring changes in fluorescence intensity, quantitative detection of glucose concentration can be achieved.

Application Direction

Biomedical field

 

In the field of biomedicine, 1,4-Phenylenebisboronic acid biosensors can be used to monitor glucose concentration in organisms, detect cancer markers, and more. For example, by building a glucose sensor based on PBA, the blood glucose level of diabetes patients can be monitored in real time, providing strong support for the treatment and management of diabetes. 

Environmental monitoring field

 

In the field of environmental monitoring, PBA biosensors can be used to detect pollutants in water bodies, monitor air quality, and more. For example, by constructing PBA based electrochemical sensors, it is possible to detect heavy metal ions, organic pollutants, etc. in water bodies. In addition, the binding ability of PBA with carbohydrate molecules can be utilized to develop biosensors.

Food hygiene field

 

In the field of food hygiene, PBA biosensors can be used to detect additives, sugar content, and other substances in food. For example, by constructing fluorescence sensors or electrochemical sensors based on PBA, rapid detection of sugars such as glucose and fructose in food can be achieved. In addition, the binding ability of PBA with specific additives can be utilized to develop biosensors.

1,4-Phenyldiboronic acid, as a novel carbohydrate recognition molecule, has shown great potential in the field of biosensors. By combining them with sensing technologies such as electrochemistry, fluorescence, gel and photonic crystals, different types of biosensors can be constructed to achieve high sensitivity and selectivity for the detection of sugar molecules and other biological molecules.

 

Structurally, 1,4-phenylenebisboronic acid showcases a benzene ring as its core scaffold. Positioned at the 1 and 4 positions of this aromatic ring are two boronic acid groups, denoted as -B(OH)2. This specific arrangement contributes to the compound's unique molecular geometry and distinct chemical properties.The boronic acid functionalities (-B(OH)2) are known for their ability to engage in reversible covalent bonding.

 

Particularly under mild reaction conditions. This characteristic is crucial in synthetic chemistry, as it allows for the formation of stable, yet labile, intermediates and products. The reversibility of these boronate ester bonds is particularly advantageous, as it provides a means for controlling the structure and properties of synthetic molecules through carefully designed reaction conditions.

 

Furthermore, the aromatic nature of the benzene ring imparts stability and planarity to the molecule, which can influence its intermolecular interactions and solubility properties. The presence of two boronic acid groups also enhances the compound's potential for multivalent interactions, a feature that is exploited in the design of supramolecular assemblie.

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