(E)-5,5′-(Diazene-1,2-diyl)diisophthalic Acid (CAS 365549-33-3): Multifunctional Organic Building Block — Full Analysis of Molecular Structure, MOF Synthesis, Photoresponsive Properties and Advanced Material Applications

1、 Product Overview

(E)-5,5′-(Diazene-1,2-diyl)diisophthalic acid, also known as 3,3′,5,5′-azobenzenetetracarboxylic acid or TAZBH₄, is a multifunctional aromatic carboxylic acid containing an azobenzene core and four carboxylic acid groups. Its rigid conjugated structure, multiple coordination sites, and photoresponsive azo functionality make it a valuable organic building block for advanced materials research. Its greatest value lies in its ability to serve as a multifunctional linker for metal-organic frameworks (MOFs), coordination polymers, porous materials, and other functional organic-inorganic hybrid systems. The combination of tetracarboxylic acid functionality and an azobenzene unit also makes it particularly attractive for research into photoresponsive materials, molecular switching, adsorption and separation, and stimuli-responsive porous structures.

2. Basic Product Information

1. Product Name: (E)-5,5′-(Diazene-1,2-diyl)diisophthalic acid

2. Synonyms: 3,3′,5,5′-Azobenzenetetracarboxylic acid; TAZBH₄; Bis(3,5-dicarboxyphenyl)diazene; 3,5,3′,5′-Azobenzenetetracarboxylic acid

3. CAS NO.: 365549-33-3

4. Molecular Formula: C₁₆H₁₀N₂O₈

5. Molecular Weight: 358.26 g/mol

6. Structural Formula:

6. Purity: ≥ 97%

7. Appearance: White or almost white crystalline powder

8. Functional Groups: Four carboxylic acid groups and one azobenzene (-N=N-) linkage

9. Chemical Classification: Aromatic carboxylic acid; azo compound; multifunctional organic linker; specialty chemical building block

10. Main Applications: MOF synthesis; coordination polymers; porous materials; photoresponsive materials; molecular switching; gas adsorption and separation research; advanced functional materials

11. Storage Conditions: Store in a cool, dry and dark environment at room temperature. Keep the container tightly closed and protect from moisture and prolonged exposure to light.

12. Product Manager Email: selina@coreychem.com

3、 Frequently Asked Questions (FAQ)

Question 1: What are the basic physical properties of (E)-5,5′-(diazene-1,2-diyl)diisophthalic acid (CAS NO.: 365549-33-3)?

This product is an aromatic azo compound containing four carboxylic acid groups. It is generally supplied as a white to light-colored crystalline powder. Its molecular formula is C₁₆H₁₀N₂O₈, with a molecular weight of 358.26 g/mol. The product is typically handled as a specialty organic acid and should be stored in a tightly closed container in a cool, dry place, protected from excessive heat and moisture.

Question 2:What are the common synthesis methods for this compound?

1. Azo coupling of aromatic precursors:
A common synthetic strategy involves preparing appropriately substituted aromatic amine or nitro/carboxylic acid intermediates, followed by formation of the azo (-N=N-) linkage under controlled reaction conditions. The carboxylic acid groups are retained or introduced during the synthesis to obtain the final azobenzene tetracarboxylic acid structure.
2. Oxidative or stepwise synthesis from substituted azobenzene intermediates:
Another approach is to first construct the azobenzene core and subsequently introduce or convert functional groups into carboxylic acid groups. Careful control of oxidation conditions and purification is required because the molecule contains multiple carboxyl groups and an azo linkage.

For commercial production, the synthetic route needs to be optimized according to the required purity, batch size, and impurity profile.

Question 3:What is the main feature of this product in terms of application?

Its main application feature is its combination of a rigid azobenzene core with four carboxylic acid functional groups. This structure provides multiple coordination sites and makes the compound useful as an organic building block for advanced functional materials.

It is particularly valuable in the preparation of metal-organic frameworks (MOFs), coordination polymers, porous materials, and other functional organic materials. The azo group can also provide photoresponsive properties, making this type of compound of interest for research involving molecular switching, light-responsive materials, and functional porous structures.

Question 4:What is the solubility and stability of this product in different solvents? Can it be used in aqueous systems?

Because the molecule contains four carboxylic acid groups and a rigid aromatic structure, its solubility depends strongly on the solvent and pH. It is expected to have limited solubility in many common organic solvents, while its solubility can be improved in aqueous systems under conditions where the carboxylic acid groups are partially or fully ionized.

The product should generally be handled under controlled conditions and protected from prolonged exposure to strong acids, strong bases, excessive heat, and intense light. For specific applications, especially aqueous or photoresponsive systems, the actual solubility and stability should be evaluated under the intended operating conditions.

