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

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 1 H NMR, 13 C 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 E pa 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 (υ 1/2 ), and the diffusion coefficient ( D ) of the electroactive substance was about 5.5 × 10 -7 (cm 2 /s). On iodine doping under ambient conditions, the polymer ( 12 ) showed a maximum conductivity of 1.6 × 10 -4 S/cm.