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Pure Appl. Chem. 76(7-8), 1399-1408, 2004

Pure and Applied Chemistry

Vol. 76, Issues 7-8

Dendritic polyphenylazomethines: Synthesis, structure, and metal-assembling function

K. Yamamoto and M. Higuchi

Department of Chemistry, Faculty of Science & Technology, Keio University,
Yokohama 223-8522, Japan

Abstract: Dendritic polyphenylazomethines (DPAs) were synthesized as novel topological polymer ligands with pi-conjugated structures by the convergent method via dehydration of aromatic ketones with aromatic amines in the presence of TiCl4. DPA G4 molecules are re-
vealed to have a sphere-like structure with a 2.3-nm diameter and are regularly assembled without deformation of the molecule on a plate as observed by means of gel permeation chromatography (GPC), molecular modeling, transmission electron microscopy (TEM),
atomic force microscopy (AFM), and pi-A measurements. The stepwise radial complexation in DPAs with SnCl2 was observed as a stepwise shift in the isosbestic point in the UV-vis spectra. The number of added equivalents of SnCl2 required to induce a shift was in agreement with the number of imine groups present in the different shells of the DPAs. These spectral changes suggest that the complexation is proceeding in a stepwise fashion from the core
imines to the terminal imines of the DPAs, which was further supported by shell-selective reduction (SSR) of the imines.

*Lecture presented at the symposium "Recent advances in high performance polymers:A symposium in honour of Allan Hay", as part of the 39th IUPAC Congress and 86th Conference of the Canadian Society for Chemistry: Chemistry at the Interfaces, Ottawa, Canada, 10-15 August 2003. Other Congress presentations are published in this issue, pp. 1295-1603.


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