2,6-Bis(triethoxysilyl)anthracene was first synthesized by rhodium-catalyzed disilylation of 2,6-bis(trifluoromethanesulfonyloxy)
anthracene with triethoxysilane. Using the new precursor, anthracene-bridged
periodic mesostructured organosilicas were obtained without cleavage of the Si–C bondings. The anthracene-
silica hybrids showed absorption at near ultraviolet region and blue–green fluorescence with a
quantum yield of 0.13–0.15. The absorption and fluorescence behaviors of the 2,6-anthracene-silica
hybrid film were compared with those of the previously reported 9,10-anthracene-silica hybrid film.
Their absorbances suggest that the 2,6-anthracene groups were packed more densely than the
9,10-anthracene groups in the mesoporous frameworks due to smaller steric hindrance. In spite of the
densely packed structure, the 2,6-anthracene-silica hybrid film showed fluorescence emission at shorter
wavelengths and a higher quantum yield than those of the 9,10-anthracene-silica hybrid film, suggesting
relatively weak interaction between the anthracene groups in the framework because of restriction of
intramolecular rotation motion for substitution at 2,6-positions of anthracene. Dilution of the anthracene
groups in the framework with trimethoxysilane promoted monomeric fluorescence and an increase of its
quantum yield up to 0.18.
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