Issue 8, 2018

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

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

Supplementary files

Article information

Article type
Paper
Submitted
15 Febr. 2018
Accepted
23 Febr. 2018
First published
28 Febr. 2018

New J. Chem., 2018,42, 6101-6113

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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