Naphthoquinone and Benzoquinone Dyes

A large number of naphthoquinone and benzoquinone dyes occur naturally as plant constituents, and in the past many of these have found use as colorants. The chemistry of synthetic analogues began with the discovery of naphthazarin (1) [475-38-7] by Roussin in 1861. Naphthazarin and its derivatives first found use as black chrome mordant dyes for wool and silk. In contrast to the naphthoquinones, synthetic benzoquinone dyes are few in number and are generally of the 

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Naphthoquinone Derivatives, These dyes are generally not very colorfast and sometimes also fade. Anthraquinone derivatives have better properties (see Dyes, ANTHRAQUINONE). New developments are based on compounds that combine the chemical structure of phenothiazine or phenoselenazine derivatives with benzoquinone or naphthoquinone units (16). These dyes show good chemical stability. Naphthoquinone derivatives have yet to find a practical application as dyes in WORM disks because of the high expenditure for synthesis due to low yields. 

In the case of the naphthoquinone methine-type near-IR dye 55, reduction with tin(II) chloride under acidic conditions gives the leuco dye 56, which has weak absorption maxima at 350-359nm in methanol. The leuco dye 56 can be isolated as a stable pale yellow compound. The oxidation behavior of 56 has been studied by adding benzoquinone as oxidant in methanol solution. Compound 56 immediately produced new absorption at 760 nm which is consistent with the absorption maximum of 55 (Scheme 19).30 The absorption spectra of the leuco, quinone, and metal complex forms are summarized in Table 3. 

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