One-step synthesis of 1,3- and 1,1′-diarylated ferrocenes toward main-chain metallomacrocycles

Abstract

An efficient one-step synthesis of 1,3- and 1,1′-diarylferrocenes was developed via the reaction of ferrocene with anilines. This practical method enables gram-scale preparation of diarylsubstituted ferrocene derivatives. Furthermore, the 1,1′-diarylferrocene served as a key building block for the concise construction of a main-chain ferrocene-based macrocycle (main-Fc[11]CPP) in only two additional steps. The structure of main-Fc[11]CPP was unambiguously confirmed by single-crystal X-ray diffraction, revealing a strained ellipsoidal geometry. Photophysical and electrochemical studies demonstrate that the macrocycle exhibits intramolecular charge-transfer behavior and possesses a lower strain energy compared to its side-chain analog.