Synthesis of new star-like triply ferrocenylated compounds

Juan C. Santos, Franco Madrid-Moliné, Carlos A. Cisternas, Frédéric Paul, Carlos A. Escobar, Paola Jara-Ulloa, Alexander Trujillo

Resultado de la investigación: Article

Resumen

New ferrocenyl-subtituted compounds containing two different central cores (isocyanurate and 1,3,5-phenylene) and extended by two kinds of branches bearing both vinyl ferrocenyl (1 and 3) and cross-conjugated ferrocenyl-chalcone (2, 4 and 5) as endgroups have been synthetized and characterized both spectroscopically and electrochemically. These molecules have been synthesized in order to investigate the electronic properties imparted by both types of branches when they are connected to the central core. For all compounds, electrochemical studies have showed a simultaneous oxidation of all ferrocene units present in each compound. For all of them, except for compound 2, a chemically reversible oxidation wave on the voltammograms has been observed. In contrast, for compound 2, a chemically irreversible oxidation wave is obtained. Moreover, the vinyl ferrocenyl derivatives have presented a lower redox peak potential with respect to ferrocene standard compound, and the ferrocenyl-chalcone bearing derivatives, in accordance with a change in the electron releasing capability of these endgroups, have been oxidized at a higher potential. Bathochromic shifts of the active transitions in Uv-Vis region have been observed, which are associated to the presence of carbonyl groups in those molecular structures containing it. These results are in agreement with theoretically calculated transition energies, which have been obtained for compounds 1 and 2 using Time Dependent Density Functional Theory (TD-DFT).

IdiomaEnglish
Páginas95-100
Número de páginas6
PublicaciónInorganica Chimica Acta
Volumen486
DOI
EstadoPublished - 24 feb 2019

Huella dactilar

Bearings (structural)
Stars
Chalcone
stars
Oxidation
oxidation
synthesis
Derivatives
releasing
Electronic properties
Molecular structure
Density functional theory
molecular structure
density functional theory
Molecules
Electrons
shift
electronics
molecules
electrons

Keywords

    ASJC Scopus subject areas

    • Physical and Theoretical Chemistry
    • Inorganic Chemistry
    • Materials Chemistry

    Citar esto

    Santos, Juan C. ; Madrid-Moliné, Franco ; Cisternas, Carlos A. ; Paul, Frédéric ; Escobar, Carlos A. ; Jara-Ulloa, Paola ; Trujillo, Alexander. / Synthesis of new star-like triply ferrocenylated compounds. En: Inorganica Chimica Acta. 2019 ; Vol. 486. pp. 95-100.
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    abstract = "New ferrocenyl-subtituted compounds containing two different central cores (isocyanurate and 1,3,5-phenylene) and extended by two kinds of branches bearing both vinyl ferrocenyl (1 and 3) and cross-conjugated ferrocenyl-chalcone (2, 4 and 5) as endgroups have been synthetized and characterized both spectroscopically and electrochemically. These molecules have been synthesized in order to investigate the electronic properties imparted by both types of branches when they are connected to the central core. For all compounds, electrochemical studies have showed a simultaneous oxidation of all ferrocene units present in each compound. For all of them, except for compound 2, a chemically reversible oxidation wave on the voltammograms has been observed. In contrast, for compound 2, a chemically irreversible oxidation wave is obtained. Moreover, the vinyl ferrocenyl derivatives have presented a lower redox peak potential with respect to ferrocene standard compound, and the ferrocenyl-chalcone bearing derivatives, in accordance with a change in the electron releasing capability of these endgroups, have been oxidized at a higher potential. Bathochromic shifts of the active transitions in Uv-Vis region have been observed, which are associated to the presence of carbonyl groups in those molecular structures containing it. These results are in agreement with theoretically calculated transition energies, which have been obtained for compounds 1 and 2 using Time Dependent Density Functional Theory (TD-DFT).",
    keywords = "Cyclic voltammetry, Redox-active ferrocenyl-based compounds, Time-dependent DFT, Uv-Vis absorption",
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    Synthesis of new star-like triply ferrocenylated compounds. / Santos, Juan C.; Madrid-Moliné, Franco; Cisternas, Carlos A.; Paul, Frédéric; Escobar, Carlos A.; Jara-Ulloa, Paola; Trujillo, Alexander.

