Phenoxazine is a

heterocyclic compound A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). Heterocyclic chemistry is the branch of organic chemistry dealing with the synthesis, properties, and ...

. The structure of phenoxazine consists of an

oxazine Oxazines are heterocyclic compounds containing one oxygen and one nitrogen atom in a doubly unsaturated six-membered ring. Isomers exist depending on the relative position of the heteroatoms and relative position of the double bonds. By extensi ...

fused to two

benzene Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, ...

rings. It occurs as the central core of a number of naturally occurring chemical compounds such as

dactinomycin Dactinomycin, also known as actinomycin D, is a chemotherapy medication used to treat a number of types of cancer. This includes Wilms tumor, rhabdomyosarcoma, Ewing's sarcoma, trophoblastic neoplasm, testicular cancer, and certain types of ovari ...

and

litmus Litmus is a water-soluble mixture of different dyes extracted from lichens. It is often absorbed onto filter paper to produce one of the oldest forms of pH indicator, used to test materials for acidity. It is a purple dye that is extracted fro ...

. The dyes Nile blue and

Nile red The Nile, , Bohairic , lg, Kiira , Nobiin: Áman Dawū is a major north-flowing river in northeastern Africa. It flows into the Mediterranean Sea. The Nile is the longest river in Africa and has historically been considered the longest rive ...

are also based on a phenoxazine core. Phenoxazine dyes were once widely used for silk dyeing, but due to their lack of

lightfastness Lightfastness is a property of a colourant such as dye or pigment that describes its resistance to fading when exposed to light. Dyes and pigments are used for example for dyeing of fabrics, plastics or other materials and manufacturing paints or ...

they have disappeared over time from the market. However, since their light resistance is significantly better on

acrylic fiber Acrylic fibers are synthetic fibers made from a polymer (polyacrylonitrile) with an average molecular weight of ~100,000, about 1900 monomer units. For a fiber to be called "acrylic" in the US, the polymer must contain at least 85% acrylonitr ...

s, these dyes have experienced a renaissance.

References

{{heterocyclic-stub

See also

References