triarylmethane dye
{{short description|Class of dye}}
Triarylmethane dyes are synthetic organic compounds containing triphenylmethane backbones. As dyes, these compounds are intensely colored. They are produced industrially as dyes.{{Ullmann's | last1 = Gessner | first1 = Thomas | last2 = Mayer | first2 = Udo | title = Triarylmethane and Diarylmethane Dyes | year = 2000 | doi = 10.1002/14356007.a27_179}}
Families
Triarylmethane dyes can be grouped into families according to the nature of the substituents on the aryl groups. In some cases, the anions associated with the cationic dyes (say crystal violet) vary even though the name of the dye does not. Often it is shown as chloride.
=Methyl violet dyes=
Methyl violet dyes have dimethylamino groups at the p-positions of two aryl groups.
Image:Methyl Violet 2B.svg|Methyl violet 2B
Image:Methyl Violet 6B.svg|Methyl violet 6B
Image:Kristallviolett.svg|Methyl violet 10B
=Fuchsine dyes=
Fuchsine dyes have primary or secondary amines (NH2 or NHMe) functional groups at the p-positions of each aryl group.
File:Pararosaniline.png|Pararosaniline
File:Rosaniline hydrochloride.svg|Fuchsine (hydrochloride salt)
Neofuchsin.svg|New fuchsine (As chloride)
Fuchsine acid vector.svg|Fuchsine acid
=Phenol dyes=
Phenol dyes have hydroxyl groups at the p positions of at least two aryl groups.
File:Phenolphthalein-low-pH-2D-skeletal.svg|Phenolphthalein
File:Phenol-red-zwitterionic-form-2D-skeletal.png|Phenol red
File:Chlorophenol red.png|Chlorophenol red
File:Cresol Red.svg|Cresol red
File:Bromocresol purple.svg|Bromocresol purple
File:Bromocresol green.svg|Bromocresol green
=Malachite green dyes=
Malachite green dyes are related to the methyl violet dyes, except that they contain one phenyl (C6H5) group.
Image:Malachite green structure.svg |Malachite green
Image:Structure of the dye brilliant green.png|Brilliant green (dye)
Image:Brilliant Blue FCF(2).svg|Brilliant blue FCF, a common food colorant
=Victoria blue dyes=
Victoria blue dyes are related to the methyl violet dyes, except they contain one naphthylamino group. Variation is found is dimethylamine vs diethylamino substituents on the phenyl rings and variations of the secondary amine on the naphthyl group.
File:Victoria blue B with charge.svg|Victoria blue B
File:Victoria blue FBR revised.svg |Victoria blue FBR
File:Victoria blue BO.svg|Victoria blue BO
File:Victoria pure blue FGA revised.svg|Victoria blue FGA
File:Victoria blue 4 R revised.svg|Victoria blue 4 R
File:Victoria blue R revised.svg|Victoria blue R
=Xanthene dyes=
{{see also|fluoran}}
Xanthene dyes feature a xanthene core. They are not widely used as textiles, but for other applications.
File:EosinB.png|Eosin B
File:EosinY.png|Eosin Y
File:rhodamine B.svg|Rhodamine B
File:Rhodamine 123.svg|Rhodamine 123
File:Fluorescein 2.svg |Fluorescein
Bridged arenes
Where two of the aryl groups are bridged by a heteroatom, these triarylmethane compounds may be further categorized into acridines (nitrogen-bridged), xanthenes (oxygen-bridged), and thioxanthenes (sulfur-bridged).
Synthesis
The amine-containing dyes are often prepared from Michler's ketone or its diethylamino analogue. In this way, the third aryl group is readily differentiated. The Friedel–Crafts alkylation reaction is a popular method to prepare many of the phenolic derivatives:
Applications
In addition to their dominant use as dyes, many of these dyes react reversibly with acid and base, and thus serve as pH indicators.
