Zinc and metal-free amphiphilic phthalocyanines (pcs) substituted by four or eight tri(ethylene oxide) chains (3,6,9-trioxadecyloxy groups) {(H2(4EGpc), [Zn(4EGpc)], H2(8EGpc), and [Zn(8EGpc)] in Fig. 1)} have been prepared in order to study their aggregation in water, dioxane, and dioxane/water mixtures, their complexation phenomena with guest molecules in benzene, and mesomorphism in the neat state. In particular, tetra-substituted pcs have C4h symmetry and do not contain other positional isomers. [Zn(8EGpc)] forms aggregates in water and water–organic solvent mixtures; the extent of this was examined by electronic absorption and fluorescence spectroscopy. 1H NMR and fluorescence spectroscopy indicated that H2- and [Zn(8EGpc)] form inclusion complexes with quinones in benzene via hydrogen bonding. Benzoquinones with more hydroxy groups form complexes more effectively, plausibly laterally outside of the pc plane. From the higher field shift of the 1H singals of 2,2′-dihydroxy-1,1′-binaphthyl (BINAP) in the presence of [Zn(8EGpc)], BINAP molecules were suggested to lie above or below the pc plane. The mesomorphism of H2(8EGpc), [Zn(4EGpc)], and H2(4EGpc) was studied. In the case of H2(8EGpc), the discotic hexagonal ordered columnar (Dho) phase was seen in the range of from room temperature to 265 °C. However, liquid-crystalline phases were not observed for H2(4EGpc) and [Zn(4EGpc)].
In order to obtain discotic compounds exhibiting a cubic mesophase, we synthesised two new series of discotic compounds, 2,3,9,10,16,17,23,24-octakis(4-alkoxyphenoxy)phthalocyaninato
An electrochromic-type electronic paper was prepared using nanocomposites that consisted of silica nanoparticles (silica 60 wt %) and polyamide pulp. Its light scattering, ion transport, and aqueous electrolyte retention characteristics were examined. As a result, the shape of the nanocomposites was completely self-standing, though it could be impregnated with about nine times as much water on a weight basis. Moreover, its light scattering property was extremely similar to paper. Because of the impregnation of a large amount of water, the ion transport property of the nanocomposites was the same as that of the electrolyte solution without the nanocomposites. The nanocomposites was impregnated using an aqueous solution in which bismuthyl perchlorate (redox species), copper perchlorate, perchloric acid, sodium perchlorate, hydroquinone (electron mediator) and 2-buthyne-1,4-diol (leveling agent) were dissolved. The electronic paper was then prepared by sandwiching the nanocomposites between an indium-tin-oxide transparent electrode and a copper sheet. This electronic paper utilizes the reversible codeposition reaction of black Bi-Cu from bismuthyl perchlorate and copper(II) ions. The characteristics of this electronic paper were examined, and excellent characteristics with a white reflectivity of 65%, black reflectivity of 6.4%, contrast ratio of 10:1, operating life of over 1 × 10 6 cycles and open-circuit memory of at least 1 month were obtained. In addition, its driving voltage was 1.2 V, and the write time was 500 ms.
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