NHC-Terphenyl Radicals and Anions: Tuning Stability and Redox Properties via Substituent Patterning.

ABSTRACT: Herein, we report the influence of C2-terphenyl substitution patterns (i.e., p-terphenyl versus m-terphenyl) on the redox behavior and stability of the corresponding radicals and anions derived from N-heterocyclic carbenes (NHCs). Three well-known NHCs; SIPr (1a), IPr (1b), and Me-IPr (1c) (SIPr = C{N(Dipp)CH₂}₂, IPr = C{N(Dipp)CH}₂; Me-IPr = C{N(Dipp)CCH₃}₂; Dipp = 2,6-iPr₂C₆H₃); were functionalized at the C2 position using 4-bromo-p-terphenyl (p-TerBr) and 5'-bromo-m-terphenyl (m-TerBr) under nickel catalysis, yielding the corresponding cations [(NHC)p-Ter]Br (2a-c) and [(NHC)m-Ter]Br (3a-c), respectively. Cyclic voltammetry (CV) measurements of 2a-c reveal two distinct reversible redox events, while

SUBMITTER: Steffenfauseweh H 

PROVIDER: S-EPMC12707353 | biostudies-literature | 2025 Dec

REPOSITORIES: biostudies-literature