A series of 2,6-dialkoxyanthracenes are synthesized and their photophysical properties in liquid solution and solid state are studied. Both spectral lineshapes and luminescence decay kinetics of these molecules in dilute solution or in a polymer matrix are identical.  We identify a conformational change in solution that leads to two emissive states that can interconvert.  In the solid state, the crystal structures of 2,6-dialkoxyanthracenes change significantly with lengthening alkoxy chains from methoxy to hexyloxy, evolving from herringbone structures to face-to-face two-dimensional sheets. The results from temperature-dependent experiments on single crystals indicate the intermolecular coupling between these molecules are akin to H-aggregates, which is different from the J-type aggregates seen in crystalline anthracene. By tuning the side chain length and modifying the crystal structures of 2,6-dialkoxyanthracenes, we can change the luminescence properties of the Frenkel excitons that exist in the crystal.

Crystal engineering of Frenkel excitons in 2,6-dialkoxyanthracenes

243rd National Meeting (2012)

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