Chemistry of Triphenylmethane

Session Objectives

By the end of this session, students will be able to:

Ø  Discuss the chemistry, reactivity, properties and methods of synthesis of Phenanthrene

Chemistry of Triphenylmethane

•       Triphenylmethane, or triphenyl methane, is the hydrocarbon with the formula (C6H5)3CH.

•       This colorless solid is soluble in nonpolar organic solvents and not in water.

•       Triphenylmethane is the basic skeleton of many synthetic dyes called triarylmethane dyes, many of them are pH indicators, and some display fluorescence.

•       A trityl group in organic chemistry is a triphenylmethyl group Ph3C, e.g. triphenylmethyl chloride (trityl chloride) and the triphenylmethyl radical (trityl radical).

•       Triphenylmethane dye, any member of a group of extremely brilliant and intensely coloured synthetic organic dyes having molecular structures based upon that of the hydrocarbon triphenylmethane.

•       They have poor resistance to light and to chemical bleaches and are used chiefly in copying papers, in hectograph and printing inks, and in textile applications for which lightfastness is not an important requirement.

•       The triphenylmethane derivatives are among the oldest man-made dyes, a practical process for the manufacture of fuchsine having been developed in 1859.

•       Several other members of the class were discovered before their chemical constitutions were fully understood.

•        Crystal violet, the most important of the group, was introduced in 1883.

•       The range of colours is not complete but includes reds, violets, blues, and greens. They are applied by various techniques, but most belong to the basic class, which are adsorbed from solution by silk or wool, but have little affinity for cotton unless it has been treated with a mordant such as tannin.

Summary

•       C₁₄H₁₀is isomeric with anthracene

•       Structurally related to certain alkaloids like morphine and steroids like cholesterol

•       Synthesized by Pschorr and Haworth methods

•       Very reactive in 9,10 positions

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