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- Title
The Remarkable Hyperchromicity of Ketohydrazone Dyes and Pigment Lakes Derived from 4-Morpholino-2-naphthol.
- Authors
Aiken, Stuart; Gabbutt, Christopher D.; Gillie, Lisa J.; Heywood, Jonathan D.; Jacquemin, Denis; Rice, Craig R.; Heron, B. Mark
- Abstract
The syntheses of a series of new ketohydrazone dyes and pigment lakes with a unique structural motif derived from 4-morpholino-2-naphthol are described. The morpholine substituent is responsible for the hypsochromically shifted absorption maxima with significantly enhanced molar extinction coefficients of the new dyes; this conclusion is supported by time-dependent DFT (TD-DFT) simulations. The location of the morpholine substituent at a sterically demanding site in the pigment lake obstructs further coordination of the bridging sulfonate groups in the solid state and prevents the formation of a 1-dimensional polymeric system, which is common for other pigment lakes.
- Subjects
DYES &; dyeing; MORPHOLINE; SULFONATES; ORGANOSULFUR compounds; NAPHTHOL
- Publication
European Journal of Organic Chemistry, 2013, Vol 2013, Issue 36, p8097
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201301218