The Synthesis, X-ray Structure Analysis and Photophysical Characterization of 2-(9-Anthrylmethylideneamino)-5-methylphenol

Abstract

The Schiff base 2-(9-anthrylmethylideneamino)-5-methylphenol has been prepared in good yield (55%) from commercially available starting materials. The photophysical properties of this compound and its precursor have been determined. The room temperature absorption spectra of both in various solvents exhibited two π → π* transitions that had similar maxima, one that was more intense at approximately 260 nm and a weaker one at approximately 400 nm. Solutions of both compounds in methylcyclohexane and propanenitrile were luminescent at room temperature with maxima in the range 450–500 nm. The emission spectra of both at 77 K in methylcyclohexane solution were similar and exhibited vibrational structure with maxima in the range 460–522 nm. At room temperature and 77 K both compounds had short excited state lifetimes that characterized their emission as fluorescence. The title compound, C22H17NO, crystallized in the triclinic space group $$ P{\bar{\text{1}}} $$ with a = 8.5533 (5) A, b = 14.0926 (10) A, c = 14.9382 (11) A, α = 104.204 (6)°, β = 106.480 (5)°, γ = 105.091 (5)°, V = 1564.9 (2) A3, T = 90 K, D c = 1.322 Mg m−3, Z = 4, R = 0.033. The X-ray structure and photophysical properties of the title compound (1) were determined.