Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 8, Pages 5680-5689Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c00165
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- University of Rome Tor Vergata
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This paper presents a detailed investigation of the redox behavior of KuQuinones, emphasizing the unique nature of these molecules and the significant shifts in redox potential caused by changes in experimental parameters.UV-vis-NIR spectroelectrochemical experiments and DFT calculations are discussed to clarify the nature of the reduced species in solution.
The study of the electrochemical properties of variegated quinones is a fascinating topic in chemistry. In fact, redox reactions occurring with quinoid scaffolds are essential for most of their applications in biological systems, in photoelectrochemical devices, and in many other fields. In this paper, a detailed investigation of KuQuinones' redox behavior is presented. The distinctiveness of such molecules is the presence in the structure of two condensed naphthoquinone units, which implies the possibility to undergo multiple one-electron reduction processes. Solvent, supporting electrolyte, and hydrogen bond donor species effects have been elucidated. Changing the experimental parameters provoked significant shift of the redox potential for each reduction process. In particular, additions of 2,2,2-trifluoroethanol as a hydrogen bond donor in solution as well as Lewis acid coordination were crucial to obtain important shifts of the redox potentials toward more favorable values. UV-vis-NIR spectroelectrochemical experiments and DFT calculations are also presented to clarify the nature of the reduced species in solution.
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