Air-Stable Tetrazene Radical Cation Salts: Structural Requirements and Oxidation Catalysts
Ayari Oshiro, Yusuke Sasano, Shu Saito, Yasuyuki Araki, Soichiro Sugiyama, Eunsang Kwon, Shinji Kajimoto, Yuse Kuriyama, Shohei Yoshinaga, Masaya Takahashi, Katsuhiko Sato, Naoki Shida, Yusuke Ishigaki, Mahito Atobe, Yoshiharu Iwabuchi
TL;DR
Scientists created a new stable radical cation salt that can be used as an efficient catalyst for alcohol oxidation under mild conditions.
Contribution
The first synthesis and characterization of air-stable tetrazene radical cation salts with high catalytic activity.
Findings
The radical cation from DAD is air-stable for over 120 days at room temperature.
X-ray and ESR studies showed electron delocalization in the tetrazene core and adamantane framework.
DAD exhibits two reversible redox processes and efficient catalytic activity for alcohol oxidation.
Abstract
In this study, stable tetrazene radical cation salts were synthesized and characterized for the first time. The radical cation derived from 1,2-di(2-azaadamantan-2-yl)diazene (DAD) was isolated as an air-stable solid, retaining its integrity for at least 120 days at ambient temperature (∼25 °C) and pressure. X-ray crystallography and electron spin-resonance spectroscopy revealed the delocalization of the unpaired electron over the tetrazene core and into the adamantane framework. DAD undergoes two well-separated, reversible redox processes and displays high catalytic activity for alcohol oxidation under mild conditions. Systematic structural modifications identified the key framework features governing the radical cation stability and catalytic performance.
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Taxonomy
TopicsOxidative Organic Chemistry Reactions · Radical Photochemical Reactions · Covalent Organic Framework Applications