azobenzene
Sign in to saveAzobenzene is a photoswitchable chemical compound composed of two phenyl rings linked by a N=N double bond. It is the simplest example of an aryl azo compound. The term "azobenzene" or simply "azo" is often used to refer to a wide class of similar compounds. These azo compounds are considered as derivatives of diazene (diimide), and are sometimes referred to as "diazenes". The diazenes absorb light strongly and are common dyes. Different classes of azo dyes exist, most notably the ones substituted with heteroaryl rings.
Article
10 sectionsContents
- Structure and synthesis
- Reactions
- Trans–cis isomerization
- Spectroscopic classification
- Photophysics of isomerization
- Photoinduced motions
- Miscellaneous
- References
- Cited sources
- Further reading
Azobenzene is a photoswitchable chemical compound composed of two phenyl rings linked by a N=N double bond. It is the simplest example of an aryl azo compound. The term "azobenzene" or simply "azo" is often used to refer to a wide class of similar compounds. These azo compounds are considered as derivatives of diazene (diimide), and are sometimes referred to as "diazenes". The diazenes absorb light strongly and are common dyes. Different classes of azo dyes exist, most notably the ones substituted with heteroaryl rings.
==Structure and synthesis== thumb|left|upright|X-ray crystallography reveals the highly nonplanar, twisted structure for cis-azobenzene. Azobenzene was first described by Eilhard Mitscherlich in 1834. Yellowish-red crystalline flakes of azobenzene were obtained in 1856. Its original preparation is similar to the modern one. According to the 1856 method, nitrobenzene is reduced by iron filings in the presence of acetic acid. In the modern synthesis, zinc is the reductant in the presence of a base. Industrial electrosynthesis using nitrobenzene is also employed.