Synthesis and Properties of a Novel Through-Space Conjugated Polymer with [2.2]Paracyclophane and Ferrocene in the Main Chain

Abstract

The novel conjugated polymer (12) which has [2.2]paracyclophane and ferrocene units in the polymer backbone was synthesized by palladium-catalyzed polycondensation of the monomer (10) with diiodoferrocene (11). The obtained polymer (12) was soluble in common organic solvents, and the structure of 12 was confirmed by 1H NMR, 13C NMR, and FT-IR. The polymer showed delocalization of the π-electron via the through-space of the [2.2]paracyclophane moiety. The [2.2]paracyclophane unit was more effective for the delocalization of the π-electron than the ferrocene unit. The cyclic voltammetry measurement of 12 showed a broad oxidation potential reversibly with a Epa value of 0.62 V. The electrochemical oxidation was diffusion-controlled by the linear dependence of the oxidative peak currents (I) on the square root of the scan rate (υ1/2), and the diffusion coefficient (D) of the electroactive substance was about 5.5 × 10-7 (cm2/s). On iodine doping under ambient conditions, the polymer (12) showed a maximum conductivity of 1.6 × 10-4 S/cm.