Synthesis and Electronic Properties of Anthraquinone-, Tetracyanoanthraquinodimethane-, and Perylenetetracarboxylic Diimide-Functionalized Poly(3,4-ethylenedioxythiophenes)

Abstract

Poly(3,4-ethylenedioxythiophene) (PEDOT) is frequently used as a conducting layer in various applications, e.g., organic devices. However, the modification of the precursor 3,4-ethylenedioxythiophene (EDOT) has only very recently received some attention. Here, we report the efficient synthesis of chloromethyl-functionalized EDOT 3 which is a versatile intermediate to easily access functionalized EDOT derivatives and their corresponding PEDOTs bearing, e.g., electron acceptor groups. In this respect, novel EDOT derivatives 11 − 13 covalently functionalized with 9,10-anthraquinone (AQ), perylenetetracarboxylic diimide (PTCDI), and 11,11,12,12-tetracyano-9,10-anthraquinodimethane (TCAQ) have been synthesized and potentiodynamically electropolymerized. The redox properties of the new polymers P11 − P13 were investigated, indicating that in the hybrid systems, both the PEDOT backbone and the acceptor moieties basically retain their individual properties. In the same line, optical spectra reveal the superimposition of the optical transitions of the individual π-systems.