NMR analysis of Nile Blue (C. I. Basic Blue 12) and Thionine (C. I. 52000) in solution

Hazafy, David and Salvia, Marie-Virginie and Mills, Andrew and Hutchings, Michael G. and Evstigneev, Maxim P. and Parkinson, John A. (2011) NMR analysis of Nile Blue (C. I. Basic Blue 12) and Thionine (C. I. 52000) in solution. Dyes and Pigments, 88 (3). pp. 315-325. ISSN 0143-7208 (https://doi.org/10.1016/j.dyepig.2010.07.014)

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Abstract

The dyes Nile Blue (C. I. Basic Blue 12, NB) and Thionine (C. I. 52000, TH) were examined in both ionic and neutral forms in different solvents using NMR and UV-visible Spectroscopy to firmly establish the structures of the molecules and to assess the nature and extent of their aggregating characteristics. 1H and 13C NMR assignments and chemical shift data were used along with (for NB) nuclear Overhauser effect information enabling a structure for self-assembly to be proposed. In both cases these data were supplemented with variable temperature, dilution and diffusion-based experimental results using 1H NMR spectroscopy thereby enabling the extended aggregate structures to be assessed in terms of the relative strength of self-association and the extent to which extended aggregates could form. Full and detailed solution phase NMR analysis of such dyes, especially the two studied in this context, have either not been widely reported or have not been studied to the depth presented here. The data and their interpretation form an important addition to the analysis of this class of dye compounds and provide additional insight into the effects of self-assembly on the behaviour of such molecules in various solution-phase environments.

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