Azobenzene

0.001,365.00

Azobenzene is a chemical compound composed of two phenyl rings connected by a nitrogen double bond (N=N), exhibiting cis-trans isomerism. It’s known for its photoswitching properties, where light irradiation can reversibly change its molecular shape.

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Azobenzene is an intriguing chemical compound with unique properties, primarily its ability to undergo reversible structural changes when exposed to light. Here's a more detailed description:

Key Characteristics and Structure:

  • Chemical Structure:
    • It consists of two phenyl rings (benzene rings) linked by a nitrogen double bond (N=N). This nitrogen double bond is the key to its unique properties.
    • The chemical formula is C₁₂H₁₀N₂.
  • Isomerism:
    • Azobenzene exhibits cis-trans isomerism. This means it can exist in two different geometric forms:
      • trans-azobenzene: The more stable form, where the phenyl rings are on opposite sides of the N=N bond.
      • cis-azobenzene: The less stable form, where the phenyl rings are on the same side of the N=N bond.
  • Photoswitching:
    • The most notable property of azobenzene is its ability to switch between the cis and trans isomers when exposed to light.
    • UV light can convert trans-azobenzene to cis-azobenzene.
    • Visible light or heat can convert cis-azobenzene back to trans-azobenzene.

Applications and Significance:

  • Photoswitchable Materials:
    • Azobenzene's photoswitching properties make it valuable in developing photoswitchable materials. These materials can change their properties (e.g., shape, color, solubility) in response to light.
  • Molecular Switches:
    • It's used in molecular switches, which are molecules that can change their conformation in response to external stimuli. These have applications in areas like data storage and molecular electronics.
  • Drug Delivery:
    • Azobenzene derivatives are being explored for use in drug delivery systems, where light can be used to control the release of drugs.
  • Materials Science:
    • It's used in the development of photoresponsive polymers and other materials with light-controlled properties.
  • Research:
    • Azobenzene is a very important compound in the study of photochromic materials.

Important Considerations:

  • The photoswitching process is reversible and can be repeated many times.
  • The specific wavelengths of light required for the cis-to-trans and trans-to-cis conversions depend on the substituents attached to the azobenzene molecule.

In essence, azobenzene's ability to change its shape with light makes it a versatile compound with applications in various fields, particularly in materials science and nanotechnology.

Additional information

Weight N/A
CAS number

103-33-3

Chemical formula

C₁₂H₁₀N₂

Molar mass

182.226 g/mol

Physical state

Orange-red crystals.

Odor

Weak odor.

Melting point

trans-isomer: 67.88 °C

Boiling point

Approximately 300 °C.

Density

1.203 g/cm³

Solubility in water

Very low solubility (6.4 mg/L at 25 °C).

Flash point:

476 °C.

Autoignition temperature

NA

Dye Content

Azobenzene is related to azo dyes, and is a chromophore, that contributes to the color of many dyes.

Vapor pressure

NA

UN number

NA

Flammability

Combustible

Carcinogenicity

There are concerns regarding the toxicity of azobenzene, and some of it's related compounds are considered carcinogenic. There are hazard statements regarding it's potential carcinogenic effects.

Grade

CP

Size

50 gm, 500 gm, 5 kg

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