Abstract
New cross-conjugated ω,ω′-dimethylaminopolyenes containing the central pyrane or N-methyldihydropyridine fragment were synthesized. In new compounds, the interaction of the aminopolyene chromophores occurs through the dicyanomethylidene, 1-cyano-1-(4-nitrophenyl)methylidene, or 1,3-dioxoindan-2-ylidene groups in position 4 of the heterocycle. The conformation of the synthesized compounds was determined by 2D 1H NMR spectroscopy (NOESY and ROESY): the chromophores are arranged at an acute or obtuse angle in the structures with the pyrane or dihydropyridine fragment, respectively. The conformational differences in polyenes result in a drastic change in their spectral properties: for the dyes with an acute angles between the chromophores, the long-wavelength absorption band is less intense, as a rule, than the shorter-wavelength band, while the situation is opposite for the compounds with an obtuse angle. The absorption spectra of the synthesized compounds with dinitrile and other acceptor groups lie in a longer-wavelength region than the absorption spectra of the corresponding compounds with carbonyl acceptor groups. The central bridging substituent NMe decreases the energy of interaction of the chromophores.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 2012–2022, September, 2013.
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Krasnaya, Z.A., Dorofeeva, E.O., Kachala, V.V. et al. Synthesis, spectral properties, and conformations of nonlinear cross-conjugated polyenes containing pyrane or dihydropyridine fragment. Russ Chem Bull 62, 2012–2022 (2013). https://doi.org/10.1007/s11172-013-0292-x
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DOI: https://doi.org/10.1007/s11172-013-0292-x