Synthesis and characterization of bis-(3,5-dimethyl-4-hydroxyphenyl)(aryl)methanes as precursor for three state indicator

Add time:08/15/2019    Source:sciencedirect.com

A series of bis-(3,5-dimethyl-4-hydroxyphenyl)(aryl)methanes (1a–i) (where aryl=phenyl, 4-methyl-phenyl, 4-methoxy-phenyl, 4-hydroxyphenyl, 3,4-dimethoxyphenyl, 3,4,5-trimethoxyphenyl, 2-naphthyl, 4-nitrophenyl, 4-hydroxy-3-methoxyphenyl) are synthesized and characterized. Bis-(3,5-dimethyl-4-hydroxyphenyl)(phenyl)methane is a leuco-dye which can be easily oxidized to a quinone, 4-[(3′,5′-dimethyl-4′-hydroxyphenyl)(phenyl)methylene]-2,6-dimethylcyclohexa-2,5-dien-1-one, that exhibits three distinct coloured states in neutral, acidic and basic media/conditions. The single crystal X-ray structure of the quinone shows that it has a non-centrosymetric topology. Whereas the leuco-dye bis-(3,5-dimethyl-4-hydroxyphenyl) (phenyl)methane adopts a “propeller” conformation having one-dimensional H-bonding interactions along b-crystallographic axis.

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