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
• C14H10
is 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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