Crystal violet lactone

Last updated
Reversible photochromism of a crystal violet lactone salicylaldehyde hydrazone Zn(II) complex dissolved in dichloromethane Crystal violet lactone photochromism.jpg
Reversible photochromism of a crystal violet lactone salicylaldehyde hydrazone Zn(II) complex dissolved in dichloromethane

Crystal violet lactone (CVL) is a leuco dye, a lactone derivate of crystal violet 10B. In pure state it is a slightly yellowish crystalline powder, soluble in nonpolar or slightly polar organic solvents.

The central carbon in the leuco form is in a tetrahedral configuration, with four covalent bonds. In an acidic environment, the lactone ring is broken, with the oxygen detaching from the central carbon. This now-trivalent position is a planar carbocation that is resonance stabilized, interconnecting the π systems of the aromatic rings and the amino functional groups. This single large conjugated system is a chromophore with strong absorption in visible spectrum, giving this compound its distinctive color. This chemical is usually drawn in the resonance structure with the cation on nitrogen.

Transformation between leuco and colored form of crystal violet lactone, halochromism Crystal violet lactone reaction.svg
Transformation between leuco and colored form of crystal violet lactone, halochromism

It was the first dye used in carbonless copy papers, and it is still widely used in this application. It is also the leuco dye component in some thermochromic dyes, e.g. in the Hypercolor 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 patent DE4422336A1 until June 2014. [1]

It may cause allergic contact dermatitis in people handling the carbonless copy paper.

Related Research Articles

<span class="mw-page-title-main">Conjugated system</span> System of connected p-orbitals with delocalized electrons in a molecule

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 having alternating single and multiple bonds. Lone pairs, radicals or carbenium ions may be part of the system, which may be cyclic, acyclic, linear or mixed. The term "conjugated" was coined in 1899 by the German chemist Johannes Thiele.

<span class="mw-page-title-main">Carbon paper</span> Paper used to make copies

Carbon paper consists of sheets of paper that create one or more copies simultaneously with the creation of an original document when inscribed by a typewriter or ballpoint pen. The email term cc which means ‘carbon copy’ is derived from carbon paper.

<span class="mw-page-title-main">Hypercolor</span> Clothing brand that changes color

Hypercolor was a line of clothing, mainly T-shirts and shorts, that changed color with heat.

<span class="mw-page-title-main">Carbonless copy paper</span> Coated paper used for copying

Carbonless copy paper (CCP), non-carbon copy paper, or NCR paper is a type of coated paper designed to transfer information written on the front onto sheets beneath. It was developed by chemists Lowell Schleicher and Barry Green, as an alternative to carbon paper and is sometimes misidentified as such.

<span class="mw-page-title-main">Fuchsine</span> Chemical compound

Fuchsine (sometimes spelled fuchsin) or rosaniline hydrochloride is a magenta dye with chemical formula C20H19N3·HCl. There are other similar chemical formulations of products sold as fuchsine, and several dozen other synonyms of this molecule.

<span class="mw-page-title-main">Crystal violet</span> Triarylmethane dye used as a histological stain and in Grams method of classifying bacteria

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, antifungal, and anthelmintic (vermicide) properties and was formerly important as a topical antiseptic. The medical use of the dye has been largely superseded by more modern drugs, although it is still listed by the World Health Organization.

<span class="mw-page-title-main">Thermochromism</span> Property of substances to change colour due to a change in temperature

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 different color when cool enough to drink, or kettles which change color when water is at or near boiling point. Thermochromism is one of several types of chromism.

Thermochromic ink is a type of dye that changes color in response to a change in temperature. It was first used in the 1970s in novelty toys like mood rings, but has found some practical uses in things such as thermometers, product packaging, and pens. The ink has also found applications within the medical field for specific medical simulations in medical training. Thermochromic ink can also turn transparent when heat is applied; an example of this type of ink can be found on the corners of an examination mark sheet to prove that the sheet has not been edited or photocopied.

