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, 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.

A Dual Electrochrome of Poly‐(3,4‐Ethylenedioxythiophene) Doped by N,N′‐Bis(3‐sulfonatopropyl)‐4‐4′‐bipyridinium—Redox Chemistry and Electrochromism in Flexible Devices

“…[7][8][9] Ko et al [10] associated an electrochromic viologen with EDOT; however, the route of derivatizing the monomer and its further polymerization are rather complicated processes. Similarly, post-polymerization functionalization of PEDOT has also been done [11] but there is a paucity of reports wherein electrochromic efficiency of such derivatized polymers has been studied.…”

A versatile route to polythiophenes with functional pendant groups using alkyne chemistry

“…Thus, the hydroxylmethyl derivative EDOT-CH 2 OH [16], aminomethyl derivative EDOT-CH 2 NH 2 [17] and the methylenethiol derivative EDOT-CH 2 SH [18], as nucleophiles, as well as the halomethyl derivative EDOT-CH 2 -Cl/Br [6,9] and the exomethylene-EDOT [19] as electrophiles, can be used to form ether, thioether, ester, amine and peptide linkages with the pendant groups. The polar reaction conditions required for their synthesis exclude the use of pendant groups featuring electrophilic or nucleophilic functional moieties, such as esters and alkyl halide, or alcohols and phenols.…”

Electrochromic pattern formation by photo cross-linking reaction of PEDOT side chains

“…2-Chloromethyl-2,3-dihydrothieno [3,4-b] [1,4]dioxine (CMEDOT) was synthesized according to the method reported in the literature. 23 2-((2,3-Dihydrothieno[3,4-b] [1,4]dioxin-2-yl)methoxy) Ethyl Methacrylate (EDOT-EMA). To two necked 50 mL flask equipped with N 2 purge was added CMEDOT (0.5 g, 2.6 mmol), 2-hydroxyethyl methacrylate (HEMA, 0.338 g, 2.6 mmol), K 2 CO 3 (3.6 g, 26 mmol) and 30 mL of dry DMF.…”