Polyfluorinated triphenyl-4,5-dihydro-1H-pyrazoles with dendroid arylsulfanyl moieties as donor blocks in donor-acceptor chromophores

•An approach was developed for donor-acceptor dyes with dendroid moiety in the donor part.•Fluorine substitution in formylated decafluorotriarylpyrazoline was investigated.•Two synthetic sequences were compared in terms of efficiency and rationality.•An existing procedure for the introduction of the...

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Bibliographic Details
Published in:	Journal of fluorine chemistry Vol. 248; p. 109841
Main Authors:	Ishchenko, Roman A., Kargapolova, Irina Yu, Orlova, Natalia А., Shelkovnikov, Vladimir V., Maksimov, Alexander М., Ryazanov, Nikita D., Berezhnaya, Viktoria N., Chernonosov, Alexander А.
Format:	Journal Article
Language:	English
Published:	Lausanne Elsevier B.V 01-08-2021 Elsevier BV
Subjects:	Chromophores Dendroid moieties DFT calculations Donor-acceptor chromophores Fluorine Polyfluorinated pyrazolines Pyrazoles UV/Vis-spectra UV/Vis-spectra Polyfluorinated pyrazolines Dendroid moieties DFT calculations Donor-acceptor chromophores
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Summary:	•An approach was developed for donor-acceptor dyes with dendroid moiety in the donor part.•Fluorine substitution in formylated decafluorotriarylpyrazoline was investigated.•Two synthetic sequences were compared in terms of efficiency and rationality.•An existing procedure for the introduction of the dendroid moiety was thoroughly optimized. A series of novel donor-acceptor chromophores were synthesized using formylated derivatives of polyfluorinated triarylpyrazolines with branched moieties as donor blocks and dicyanoisophorone as acceptor. The nucleophilic substitution of fluorine with 4-hydroxypiperidine in decafluoropyrazoline was used to further functionalize the chromophore molecule. An existing method for introducing the dendroid moiety was improved. The properties of the final chromophores were estimated by DFT calculations. [Display omitted]
ISSN:	0022-1139 1873-3328
DOI:	10.1016/j.jfluchem.2021.109841