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The Remarkable Hyperchromicity of Ketohydrazone Dyes and Pigment Lakes Derived from 4‐Morpholino‐2‐naphthol (Eur. J. Org. Chem. 36/2013)
Author(s) -
Aiken Stuart,
Gabbutt Christopher D.,
Gillie Lisa J.,
Heywood Jonathan D.,
Jacquemin Denis,
Rice Craig R.,
Heron B. Mark
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201390103
Subject(s) - chemistry , pigment , morpholino , substituent , crystal structure , hypsochromic shift , hydrate , stereochemistry , organic chemistry , fluorescence , biochemistry , zebrafish , gene , physics , quantum mechanics
The cover picture shows the crystal structure of a new, orange, Ca‐containing pigment lake derived from diazo coupling of orthanilic acid to 4‐morpholino‐2‐naphthol. The crystal structure is of a novel type in which the morpholino substituent has prevented the formation of a 1‐dimensional polymeric system, which is common to previously reported naphthol‐derived pigment lakes. The pigment has been obtained in three physical forms; as a hydrate, a DMSO solvate and as a desolvated form. Azo dyes derived from 4‐morpholino‐2‐naphthol exhibit a small hypsochromic shift but with enhanced molar absorbtivity compared with dyes derived from 2‐naphthol. This pigment lake may have application for the coloration of inks, paints and plastics. Details are discussed in the article by B. M. Heron et al. on p. 8097 ff.