The Effect of Reduction Potential on the Generation of the Perylene Diimide Radical Anions
- Authors: Zhao Y.Z.1, Li K.X.1, Ding S.Y.1, Zhu M.1, Ren H.P.1, Ma Q.1, Guo Z.1, Tian S.P.1, Zhang H.Q.2, Miao Z.C.1
-
Affiliations:
- School of Sciences, Xijing University
- State Key Laboratory of Metastable Materials Science and Technology, Yanshan University
- Issue: Vol 92, No 7 (2018)
- Pages: 1261-1265
- Section: Chemical Kinetics and Catalysis
- URL: https://journals.rcsi.science/0036-0244/article/view/170045
- DOI: https://doi.org/10.1134/S003602441807035X
- ID: 170045
Cite item
Abstract
Perylene diimide derivatives (PDIs) with different substituents in the bay positions (Un-PDI, DFPDI and THBPDI) were chosen in this report to investigate the effect of potential on the reduction of PDIs through base (hydrazine, 1,2-ethanediamine and triethylamine)-driven keto-enol anion tautomerism. The reduction potentials (PDI/PDI•–) of these compounds determined via cyclic voltammetry are –0.51, ‒0.34, and –0.098 V for Un-PDI, DFPDI, and THBPDI, respectively. The reduction of Un-PDI, DFPDI and THBPDI by hydrazine can produce corresponding radical anions and dianions, but the volume of hydrazine added at which the radicals started to appear is different and depends on their reduction potential. The similar phenomenon was observed using 1,2-ethylenediamine and triethylamine. However, only the radical anion was obtained even in a large excess of 1,2-ethanediamine or triethylamine. Moreover, the reduction of these PDIs with different bases added in the same amount was investigated, and the correlation with their basicity was shown.
About the authors
Y. Z. Zhao
School of Sciences, Xijing University
Email: miaozongcheng@xijing.edu.cn
China, Xi’an, 710123
K. X. Li
School of Sciences, Xijing University
Email: miaozongcheng@xijing.edu.cn
China, Xi’an, 710123
S. Y. Ding
School of Sciences, Xijing University
Email: miaozongcheng@xijing.edu.cn
China, Xi’an, 710123
M. Zhu
School of Sciences, Xijing University
Email: miaozongcheng@xijing.edu.cn
China, Xi’an, 710123
H. P. Ren
School of Sciences, Xijing University
Email: miaozongcheng@xijing.edu.cn
China, Xi’an, 710123
Q. Ma
School of Sciences, Xijing University
Email: miaozongcheng@xijing.edu.cn
China, Xi’an, 710123
Z. Guo
School of Sciences, Xijing University
Email: miaozongcheng@xijing.edu.cn
China, Xi’an, 710123
S. P. Tian
School of Sciences, Xijing University
Author for correspondence.
Email: tspspirit@163.com
China, Xi’an, 710123
H. Q. Zhang
State Key Laboratory of Metastable Materials Science and Technology, Yanshan University
Author for correspondence.
Email: haiquanzhang@ysu.edu.cn
China, Qinhuangdao, 066004
Z. C. Miao
School of Sciences, Xijing University
Author for correspondence.
Email: miaozongcheng@xijing.edu.cn
China, Xi’an, 710123