Abstract
The asymmetric oxidative coupling polymerization of 6,6′-dihydroxy-2,2′-binaphthalene derivatives or methyl 3,7-dihydroxy-2-naphthoate, having an unsymmetric 2-naphthol structure, with copper catalysts under an O2 atmosphere was carried out. The polymerization using the CuCl-(S)-2,2′-isopropylidenebis(4-phenyl-2-oxazoline) catalyst afforded a polymer with a high cross-coupling selectivity of up to 99%, which showed a number average molecular weight of 5.0–9.1×103. To estimate the stereoselectivity during the polymerization, a model reaction was examined which resulted in good to high cross-coupling selectivities, while the enantioselectivities were low. The polymer composed of a homo-coupling unit showed a photoluminescence spectral pattern similar to that of the model compound. In contrast, a very different emission, which may be due to the excimer, from that of the model was observed for the polymer consisted of the cross-coupling unit.
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Temma, T., Takahashi, Y., Yoshii, Y. et al. Catalytic Oxidative Cross-Coupling Polymerization of Unsymmetric Binaphthol Derivatives Using Cu(I)-Bisoxazoline Complexes. Polym J 39, 524–530 (2007). https://doi.org/10.1295/polymj.PJ2006183
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DOI: https://doi.org/10.1295/polymj.PJ2006183