Electrochemical Properties and Electrochromism of 6-Aryl-1,3-bis(trimethylsilyl)fulvenes and Their Derivatives

Ryota Tatemura; Mikio Yasutake; Hidenori Kinoshita; Katsukiyo Miura

doi:10.1021/acs.joc.1c02133

Electrochemical Properties and Electrochromism of 6-Aryl-1,3-bis(trimethylsilyl)fulvenes and Their Derivatives

J Org Chem. 2022 Jan 7;87(1):172-183. doi: 10.1021/acs.joc.1c02133. Epub 2021 Dec 16.

Authors

Ryota Tatemura¹, Mikio Yasutake¹, Hidenori Kinoshita¹, Katsukiyo Miura¹

Affiliation

¹ Department of Applied Chemistry, Graduate School of Science and Engineering, Saitama University, 255 Shimo-ohkubo, Sakura-ku, Saitama 338-8570, Japan.

PMID: 34913709
DOI: 10.1021/acs.joc.1c02133

Abstract

In this study, we have disclosed intriguing electrochromic properties of 6-aryl-1,3-bissilylfulvenes. The electrolyte solutions (0.1 M n-Bu₄NClO₄ in acetonitrile or dichloromethane) of some 6-aryl-1,3-bissilylfulvenes showed notable color changes when superimposed negative voltages were applied to the solutions. Investigation of the substituents at position 6 revealed that the solution of 1,3-bissilyl-6-anthracenylfulvene exhibited chromic changes under both applied superimposed negative and positive voltages and exhibited a three-color electrochromism. Electrochromic properties of 1,6-diarylfulvenes derived from 6-aryl-1,3-bissilylfulvenes were also investigated. The aryl group at position 1 also contributed to the electrochromism of fulvenes.