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Issue 8, 2018
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Ferrocene amphiphilic D–π–A dyes: synthesis, redox behavior and determination of band gaps

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Abstract

We report the synthesis of a series of ferrocene amphiphilic donor–π–acceptor dyes, with the general formula (Fc-CH[double bond, length as m-dash]CH-HetNC16H33)+ X [where: Fc behaves as the donor group, a double bond as the π bridge, and 2-,4-pyridinium and 4-quinolinium as the potent acceptor groups (2a–b and 4, X = Br or BF4)], in good overall yields. Together with their neutral counterparts (6a–b and 7), the photophysical and electrochemical properties of these compounds were investigated by means of UV-Vis spectroscopy and cyclic voltammetry. The optical and electrochemical band gaps of these dyes were calculated, which indicated that 4 has the lowest bandgap value. Time-dependent DFT calculations indicate that the lowest energy absorption band displayed for these compounds has mainly metal-to-ligand charge transfer character, with the HOMO–LUMO electronic transition being the main contribution.

Graphical abstract: Ferrocene amphiphilic D–π–A dyes: synthesis, redox behavior and determination of band gaps

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The article was received on 15 Feb 2018, accepted on 23 Feb 2018 and first published on 28 Feb 2018


Article type: Paper
DOI: 10.1039/C8NJ00787J
Citation: New J. Chem., 2018,42, 6101-6113
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    Ferrocene amphiphilic D–π–A dyes: synthesis, redox behavior and determination of band gaps

    B. López-Mayorga, C. I. Sandoval-Chávez, P. Carreón-Castro, V. M. Ugalde-Saldívar, F. Cortés-Guzmán, J. G. López-Cortés and M. C. Ortega-Alfaro, New J. Chem., 2018, 42, 6101
    DOI: 10.1039/C8NJ00787J

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