The bridged peri-aroylnaphthalene compound having cyclohexane-cis-1,2-dioxy-hinge moiety connecting two benzoyl groups was
successfully synthesized through the nucleophilic aromatic substitution of 1,8-bis(4-fluorobenzoyl)-2,7-dimethoxynaphthalene and
cyclohexane-cis-1,2-diol. The compound consists of two ingredients in solution. The ingredients were successfully separated by repeated
preparative thin layer chromatographical treatments to give stable solids. By the aid of 1H NMR spectroscopic time course tracing, the
ingredients have proved to undergo mutual transformations between them to yield an equilibrium mixture of constant fraction values by
standing the individual solution within several weeks, revealing that the ingredients are conformational isomers to each other. Spatial
organizations of the isomers of the bridged compound in solution have been elucidated by difference NOE measurement showing rough
geometry of the isomers as two “extended” forms.
Key words: molecular structure in solution, bridged peri-aroylnaphthalene compound, cyclohexane-cis-1,2-dioxy-hinge, stable
conformational isomer.
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