Synthesis and Characterization of a Triphenyl‐Substituted Radical and an Unprecedented Formation of a Carbene‐Functionalized Quinodimethane

Authors:
Publisher website
Google Scholar
Abstract
The trichlorosilylcarbene monoradical (CycAAC)SiCl3 (1) was directly converted to (CycAAC)SiPh3 (2) by substitution of the three chlorine atoms with phenyl groups without affecting the radical center adjacent to the silicon atom. In addition to the structure determination, compound 2 was studied by EPR spectroscopy and DFT calculations. The three hyperfine lines in the EPR spectrum of 2 are due to the coupling with 14N nucleus. Functionalized 1,4‐quinodimethane Me2cAACC6H4CPh2 (7) was isolated, whereas carbon analogue of radical 2 was targeted. Cyclic voltammogram of 7 indicated that a stable radical‐anion 7, as well as a radical‐cation 7, can be prepared. Theoretical calculations showed that one‐electron ionization energy and electron affinity of 7 are 5.1 and 0.7 eV mol−1, respectively.

This publication has 38 references indexed in Scilit: