1,1-Azobis-1,2,3-triazole is a moderately explosive but comparatively stable

chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...

which contains a long continuous chain of

nitrogen Nitrogen is the chemical element with the symbol N and atomic number 7. Nitrogen is a nonmetal and the lightest member of group 15 of the periodic table, often called the pnictogens. It is a common element in the universe, estimated at se ...

atoms, with an unbroken chain of eight nitrogen atoms cyclised into two 1,2,3-triazole rings. It is stable up to 194 °C. The compound exhibits

cis–trans isomerism ''Cis''–''trans'' isomerism, also known as geometric isomerism or configurational isomerism, is a term used in chemistry that concerns the spatial arrangement of atoms within molecules. The prefixes "''cis''" and "''trans''" are from Latin: " ...

at the central

azo group Azo compounds are organic compounds bearing the functional group diazenyl (, in which R and R′ can be either aryl or alkyl groups). IUPAC defines azo compounds as: "Derivatives of diazene (diimide), , wherein both hydrogens are substituted ...

: the ''trans'' isomer is more stable and is yellow, while the ''cis'' isomer is less stable and is blue. The two rings are

aromatic In chemistry, aromaticity is a chemical property of cyclic ( ring-shaped), ''typically'' planar (flat) molecular structures with pi bonds in resonance (those containing delocalized electrons) that gives increased stability compared to satur ...

and form a

conjugated system In theoretical chemistry, a conjugated system is a system of connected p-orbitals with delocalized electrons in a molecule, which in general lowers the overall energy of the molecule and increases stability. It is conventionally represented ...

with the azo linkage. This

chromophore A chromophore is the part of a molecule responsible for its color. The color that is seen by our eyes is the one not absorbed by the reflecting object within a certain wavelength spectrum of visible light. The chromophore is a region in the mo ...

allows the ''trans'' compound to be

isomer In chemistry, isomers are molecules or polyatomic ions with identical molecular formulae – that is, same number of atoms of each element – but distinct arrangements of atoms in space. Isomerism is existence or possibility of isomers. Is ...

ised to the ''cis'' when treated with an appropriate wavelength of

ultraviolet Ultraviolet (UV) is a form of electromagnetic radiation with wavelength from 10 nm (with a corresponding frequency around 30 PHz) to 400 nm (750 THz), shorter than that of visible light, but longer than X-rays. UV radiation ...

light.

Related compounds

In 2011, azobis(tetrazole) was prepared by Klapötke and Piercey which has a ten-nitrogen chain. The record was later taken by a N11 chain compound synthesized by a group of Chinese researchers. A branched chain N11 system has also been reported as part of an unstable but highly nitrogen rich azidotetrazole derivative with formula CN.

References

{{DEFAULTSORT:Azobis-1, 2, 3-triazole, 1, 1'- Explosive chemicals Triazoles

Related compounds

See also

References