The Remarkable Hyperchromicity of Ketohydrazone Dyes and Pigment Lakes Derived from 4-Morpholino-2-naphthol

Aiken, Stuart, Gabbutt, Christopher D., Gillie, Lisa .J., Heywood, Jonathan, Jacquemin, Denis, Rice, Craig R. and Heron, B. Mark (2013) The Remarkable Hyperchromicity of Ketohydrazone Dyes and Pigment Lakes Derived from 4-Morpholino-2-naphthol. European Journal of Organic Chemistry, 2013 (36). pp. 8097-8107. ISSN 1434-193X

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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.

Item Type:	Article
Subjects:	Q Science > QD Chemistry
Schools:	School of Applied Sciences
Related URLs:	Author Author Author Author
Depositing User:	Mark Heron
Date Deposited:	07 Nov 2013 16:42
Last Modified:	05 Mar 2014 13:40
URI:	http://eprints.hud.ac.uk/id/eprint/19090

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