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Article

Voltammetry and Spectroelectrochemistry of TCNQ in Acetonitrile/RTIL Mixtures

Chemistry Department, Marquette University, P.O. Box 1881, Milwaukee, WI 53092, USA
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Author to whom correspondence should be addressed.
Academic Editor: Luísa Margarida Martins
Molecules 2020, 25(2), 303; https://doi.org/10.3390/molecules25020303
Received: 13 November 2019 / Revised: 30 December 2019 / Accepted: 4 January 2020 / Published: 12 January 2020
(This article belongs to the Special Issue Ionic Liquids for Electrochemistry)
Understanding the solvation and ion-pairing interactions of anionic substrates in room-temperature ionic liquids (RTIL) is key for the electrochemical applications of these new classes of solvents. In this work, cyclic voltammetry and visible and infrared spectroelectrochemistry of tetracyanoquinodimethane (TCNQ) was examined in molecular (acetonitrile) and RTIL solvents, as well as mixtures of these solvents. The overall results were consistent with the formation of RTIL/acetonitrile nanodomains. The voltammetry indicated that the first electrogenerated product, TCNQ, was not incorporated into the RTIL nanodomain, while the second electrogenerated product, TCNQ2−, was strongly attracted to the RTIL nanodomain. The visible spectroelectrochemistry was also consistent with these observations. Infrared spectroelectrochemistry showed no discrete ion pairing between the cation and TCNQ in either the acetonitrile or RTIL solutions. Discrete ion pairing was, however, observed in the acetonitrile domain between the tetrabutylammonium ion and TCNQ2−. On the other hand, no discrete ion pairing was observed in BMImPF6 or BMImBF4 solutions with TCNQ2−. In BMImNTf2, however, discrete ion pairs were formed with BMIm+ and TCNQ2−. Density function theory (DFT) calculations showed that the cations paired above and below the aromatic ring. The results of this work support the understanding of the redox chemistry in RTIL solutions. View Full-Text
Keywords: TCNQ; voltammetry; spectroelectrochemistry; ion pairs; RTIL nanodomains TCNQ; voltammetry; spectroelectrochemistry; ion pairs; RTIL nanodomains
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MDPI and ACS Style

Atifi, A.; Ryan, M.D. Voltammetry and Spectroelectrochemistry of TCNQ in Acetonitrile/RTIL Mixtures. Molecules 2020, 25, 303. https://doi.org/10.3390/molecules25020303

AMA Style

Atifi A, Ryan MD. Voltammetry and Spectroelectrochemistry of TCNQ in Acetonitrile/RTIL Mixtures. Molecules. 2020; 25(2):303. https://doi.org/10.3390/molecules25020303

Chicago/Turabian Style

Atifi, Abderrahman, and Michael D. Ryan. 2020. "Voltammetry and Spectroelectrochemistry of TCNQ in Acetonitrile/RTIL Mixtures" Molecules 25, no. 2: 303. https://doi.org/10.3390/molecules25020303

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