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Journal Articles

Piezoluminescence and liquid crystallinity of 4,4'-(9,10-Anthracenediyl)bispyridinium salts

Komoto, Shigeo*; Chuko, Tomotaka*; Hisamatsu, Shugo; Okuda, Yasuhiro*; Masu, Hyuma*; Takahashi, Masahiro*; Kishikawa, Keiki*

Crystal Growth & Design, 15(6), p.2723 - 2731, 2015/05

 Times Cited Count:9 Percentile:64.62(Chemistry, Multidisciplinary)

Piezoluminescence and liquid crystallinity of anthracene-based bispyridinium salts were investigated in stimulus responsive luminescent organic crystals and luminescent ionic liquid crystals. The salts possess an anthracene moiety as a fluorophore in their center, and the pyridiniums attached to the anthracene moiety are substituted with trialkoxybenzyl groups. Single crystals of the salts bearing two trimethoxybenzyl groups were obtained as solvates. Ethyl acetate, acetone, and dioxane solvates of the chlorides have almost the same crystal structures with one-dimensional channels. Grinding of the solvated crystals caused the extrusion of the included solvent molecules, which resulted in the red shifts of their fluorescence in the solid state. Tris(octyloxy)benzyl and tris(dodecyloxy)benzyl derivatives exhibited rectangular columnar liquid crystals upon being heated for their bromide and tetrafluoroborate salts and upon being cooled for their hexafluorophosphate salts.

Journal Articles

Pairwise packing of anthracene fluorophore; Hydrogen-bonding-assisted dimer emission in solid state

Hisamatsu, Shugo; Masu, Hyuma*; Takahashi, Masahiro*; Kishikawa, Keiki*; Komoto, Shigeo*

Crystal Growth & Design, 15(5), p.2291 - 2302, 2015/04

 Times Cited Count:53 Percentile:97.65(Chemistry, Multidisciplinary)

Anthracene derivatives possessing a carbamate group and an ester group at their 9- and 10-positions, respectively, were prepared to furnish pairwise packing of anthracene fluorophores in their crystal structures. They were nonluminescent in ethanol solution and showed AIE (aggregation-induced emission) in aqueous ethanol solution and in solid state. Crystal structure analysis of them showed that the H-bonding networks involved in their crystal structures could be classified into four patterns, H-bonding between the carbamate and the ester carbonyl (motifA), H-bonding between the carbamate and the ester oxygen atom (motif B), H-bonded cyclic dimer of carbamate moieties (motif C), and H-bonded chain among carbamate moieties (motif D). Compounds with pairwisely packed anthracene fluorophores showed dimer emission with the longer fluorescence wavelength than others without the pair formation.

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