Electro-Oxidative Polymerization of Aromatic Monomers without an Electric Power Supply

Abstract

Electrochemistry is a powerful tool for organic synthesis based on electron transfer-driven reactions at the substrate/electrode interface. The use of electricity for synthetic reactions without the need for hazardous chemical oxidants and reductants is recognized as a green and sustainable approach. We have recently developed a split bipolar electrode (s-BPE) system [1], in which the redox reactions can be driven in a low electrolyte concentration, with batch [2,3] and flow [4] cells. Herein, we report a novel s-BPE system for organic electrosynthesis driven under a streaming potential condition with a pressure flow. As a proof-of-concept study on electrosynthesis without an electric power supply, electrochemical oxidative polymerization of aromatic monomers such as pyrrole successfully yielded the corresponding polymer films on an electrode surface at the upstream, which acted as an anode [5].[1] Shida, N.; Zhou, Y.; Inagi, S. Chem. Res. 2019, 52, 2598-2608.[2] Miyamoto, K.; Nishiyama, H.; Tomita, I.; Inagi, S. ChemElectroChem 2019, 6, 97-100.[3] Shida, N.; Villani, E.; Sanuki, M.; Miyamoto, K.; Gotou, A.; Isogai, I.; Yamauchi, A.; Fuchigami, T.; Tomita, I.; Inagi, S. Electrochemistry, 2021, 89, 476-479.[4] Sakagami, H.; Takenaka, H.; Iwai, S.; Shida, N.; Villani, E.; Gotou, A.; Isogai, T.; Yamauchi, A.; Kishikawa, Y.; Fuchigami, T.; Tomita, I.; Inagi, S. ChemElectroChem, 2022, 9, e202200084[5] Iwai, S.; Suzuki, T.; Sakagami, H. Miyamoto, K.; Chen, Z.; Konishi, M.; Villani, E.; Shida, N.; Tomita, I.; Inagi, S. Commun. Chem., 2022, 5, 66.