Enviar artigo por via de e-mail Synthesis, structure, electrochemistry, and photophysics of 2,5-dibenzylidenecyclopentanones containing in benzene rings substituents different in polarity
- Autores: Vatsadze S.Z.1, Gavrilova G.V.1, Zyuz’kevich F.S.2, Nuriev V.N.1, Krut’ko D.P.1, Moiseeva A.A.1, Shumyantsev A.V.1, Vedernikov A.I.2, Churakov A.V.3, Kuz’mina L.G.3, Howard J.A.4, Gromov S.P.1,2
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Afiliações:
- Department of Chemistry, M. V. Lomonosov Moscow State University
- Center of Photochemistry, Russian Academy of Sciences
- N. S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences
- Chemistry Department, Durham University
- Edição: Volume 65, Nº 7 (2016)
- Páginas: 1761-1772
- Seção: Full Articles
- URL: https://journal-vniispk.ru/1066-5285/article/view/238549
- DOI: https://doi.org/10.1007/s11172-016-1508-7
- ID: 238549
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Resumo
A series of cross-conjugated dienones was synthesized to study the dependence of physicochemical characteristics on the nature of substituents in the aromatic groups of symmetric cyclopentanone dibenzylidene derivatives. The structure of compounds was established by electronic, IR, and NMR spectroscopy and X-ray diffraction study. All the compounds obtained possess the E,E-geometry. In the crystalline state, the arrangement of the dienone molecules is unfavorable for the intermolecular [2+2] photocycloaddition to take place. The low-temperature phases transition for unsubstituted diphenyl derivative of cyclopentanone was detected using variable-temperature X-ray diffraction and differential scanning calorimetry. Oxidation and reduction potentials of the dienones were measured by cyclic voltammetry. Their dependence on the nature and placement of substituents in the benzene rings was demonstrated. A linear correlation (R = 0.9343) between the difference of electrochemical oxidation and reduction potentials and the energy of the long-wavelength absorption maximum was found, that allows us to recommend the use of the data obtained in the correlation analysis of other compounds of this class.
Sobre autores
S. Vatsadze
Department of Chemistry, M. V. Lomonosov Moscow State University
Autor responsável pela correspondência
Email: szv@org.chem.msu.ru
Rússia, Build. 3, 1 Leninskie Gory, Moscow, 119991
G. Gavrilova
Department of Chemistry, M. V. Lomonosov Moscow State University
Email: szv@org.chem.msu.ru
Rússia, Build. 3, 1 Leninskie Gory, Moscow, 119991
F. Zyuz’kevich
Center of Photochemistry, Russian Academy of Sciences
Email: szv@org.chem.msu.ru
Rússia, 7A-1 ul. Novatorov, Moscow, 119421
V. Nuriev
Department of Chemistry, M. V. Lomonosov Moscow State University
Email: szv@org.chem.msu.ru
Rússia, Build. 3, 1 Leninskie Gory, Moscow, 119991
D. Krut’ko
Department of Chemistry, M. V. Lomonosov Moscow State University
Email: szv@org.chem.msu.ru
Rússia, Build. 3, 1 Leninskie Gory, Moscow, 119991
A. Moiseeva
Department of Chemistry, M. V. Lomonosov Moscow State University
Email: szv@org.chem.msu.ru
Rússia, Build. 3, 1 Leninskie Gory, Moscow, 119991
A. Shumyantsev
Department of Chemistry, M. V. Lomonosov Moscow State University
Email: szv@org.chem.msu.ru
Rússia, Build. 3, 1 Leninskie Gory, Moscow, 119991
A. Vedernikov
Center of Photochemistry, Russian Academy of Sciences
Email: szv@org.chem.msu.ru
Rússia, 7A-1 ul. Novatorov, Moscow, 119421
A. Churakov
N. S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences
Email: szv@org.chem.msu.ru
Rússia, 31 Leninsky prosp., Moscow, 119991
L. Kuz’mina
N. S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences
Email: szv@org.chem.msu.ru
Rússia, 31 Leninsky prosp., Moscow, 119991
J. Howard
Chemistry Department, Durham University
Email: szv@org.chem.msu.ru
Reino Unido da Grã-Bretanha e Irlanda do Norte, South Road, Durham, DH1 3LE
S. Gromov
Department of Chemistry, M. V. Lomonosov Moscow State University; Center of Photochemistry, Russian Academy of Sciences
Email: szv@org.chem.msu.ru
Rússia, Build. 3, 1 Leninskie Gory, Moscow, 119991; 7A-1 ul. Novatorov, Moscow, 119421
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