Fused Tetrathiafulvalene and Benzoquinone Triads: Organic Positive-Electrode Materials Based on a Dual Redox System

Yohji Misaki; Shigenobu Noda; Minami Kato; Tomokazu Yamauchi; Toko Oshima; Aya Yoshimura; Takashi Shirahata; Masaru Yao

doi:10.1002/cssc.202000178

Fused Tetrathiafulvalene and Benzoquinone Triads: Organic Positive-Electrode Materials Based on a Dual Redox System

ChemSusChem. 2020 May 8;13(9):2312-2320. doi: 10.1002/cssc.202000178. Epub 2020 Apr 24.

Authors

Yohji Misaki^{1

2

3}, Shigenobu Noda¹, Minami Kato¹, Tomokazu Yamauchi¹, Toko Oshima¹, Aya Yoshimura^{1

3}, Takashi Shirahata^{1

2

3}, Masaru Yao⁴

Affiliations

¹ Department of Applied Chemistry, Graduate School of Science and Engineering, Ehime University, 3 Bunkyo-cho, Matsuyama, 790-8577, Japan.
² Research Unit for Power Generation and Storage Materials, Ehime University, 3 Bunkyo-cho, Matsuyama, 790-8577, Japan.
³ Research Unit for Development of Organic Superconductors, Ehime University, 2-5 Bunkyo-cho, Matsuyama, 790-8577, Japan.
⁴ Research Institute of Electrochemical Energy, National Institute of Advanced Industrial Science and Technology (AIST), 1-8-31 Midorigaoka, Ikeda, Osaka, 563-8577, Japan.

PMID: 32096607
DOI: 10.1002/cssc.202000178

Abstract

Fused donor-acceptor triads composed of two tetrathiafulvalenes (TTFs) and benzoquinone (BQ; 1) or naphthoquinone (NQ; 2) were successfully synthesized. X-ray structure analysis of the bis(n-butylthio) derivative revealed that the molecules are stacked in a head-to-tail manner. The bis(n-hexylthio)-1 exhibited six-pairs of one-electron transfer waves in the cyclic voltammogram, corresponding to the formation of both reduction and oxidation states from -2 to +4. The unsubstituted and bis(methylthio) derivatives of 1 and 2 were active materials in positive electrodes for rechargeable batteries, several of which displayed energy densities exceeding 800 mWh g^-1 . The bis(methylthio)-2 also functions as a positive electrode material for a rechargeable sodium-ion battery.

Keywords: X-ray diffraction; benzoquinone; electrochemistry; rechargeable batteries; tetrathiafulvalene.

Abstract

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