Conclusions
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1.
The condensation of α-fluoro-β-dimethylaminoacrolein aminal with ketones, β-dicarbonyl compounds, and CH-acids was investigated.
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2.
The synthesized dimethylamino-γ-fluorodienones (merocyanins) exist in the open form and are not cyclized to 2H-pyrans.
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3.
γ-Fluoro and γ,γ′-difluoroketocyanins were synthesized; their alkylation afforded alkoxynonamethine salts. Fluorine-containing thiapentacarbocyanin dyes were obtained from the latter compounds.
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4.
Dimethylammonium salts of tetracyano-γ-fluoropentadiene andγ-fluorotrimethinoxanine were synthesized. These compounds were used as the anionic components in obtaining cation-anion cyanin dyes.
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5.
The effect of the fluorine atom on the color of the synthesized dyes was investigated. It was shown that a fluorine atom in the polymethine chain behaves like an electron donor substituent. However, in sterically hindered merocyanins it elicits a hypsochromic shift of the absorption band even at even positions of the polymethine chain.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 3, pp. 636–645, March, 1989.
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Krasnaya, Z.A., Stytsenko, T.S., Bogdanov, V.S. et al. Synthesis of dyes containing fluorine atoms in the polymethine chain. Russ Chem Bull 38, 562–571 (1989). https://doi.org/10.1007/BF00958049
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DOI: https://doi.org/10.1007/BF00958049