Crystal violet lactone (CVL) is a

leuco dye A leuco dye (from the Greek λευκός ''leukos'': white ) is a dye which can switch between two chemical forms; one of which is colorless. Reversible transformations can be caused by heat, light or pH; resulting in examples of thermochromism, ...

, a

lactone Lactones are cyclic carboxylic esters, containing a 1-oxacycloalkan-2-one structure (), or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. Lactones are formed by intramolecular esterification of the co ...

derivate of

crystal violet Crystal violet or gentian violet, also known as methyl violet 10B or hexamethyl pararosaniline chloride, is a triarylmethane dye used as a histological stain and in Gram's method of classifying bacteria. Crystal violet has antibacterial, antif ...

10B. In pure state it is a slightly yellowish crystalline powder, soluble in nonpolar or slightly polar

organic solvent A solvent (s) (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for p ...

s. The central carbon in the leuco form is in a

tetrahedral In geometry, a tetrahedron (plural: tetrahedra or tetrahedrons), also known as a triangular pyramid, is a polyhedron composed of four triangular faces, six straight edges, and four vertex corners. The tetrahedron is the simplest of all the ...

configuration, with four

covalent bond A covalent bond is a chemical bond that involves the sharing of electrons to form electron pairs between atoms. These electron pairs are known as shared pairs or bonding pairs. The stable balance of attractive and repulsive forces between atoms ...

s. In an acidic environment, the

ring is broken, with the oxygen detaching from the central carbon. This now-trivalent position is a planar

carbocation A carbocation is an ion with a positively charged carbon atom. Among the simplest examples are the methenium , methanium and vinyl cations. Occasionally, carbocations that bear more than one positively charged carbon atom are also encountere ...

that is

resonance stabilized In chemistry, resonance, also called mesomerism, is a way of describing bonding in certain molecules or polyatomic ions by the combination of several contributing structures (or ''forms'', also variously known as ''resonance structures'' or ...

, interconnecting the π systems of the

aromatic ring 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 saturat ...

s and the

amino In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituent ...

functional group In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the rest ...

s. This single large

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 as ...

is a chromophore with strong absorption in

visible spectrum The visible spectrum is the portion of the electromagnetic spectrum that is visual perception, visible to the human eye. Electromagnetic radiation in this range of wavelengths is called ''visible light'' or simply light. A typical human eye wil ...

, giving this compound its distinctive color. This chemical is usually drawn in the

resonance structure In chemistry, resonance, also called mesomerism, is a way of describing bonding in certain molecules or polyatomic ions by the combination of several contributing structures (or ''forms'', also variously known as ''resonance structures'' or '' ...

with the cation on nitrogen. : It was the first dye used in

carbonless copy paper Carbonless copy paper (CCP), non-carbon copy paper, or NCR paper (No Carbon Required, taken from the initials of its creator, National Cash Register) is a type of coated paper designed to transfer information written on the front onto sheets beneat ...

s, and it is still widely used in this application. It is also the

component in some

thermochromic Thermochromism is the property of substances to change color due to a change in temperature. A mood ring is an excellent example of this phenomenon, but thermochromism also has more practical uses, such as baby bottles which change to a differen ...

dyes, e.g. in the

Hypercolor Hypercolor was a line of clothing, mainly T-shirts and shorts, that changed color with heat. They were manufactured by Generra Sportswear Company of Seattle and marketed in the United States as Generra Hypercolor or Generra Hypergrafix and el ...

line of clothing. One of its novel uses is a security marker for fuels. Its limitations as a fuel marker have to be carefully contemplated by users, as Crystal Violet Lactone (leuco) readily transforms to the colored species in >10% Ethanol Containing Gasoline, imparting a strong color. Crystal violet lactone as a fuel marker was covered by the

BASF BASF Societas Europaea, SE () is a German multinational corporation, multinational chemical company and the List of largest chemical producers, largest chemical producer in the world. Its headquarters is located in Ludwigshafen, Germany. The ...

patent DE4422336A1 until June 2014. It may cause allergic

contact dermatitis Contact dermatitis is a type of acute or chronic inflammation of the skin caused by exposure to chemical or physical agents. Symptoms of contact dermatitis can include itchy or dry skin, a red rash, bumps, blisters, or swelling. These rashes are ...

in people handling the carbonless copy paper.

References

{{reflist Triarylmethane dyes Anilines