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Issue 42, 2009
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Water-solubilization of alkyloxo(methoxo)porphyrinatoantimony bromides

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In order to develop water-soluble porphyrins, alkyloxo(methoxo)porphyrinatoantimony bromides (alkyl = hexyl (1a), decyl (1b), dodecyl (1c), tetradecyl (1d), octadecyl (1e)) were prepared. 1 had more than 1 mmol dm−3 of solubility in water. From the dependence of the half-width of the bands in the absorption spectra and surface tension on the concentration of 1, it was estimated that 1b–d were present as aggregates in concentrations higher than 10 μmol dm−3. From the NMR analysis in D2O, it was deduced that the alkyloxo ligands of 1 were arranged alternately in the aggregates. The diameter of the aggregates of 1 in water was determined to be around 100 nm by the dynamic light scattering method. Since the solubilities of di(methoxo)tetraphenylporphyrinatoantimony bromide and 5-(4′-decyloxyphenyl)-10,15,20-triphenylporphyrinato(dimethoxo)antimony(V) bromide were low, it was calculated that the long alkyl axial ligands were requisite for the high solubility in water.

Graphical abstract: Water-solubilization of alkyloxo(methoxo)porphyrinatoantimony bromides

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Article information

08 Jun 2009
18 Aug 2009
First published
27 Aug 2009

Phys. Chem. Chem. Phys., 2009,11, 9766-9771
Article type

Water-solubilization of alkyloxo(methoxo)porphyrinatoantimony bromides

J. Matsumoto, S. Tanimura, T. Shiragami and M. Yasuda, Phys. Chem. Chem. Phys., 2009, 11, 9766
DOI: 10.1039/B911227H

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