By Frances M. Hamer
Chapter I almost always 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 definite periods of Dyes regarding 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 homes and makes use of of Cyanine Dyes (pages 706–741):
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Extra info for Chemistry of Heterocyclic Compounds: The Cyanine Dyes and Related Compounds, Volume 18
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 ’ .
By condensing #-dimethylaminobenzaldehyde with a lepidinium or quinaldinium salt, in alcohol in the presence of piperidine, dyes of further types, XVIII and XIX, were made. It was considered that the formulae for the indole dyes, XVI and XVII, were so like those for cyanine, V, and isocyanine, VI, that there should be a greater similarity in properties than in fact exists. For, whereas, the indole dyes were unaffected by strong acids or 10 Chapter I by nitrous acid, the cyanines were discoloured by acid and with nitrous acid gave, momentarily, yellowish solids, which were regarded as nitrosoamines.
In 1922 the numbering of the benzothiazole ring differed from that accepted, by international agreement, in 1939. Thus XXXV would now be called 3,3'-diethylthiacyanine iodide, and XXXVI would be called 3,3'-diethylthiacarbocyanine iodide. The constitution of the thiacyanine, XXXV, was established" by its synthesis from u-aminothiophenol, by heating two molecular proportions with one of ethyl malonate, according to equation 4: (XXXVII) Chapter I 16 The resultant dibenzothiazolylmethane, XXXVII, formed a monoethiodide, XXXVIII.