By Frances M. Hamer
Chapter I ordinarily Introductory (pages 1–31):
Chapter II Methincyanines (pages 32–76):
Chapter III Methincyanines with Substituents at the Chain (pages 77–85):
Chapter IV Symmetrical Trimethincyanines (pages 86–115):
Chapter V Unsymmetrical Trimethincyanines (pages 116–147):
Chapter VI Trimethincyanines with Substituents at the Chain (pages 148–199):
Chapter VII Symmetrical and Unsymmetrical Pentamethincyanines, together with people with Substituents at the Chain (pages 200–243):
Chapter VIII Symmetrical and Unsymmetrical Heptamethincyanines, together with people with Substituents at the Chain; Polymethincyanines (pages 244–269):
Chapter IX Cyanines during which the Odd?Numbered Carbon Chain, Which hyperlinks the Nuclei, or a part of it, is Cyclic (pages 270–291):
Chapter X diversifications within the Nuclei Which input into Cyanine Molecules (pages 292–350):
Chapter XI Bases, together with a few With Substituents at the Chain, of Which Cyanines are the Quaternary Salts (pages 351–374):
Chapter XII Azacyanines, together with Dyes Substituted at the Chain, and Bases of Which the Quaternary Salts are Azacyanines (pages 375–397):
Chapter XIII sure periods of Dyes concerning Cyanines (pages 398–510):
Chapter XIV Merocyanines (pages 511–611):
Chapter XV Trinuclear and Polynuclear Cyanines (pages 612–684):
Chapter XVI the connection among color and structure within the Cyanine sequence (pages 685–705):
Chapter XVII Photographic Sensitisation and a few different houses and makes use of of Cyanine Dyes (pages 706–741):
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Extra resources for Chemistry of Heterocyclic Compounds: The Cyanine Dyes and Related Compounds, Volume 18
C. 47 Although two formulae had been suggested previously, one did not agree with the analytical results and neither explained the colour of the dye. Careful analysis showed that two molecules of quinaldine ethiodide were concerned in the formation of pinacyanol, and that the formaldehyde residue did enter into the molecule. The probable reaction for dye formation was therefore: It was proved that a quinoline &iodide, if present, takes no direct part in the condensation. Pinacyanol bromide was oxidised by heating with dilute nitric acid and from the reaction mixture quinaldinic acid ethonitrate, XXXI, was isolated in about 90% yield.
In 1883 it was found that synthetic quinoline did not give rise to cyanine and it was demonstrated that it is the mixture of quinoline alkiodide and lepidme . C#J - + CioHeN*%HJ Cs&&gI + Ha -t HI (1) Two sets of observers independentlyaK@ obtained a redder dye by the action of alkali on a mixture of quinoline ethiodide and quinaldine ethiodide. For this dye, one pair of workers proposed the name diethylisocyanine iodide and they considered that it also had the formula caaH28NP In 1886 it was noted that when 2,4-dimethylquinoline methiodide was treated with sodium hydroxide solution and left standing in the air, there was formed a violet-blue dye, which was considered to be related to cyanine,* and was later called Dicyanine.
At the beginning of this century, various photographic sensitisers were on the market, but nowadays the nature of the particular sensitisers used is a trade secret and practically none are for sale. 2. The Chemistry of the First Sixty-Three Years (up to 1919) It was in 1856 that C. H. Greville Williams, who was then working at Glasgow University and was twenty-seven years old, noted the tendency of quinoliniurn salts to give intense colours,l6 for instance on heating with silver oxide. I6 Greville Williams, in comparing quinolines obtained by distillation of coal, bituminous shale, bone oil, and cinchonine, found general agreement in physical properties, with minor differences, and the most striking of these w a ~ ~ that ’ .
Chemistry of Heterocyclic Compounds: The Cyanine Dyes and Related Compounds, Volume 18 by Frances M. Hamer