Synthesis, structure, electrochemistry, and photophysics of 2,5-dibenzylidenecyclopentanones containing in benzene rings substituents different in polarity


如何引用文章

全文:

开放存取 开放存取
受限制的访问 ##reader.subscriptionAccessGranted##
受限制的访问 订阅存取

详细

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.

作者简介

S. Vatsadze

Department of Chemistry, M. V. Lomonosov Moscow State University

编辑信件的主要联系方式.
Email: szv@org.chem.msu.ru
俄罗斯联邦, Build. 3, 1 Leninskie Gory, Moscow, 119991

G. Gavrilova

Department of Chemistry, M. V. Lomonosov Moscow State University

Email: szv@org.chem.msu.ru
俄罗斯联邦, Build. 3, 1 Leninskie Gory, Moscow, 119991

F. Zyuz’kevich

Center of Photochemistry, Russian Academy of Sciences

Email: szv@org.chem.msu.ru
俄罗斯联邦, 7A-1 ul. Novatorov, Moscow, 119421

V. Nuriev

Department of Chemistry, M. V. Lomonosov Moscow State University

Email: szv@org.chem.msu.ru
俄罗斯联邦, 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
俄罗斯联邦, Build. 3, 1 Leninskie Gory, Moscow, 119991

A. Moiseeva

Department of Chemistry, M. V. Lomonosov Moscow State University

Email: szv@org.chem.msu.ru
俄罗斯联邦, Build. 3, 1 Leninskie Gory, Moscow, 119991

A. Shumyantsev

Department of Chemistry, M. V. Lomonosov Moscow State University

Email: szv@org.chem.msu.ru
俄罗斯联邦, Build. 3, 1 Leninskie Gory, Moscow, 119991

A. Vedernikov

Center of Photochemistry, Russian Academy of Sciences

Email: szv@org.chem.msu.ru
俄罗斯联邦, 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
俄罗斯联邦, 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
俄罗斯联邦, 31 Leninsky prosp., Moscow, 119991

J. Howard

Chemistry Department, Durham University

Email: szv@org.chem.msu.ru
英国, 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
俄罗斯联邦, Build. 3, 1 Leninskie Gory, Moscow, 119991; 7A-1 ul. Novatorov, Moscow, 119421

补充文件

附件文件
动作
1. JATS XML

版权所有 © Springer Science+Business Media New York, 2016