The synthesis and electrochemical behavior of 1,4-di-(2,5-dimethylazaferrocenyl)-1,3-butadiyne

Rigid-rod ferrocene capped alkynes have attracted a lot of attention recently. In this note we report an efficient synthesis of the 1,4-di-(2,5-dimethylazaferrocenyl)-1,3-butadiyne which is the first known azaferrocene capped diacetylene derivative. The cyclic voltammetry measurements at different scan rates and temperatures indicate good electronic communication between two iron centers. Better shaped reduction peaks at higher scan rates in 22 °C and −40 °C can point to increased stability of the monocation.

The title compound (4) was prepared by oxidative homocoupling of 1′-ethynyl-2,5-dimethylazaferrocene. The cyclic voltammetry measurements of 4 were made within the scan rate range 0.1–2 V/s of two temperatures: −40 °C and 22 °C and indicate electronic communication between two iron centers.Figure optionsDownload as PowerPoint slide