Synthesis and Electrochemical Properties of 2-[4-(2-Methacryloyl)-piperazine-1-ylmethyl]-9Н-thioxanthen-9-one-S,S-dioxide and Its Copolymer with Methyl Methacrylate
D. S. ODINTSOV, I. G. IRTEGOVA, I. A. OS’KINA, I. K. SHUNDRINA, L. A. SHUNDRIN
Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Novosibirsk, Russia
Keywords: thioxanthenone, radical copolymerization, electrochemical reduction, cyclic voltammetry, electron traps, memristor
Abstract
2-[4-(2-Methacryloyl)-piperazine-1-ylmethyl]-9 H -thioxanthen-9-one-S,S-dioxide 1, an electrochemically active monomer, has been synthesised from 2-(piperazine-1-ylmethyl)-9 Н -thioxanthen-9-one-S,S-dioxide and methacryloyl chloride. Subsequent radical copolymerisation of the synthesised compound with methylmethacrylate leads to an electroactive copolymer (PMMA-co-ThxSO2) with the ratio of methyl methacrylate fragments in the chain to the pendant (side) groups of the 9 Н -thioxanthen-9-one S,S-dioxide structure equal to 95 : 5, respectively. It has been shown by cyclic voltammetry that the electrochemical reduction (ECR) of 1 in acetonitrile (MeCN) is a two-electron and two-stage process, with the formation of long-living radical anion at the first one-electron stage and unstable dianion at the second stage. Electrochemical reduction of PMMA-co-ThxSO2 is due to the reductive electrochemical activity of the pendant groups, and its mechanism is similar to the ECR of monomer 1. This compound is a polymer with pendant groups that play the role of efficient electron traps during charge transport inside the thin copolymer film, and it can be used in the resistive memory technologies (ReRAM - Resistive Random Access Memory) as the active working layer of memristors.
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