Electrocatalytic hydrogen production using [FeFe]-hydrogenase mimics based on tetracene derivatives

Motonori Watanabe; Kenta Goto; Takaaki Miyazaki; Masahiko Shibahara; Yuan Jay Chang; Tahsin J. Chow; Tatsumi Ishihara

doi:10.1039/C9NJ02790D

Electrocatalytic hydrogen production using [FeFe]-hydrogenase mimics based on tetracene derivatives†

Motonori Watanabe,

*^a Kenta Goto,^b Takaaki Miyazaki,

^c Masahiko Shibahara,^d Yuan Jay Chang,

^e Tahsin J. Chow^e and Tatsumi Ishihara

^af

Author affiliations

* Corresponding authors

^a International Institute for Carbon-Energy Research (I2CNER), Kyushu University, Motooka 744, Nishi-ku, Fukuoka 819-0385, Japan
E-mail: mwata@i2cner.kyushu-u.ac.jp

^b Institute for Materials Chemistry and Engineering, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka 819-0395, Japan

^c Department of Chemistry and Biochemistry, Graduate School of Engineering, 744 Motooka Nishi-ku, Fukuoka 819-0395, Japan

^d Division of Natural Sciences, Faculty of Science and Technology, Oita University, Dannoharu 700, Oita, Japan

^e Department of Chemistry, Tunghai University, Taichung, Taiwan

^f Department of Applied Chemistry, Faculty of Engineering, Kyushu University, Nishi-ku, Fukuoka 819-0395, Japan

Abstract

The synthesis, structure, physical properties, and electrocatalytic hydrogen production of tetrathiatetracene ligand based [FeFe]-hydrogenase mimic molecules were investigated. By adjusting the amount of iron, mono- and bis-[FeFe] coordinated complexes 1 and 2 were synthesized. The structures of 1 and 2 were analysed by NMR, IR, and absorption spectroscopies, and cyclic voltammetry and DFT computational analysis. In the DFT electron density maps, the HOMOs and LUMOs were located at tetrathiatetracene units, indicating that these complexes retain mainly acene characteristics. When weak acid Et₃NHBF₄ was added to CH₂Cl₂ solutions of 1 or 2, the reduction potential of iron complexes was shifted to more positive values proportional to the concentration of acid. As the acid concentration increased, the current of the reduction wave also increased, indicating the occurrence of a catalytic proton reduction reaction. The bulk electrolysis reaction showed 65.8 TON for 1 and 52.8 TON for 2.

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Article information

DOI: https://doi.org/10.1039/C9NJ02790D
Article type: Paper
Submitted: 29 May 2019
Accepted: 05 Aug 2019
First published: 06 Aug 2019

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New J. Chem., 2019,43, 13810-13815

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Electrocatalytic hydrogen production using [FeFe]-hydrogenase mimics based on tetracene derivatives

M. Watanabe, K. Goto, T. Miyazaki, M. Shibahara, Y. J. Chang, T. J. Chow and T. Ishihara, New J. Chem., 2019, 43, 13810 DOI: 10.1039/C9NJ02790D

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New Journal of Chemistry

Electrocatalytic hydrogen production using [FeFe]-hydrogenase mimics based on tetracene derivatives†

Abstract

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Electrocatalytic hydrogen production using [FeFe]-hydrogenase mimics based on tetracene derivatives

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