Synthesis and spectroscopic properties of cross-conjugated ketones and meso-substituted tridecamethine salts containing the pyran or pyridone fragment |
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Authors: | Krasnaya Zh A Smirnova Yu V Shvedova L A Tatikolov A S Kuz"min V A |
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Institution: | (1) N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation;(2) N. M. Emanuel" Institute of Biochemical Physics, Russian Academy of Sciences, 4 ul. Kosygina, 119991 Moscow, Russian Federation |
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Abstract: | The reactions of substituted 4H-pyrones and N-methyl-2,6-dimethylpyridone with dimethylformamide acetal and aminal acetals of conjugated -dimethylaminoaldehydes were studied. Cross-conjugated ketones and meso-ethoxy(dialkylamino)tridecamethine salts containing the pyran or pyridone fragment were synthesized and their spectroscopic properties were investigated. The replacement of the bridging O atom by the NMe group precludes an interaction between chromophores in cross-conjugated ketone and the related tridecamethine salt. In addition, the insertion of a meso-amino substituent into the polymethine chain of the salts containing the central pyrylium fragment leads to a sharp weakening of the chromophore interaction. In spite of the dramatic differences in the UV spectra of ketocyanines containing the bridging O or NMe fragments, these dyes have similar 13C NMR spectra. |
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Keywords: | polyenic bis-aminoketone pyran and pyridone fragments aminal acetals tridecamethine salts protonation prototropic equilibrium chromophore interaction |
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