    En: Inorganica Chimica Acta, Vol. 486, 24.02.2019, p. 95-100.

    Resultado de la investigación: Article

    TY - JOUR

    T1 - Synthesis of new star-like triply ferrocenylated compounds

    AU - Santos, Juan C.

    AU - Madrid-Moliné, Franco

    AU - Cisternas, Carlos A.

    AU - Paul, Frédéric

    AU - Escobar, Carlos A.

    AU - Jara-Ulloa, Paola

    AU - Trujillo, Alexander

    PY - 2019/2/24

    Y1 - 2019/2/24

    N2 - New ferrocenyl-subtituted compounds containing two different central cores (isocyanurate and 1,3,5-phenylene) and extended by two kinds of branches bearing both vinyl ferrocenyl (1 and 3) and cross-conjugated ferrocenyl-chalcone (2, 4 and 5) as endgroups have been synthetized and characterized both spectroscopically and electrochemically. These molecules have been synthesized in order to investigate the electronic properties imparted by both types of branches when they are connected to the central core. For all compounds, electrochemical studies have showed a simultaneous oxidation of all ferrocene units present in each compound. For all of them, except for compound 2, a chemically reversible oxidation wave on the voltammograms has been observed. In contrast, for compound 2, a chemically irreversible oxidation wave is obtained. Moreover, the vinyl ferrocenyl derivatives have presented a lower redox peak potential with respect to ferrocene standard compound, and the ferrocenyl-chalcone bearing derivatives, in accordance with a change in the electron releasing capability of these endgroups, have been oxidized at a higher potential. Bathochromic shifts of the active transitions in Uv-Vis region have been observed, which are associated to the presence of carbonyl groups in those molecular structures containing it. These results are in agreement with theoretically calculated transition energies, which have been obtained for compounds 1 and 2 using Time Dependent Density Functional Theory (TD-DFT).

    AB - New ferrocenyl-subtituted compounds containing two different central cores (isocyanurate and 1,3,5-phenylene) and extended by two kinds of branches bearing both vinyl ferrocenyl (1 and 3) and cross-conjugated ferrocenyl-chalcone (2, 4 and 5) as endgroups have been synthetized and characterized both spectroscopically and electrochemically. These molecules have been synthesized in order to investigate the electronic properties imparted by both types of branches when they are connected to the central core. For all compounds, electrochemical studies have showed a simultaneous oxidation of all ferrocene units present in each compound. For all of them, except for compound 2, a chemically reversible oxidation wave on the voltammograms has been observed. In contrast, for compound 2, a chemically irreversible oxidation wave is obtained. Moreover, the vinyl ferrocenyl derivatives have presented a lower redox peak potential with respect to ferrocene standard compound, and the ferrocenyl-chalcone bearing derivatives, in accordance with a change in the electron releasing capability of these endgroups, have been oxidized at a higher potential. Bathochromic shifts of the active transitions in Uv-Vis region have been observed, which are associated to the presence of carbonyl groups in those molecular structures containing it. These results are in agreement with theoretically calculated transition energies, which have been obtained for compounds 1 and 2 using Time Dependent Density Functional Theory (TD-DFT).

    KW - Cyclic voltammetry

    KW - Redox-active ferrocenyl-based compounds

    KW - Time-dependent DFT

    KW - Uv-Vis absorption

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    U2 - 10.1016/j.ica.2018.10.038

    DO - 10.1016/j.ica.2018.10.038

    M3 - Article

    VL - 486

    SP - 95

    EP - 100

    JO - Inorganica Chimica Acta

    T2 - Inorganica Chimica Acta

    JF - Inorganica Chimica Acta

    SN - 0020-1693

    ER -