Abstract
Dendritic polyphenylazomethines (DPAs) with a regularly branched structure and a single molecular weight were synthesized using the convergent method. DPA derivatives having tris(thienylphenyl)amine and tetraphenylporphyrin as the core (TPA-DPAs and Por-DPAs) and aniline-capped DPAs were obtained during the dehydration of the DPA dendrons with tris(4-aminothienylphenyl)amine, tetra(4-aminophenyl)porphyrin, and aniline, respectively. We exploited the more efficient synthetic method of DPAs, and successfully obtained the fifth generation of DPA (DPA G5). Stepwise radial complexation with SnCl2 in DPAs, TPA-DPAs, Por-DPAs, and aniline-capped DPAs, was found as stepwise shifts of the isosbestic point during the UV–vis spectroscopic observation. This complexation behavior was supported by the shell-selective reduction of the imines. Using the shell-selective reduction method and the terminal-modification method of the DPAs, the core and terminals of DPAs were functionalized by a ferrocene unit(s), respectively. FeCl3 molecules were also complexed with the imines of the DPAs in a stepwise fashion. Encapsulation/releasing of Fe ions in DPA was electrochemically controlled due to the different complexation ability of Fe(II) and Fe(III) ions with the imines. TPA-DPAs were applied as hole-transporting materials in EL devices. Their efficiency was found to be enhanced when complexing with SnCl2.
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Yamamoto, K., Higuchi, M. Fine-control of Metal Assembling in Dendritic Polyphenylazomethines. Polym J 36, 577–586 (2004). https://doi.org/10.1295/polymj.36.577
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DOI: https://doi.org/10.1295/polymj.36.577