Abstract
A series of halogenated compounds, (E,E,E)-1,6-di(4-X-phenyl)hexa-1,3,5-trienes (1: X = F, 2: X = Cl, 3: X = Br, 4: X = I), were synthesized and their crystal structures and fluorescence emission properties were systematically investigated. Single-crystal X-ray analysis reveals that molecules are arranged via X/X halogen bonds and/or CH/X-type hydrogen bonds to form a herringbone structure in 1 and π-stacked structures in 2–4. In the structures of 2 and 3, which are almost isomorphous, the distance and displacement for the nearest stacking molecules are smaller than those in 4. Although the structures of 2–4 are basically not greatly different from each other, the nearest-neighbor arrangements are π-stacked in 2 and 3, but herringbone in 4. Steady-state and time-resolved measurements show that the solid-state fluorescence properties also strongly depend on the halogen size. The fluorescence spectra are red-shifted and the Stokes shifts are large in 2 and 3 relative to those in 1 and 4, resulting from the ...
Published Version
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