Synthesis and spectroscopic properties of propeller type 2,4,6-tri(anthracen-9-yl)-1,3,5-triazine?

RSC Advances Pub Date: 2015-06-04 DOI: 10.1039/C5RA08833J

Abstract

The novel propeller type compound, 2,4,6-tri(anthracen-9-yl)-1,3,5-triazine (TAT) with C3 symmetry was synthesized by using 9-anthryl lithium with 1,3,5-trichlorotriazine or 2-chloro-4,6-dimethoxy-1,3,5-triazine in the presence of palladium catalyst in 22–48% yield. Another two propeller-like compounds, 2-(anthracen-9-yl)-4,6-dimethoxy-1,3,5-triazine (3) and 2,4-di(anthracen-9-yl)-6-methoxy-1,3,5-triazine (4) were obtained at the same time. The propeller type structures of TAT, 3 and 4 were confirmed by crystal analysis and theoretical calculations. The intramolecular C–C bond rotations between the anthryl groups and the triazine units in molecules TAT, 3 and 4 were regarded as the key factor to understand their spectroscopic behaviors in fluid medium and rigid solution.

Graphical abstract: Synthesis and spectroscopic properties of propeller type 2,4,6-tri(anthracen-9-yl)-1,3,5-triazine
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