Question 5:Is this product suitable as a building block for MOFs and coordination polymers? What are the considerations?

Yes. The four carboxylic acid groups make this compound a promising multidentate organic linker for the preparation of MOFs and coordination polymers. The multiple carboxylate groups can coordinate with metal ions to form extended one-, two-, or three-dimensional structures, depending on the metal center and synthesis conditions.

The azo group may additionally introduce useful photoresponsive or electronic properties into the resulting material. When used for MOF or coordination-polymer synthesis, important considerations include purity, positional isomer content, residual inorganic impurities, moisture content, particle properties, and the reproducibility of the linker structure. High-purity material is generally preferred for structural and functional materials research.

4、 Application Cases

Application 1: What is the role of (E)-5,5′-(diazene-1,2-diyl)diisophthalic acid (CAS NO.: 365549-33-3) in the field of MOF and coordination chemistry?

(E)-5,5′-(Diazene-1,2-diyl)diisophthalic acid is a multifunctional aromatic dicarboxylic acid derivative containing an azobenzene core and four carboxylic acid groups. The multiple carboxyl groups can act as coordination sites for metal ions, making the compound a valuable organic linker for the construction of metal-organic frameworks (MOFs) and coordination polymers. Its rigid molecular structure can contribute to the formation of extended porous architectures with tunable structural and chemical properties. In research, it can be used to investigate the relationship between linker structure, metal coordination, framework topology, and porosity, particularly in the development of advanced functional porous materials.

Application 2: What is the role of the product in the field of photoresponsive and light-responsive materials?

The azobenzene unit in (E)-5,5′-(diazene-1,2-diyl)diisophthalic acid provides an important photoresponsive structural feature. Azobenzene groups can undergo reversible trans-cis photoisomerization under appropriate irradiation conditions, resulting in changes in molecular geometry and polarity. When incorporated into coordination frameworks or other functional materials, this structural switching can potentially be translated into changes in pore environment, molecular recognition, adsorption behavior, or other physicochemical properties. Therefore, the product is of interest for research into photoresponsive materials, molecular switches, light-controlled molecular systems, and stimuli-responsive porous materials.

Application 3: What is the role of the product in the field of porous materials and gas adsorption?

The combination of a rigid aromatic backbone and multiple carboxylic acid groups makes this compound a useful building block for designing porous coordination materials. When coordinated with suitable metal centers, it can contribute to the formation of highly ordered porous structures with accessible internal surfaces. Such materials can be investigated for the adsorption and separation of gases and other small molecules. Research applications may include the development of materials for gas storage, molecular sieving, selective adsorption, and separation processes. The azo functionality can additionally provide a route toward externally controlled or stimuli-responsive adsorption behavior.

Application 4: What is the role of the product in the field of functional and advanced materials research?

(E)-5,5′-(Diazene-1,2-diyl)diisophthalic acid is an attractive multifunctional building block for advanced materials because it combines multiple carboxylic acid groups with a conjugated azo aromatic structure. The carboxyl groups provide opportunities for coordination and supramolecular interactions, while the azo group can contribute photoresponsive and electronic properties. This combination makes the product suitable for research into coordination polymers, supramolecular assemblies, functional organic materials, and hybrid organic-inorganic materials. It can also be used to explore how molecular structure and functional groups influence the mechanical, optical, electronic, and adsorption properties of the resulting materials.

Application 5: What is the role of the product in the field of chemical and materials research?

The product serves as a specialized organic building block for researchers developing new functional molecules and materials. Its well-defined tetracarboxylic acid functionality allows it to participate in esterification, coordination, and other derivatization reactions, while the azobenzene moiety provides an additional functional handle for designing stimuli-responsive systems. It can therefore be used in laboratory-scale research to synthesize novel organic linkers, coordination complexes, porous frameworks, and photoactive materials. Its high-purity grade is particularly useful when reproducible structural and material-property studies are required.

5、 Safety and Storage

1. Store in a cool, dry, and well-ventilated area and keep the container tightly sealed.

2. Protect from moisture and prolonged exposure to light. Store at room temperature under dry conditions. For long-term storage, refrigeration at 2-8°C may be considered.

3. Keep away from strong oxidizers, strong acids, and strong bases to avoid potential decomposition or undesired reactions.

4. Handle with standard laboratory precautions. Wear appropriate personal protective equipment (PPE), including protective gloves, safety goggles, and a lab coat. Avoid generating and inhaling dust.

5. In case of contact with skin or eyes, rinse immediately with plenty of water. If irritation or discomfort persists, seek medical attention.

6、Product Manager Information

Product Manager: Selina
Email: selina@coreychem.com