<span class="mw-page-title-main">Schiff test</span> Organic chemistry named reaction

The Schiff test is an early organic chemistry named reaction developed by Hugo Schiff, and is a relatively general chemical test for detection of many organic aldehydes that has also found use in the staining of biological tissues. The Schiff reagent is the reaction product of a dye formulation such as fuchsin and sodium bisulfite; pararosaniline and new fuchsin are not dye alternatives with comparable detection chemistry.

Vat dyes are a class of dyes that are classified as such because of the method by which they are applied. Vat dyeing is a process that refers to dyeing that takes place in a bucket or vat. The original vat dye is indigo, once obtained only from plants but now often produced synthetically.

LCV can stand for:

<span class="mw-page-title-main">Leuco dye</span>

A leuco dye 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, photochromism and halochromism, respectively. Irreversible transformations typically involve reduction or oxidation. The colorless form is sometimes referred to as the leuco form.

Zubbles is a commercial name for colored soap bubbles. Zubbles claim to fame is that they are the first colored soap bubbles that do not leave stains. Instead they fade away with exposure to air, pressure, and water.

<span class="mw-page-title-main">Fuel dye</span> Dyes added to identify fuels

Fuel dyes are dyes added to fuels, as in some countries it is required by law to dye a low-tax fuel to deter its use in applications intended for higher-taxed ones. Untaxed fuels are referred to as "dyed", while taxed ones are called "clear" or "white".

<span class="mw-page-title-main">Thionine</span> Chemical compound and histologic stain C12H10N3S

Thionine, also known as Lauth's violet, is the salt of a heterocyclic compound. It was firstly synthesised by Charles Lauth. A variety of salts are known including the chloride and acetate, called respectively thionine chloride and thionine acetate. The dye is structurally related to methylene blue, which also features a phenothiazine core. The dye's name is frequently misspelled with omission of the e, and is not to be confused with the plant protein thionin. The -ine ending indicates that the compound is an amine.

<span class="mw-page-title-main">Triphenylmethanol</span> Chemical compound

Triphenylmethanol is an organic compound. It is a white crystalline solid that is insoluble in water and petroleum ether, but well soluble in ethanol, diethyl ether, and benzene. In strongly acidic solutions, it produces an intensely yellow color, due to the formation of a stable "trityl" carbocation. Many derivatives of triphenylmethanol are important dyes.

<span class="mw-page-title-main">Thermal paper</span> Adding machine, cash register and credit card terminal paper

Thermal paper is a special fine paper that is coated with a material formulated to change color locally when exposed to heat. It is used in thermal printers, particularly in inexpensive devices such as adding machines, cash registers, and credit card terminals and small, lightweight portable printers.

<span class="mw-page-title-main">Azo violet</span> Chemical compound

Azo violet (Magneson I; p-nitrobenzeneazoresorcinol) is an azo compound with the chemical formula C12H9N3O4. It is used commercially as a violet dye and experimentally as a pH indicator, appearing yellow below pH 11, and violet above pH 13. It also turns deep blue in the presence of magnesium salt in a slightly alkaline, or basic, environment. Azo violet may also be used to test for the presence of ammonium ions. The color of ammonium chloride or ammonium hydroxide solution will vary depending upon the concentration of azo violet used. Magneson I is used to test Be also; it produces an orange-red lake with Be(II) in alkaline medium.

Methine dyes are dyes whose chromophoric system consists of conjugated double bonds (polyenes) flanked by two end groups: an electron acceptor A and an electron donor D.


Structural of methine dyes

Polycarbonyl, is a solid, metastable, and explosive polymer of carbon monoxide. The polymer is produced by exposing carbon monoxide to high pressures. The structure of the solid appears amorphous, but may include a zigzag of equally-spaced CO groups.

References

  1. Schloesser, Ulrike; et al. (1994). "Using Leukotriarylmethanen for marking hydrocarbons".