Phototransformations of acrylamide derivatives of piperazine-substituted polyfluorinated chalcones

Phototransformations of acrylamide derivatives of piperazine-substituted polyfluorinated chalcones Full article

Journal

Journal of Photochemistry and Photobiology A: Chemistry
ISSN: 1010-6030

Output data

Year: 2021, Volume: 406, Article number : 112973, Pages count : DOI: 10.1016/j.jphotochem.2020.112973

Tags

Dimerization; free-radical polymerization; Intramolecular cyclization; MALDI-TOF spectroscopy; Photoresist; polyfluorinated chalcones

Authors

Derevyashkin S.V. ^1,2 , Soboleva E.A. ¹ , Shelkovnikov V.V. ^1,3 , Orlova N.A. ¹ , Malakhov I.A. ³ , Berezhnaya V.N. ¹ , Savina E.D. ⁴ , Tsentalovich Y.P. ⁴

Affiliations

1	(Scopus) Laboratory of Organic Photosensitive Materials, Novosibirsk Institute of Organic Chemistry SB RAS, Lavrentieva 9, Novosibirsk, 630090, Russian Federation
2	(Scopus) Institute of Laser Physics SB RAS, Lavrentieva 15-b, Novosibirsk, 630090, Russian Federation
3	(Scopus) Department of Optical Information Technologies, Novosibirsk State Technical University, Marx 20, Novosibirsk, 630073, Russian Federation
4	(Scopus) Laboratory of Proteomics and Metabolomics, International Tomographic Center SB RAS, Institutskaya 3a, Novosibirsk, 630090, Russian Federation

Phototransformations of acrylamide derivatives of the piperazino-substituted polyfluorochalcones (APPFC) were studied by UV, IR, Raman, and NMR spectroscopy. It has been shown that two types of photochemical reactions occur in the films of APPFC: free-radical polymerization of acrylic fragments and cyclodimerization of the carbon-carbon double bond in a chalcone. It was shown that in polyfluorochalcones PFCh-1, PFCh-2, trans-cis isomerization of chalcone occurs with the subsequent formation of dimers. Along with this, a competitive reaction of intramolecular photocyclization occurs in PFCh-2 via the dehydrofluorination. Based on MALDI-TOF mass spectra, the structural formulas of the possible dimeric and oligomeric fragments of polyfluorochalcones formed in the films were proposed. The obtained spectral data indicate that, according to the efficiency of the formation of photocrosslinked films, studied polyfluorochalcones can be arranged in the following order: TAFCh >> PFCh-1 > > PFCh-2. © 2020 Elsevier B.V.

Derevyashkin S.V. , Soboleva E.A. , Shelkovnikov V.V. , Orlova N.A. , Malakhov I.A. , Berezhnaya V.N. , Savina E.D. , Tsentalovich Y.P.
Phototransformations of acrylamide derivatives of piperazine-substituted polyfluorinated chalcones
Journal of Photochemistry and Photobiology A: Chemistry. 2021. V.406. 112973 . DOI: 10.1016/j.jphotochem.2020.112973 WOS Scopus OpenAlex

Published print:

Feb 1, 2021

Web of science:	WOS:000600925300009
Scopus:	2-s2.0-85094210761
OpenAlex:	W3097606746

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Scopus	2
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