Login / Signup

Disclosing Cyclic(Alkyl)(Amino)Carbenes as One-Electron Reductants: Synthesis of Acyclic(Amino)(Aryl)Carbene-Based Kekulé Diradicaloids.

Avijit MaitiBenedict J ElversSachinath BeraFelix LindlIvo KrummenacherPrasanta GhoshHolger BraunschweigCem B YildizCarola SchulzkeAnukul Jana
Published in: Chemistry (Weinheim an der Bergstrasse, Germany) (2022)
Herein, we disclose cyclic(alkyl)(amino)carbenes (CAACs) to be one-electron reductants under the formation of a transient radical cation as indicated by EPR spectroscopy. The disclosed CAAC reducing reactivity was used to synthesize acyclic(amino)(aryl)carbene-based Thiele and Chichibabin hydrocarbons, a new class of Kekulé diradicaloids. The results demonstrate CAACs to be potent organic reductants. Notably, the acyclic(amino)(aryl)carbene-based Chichibabin's hydrocarbon shows an appreciable population of the triplet state at room temperature, as evidenced by both variable-temperature NMR and EPR spectroscopy.
Keyphrases
  • ionic liquid
  • room temperature
  • high resolution
  • solid state
  • single molecule
  • magnetic resonance
  • blood brain barrier
  • quantum dots
  • electron transfer
  • subarachnoid hemorrhage
  • water soluble
  • energy transfer