Synthesis and Characterization of Regioregular Water-Soluble 3,4-Propylenedioxythiophene Derivative and Its Application in the Fabrication of High-Contrast Solid-State Electrochromic Devices

Abstract

Water-soluble sulfonated monomer based on 3,4-propylenedioxythiophene (ProDOT-sultone) was synthesized and characterized for the first time via the O-alkylation of the corresponding unreactive β,β-disubstituted hydroxyl group with propane sultone in the presence of a catalytic amount of 1,4-diazabicyclo[2.2.2]octane (DABCO). This new monomer was oxidatively polymerized to produce regioregular water-soluble conjugated anionic polyelectrolyte, which was then used for the fabrication of solid-state electrochromic devices using the layer-by-layer (LbL) deposition method. These solid-state devices were found to exhibit better electrochromic properties in terms of color contrast, switching time, coloration efficiency (CE), surface control electroactivity, and conductivity in thin films compared with the corresponding water-soluble regiorandom 3,4-ethylenedioxythiophene (EDOT) derivative. For the 40 and 80 bilayer solid-state electrochromic devices, the electrochemical contrast was observed to be 31 and 40% at 570 nm with fast solid-state switching times of 100 and 220 ms, respectively, indicating faster movement of the ions in and out of the films. Furthermore, the CE was found to be as high as 250 cm 2 /C for the 80 bilayer device and was independent of the device thickness, indicating the full accessibility of all of the ionic sites, even in thicker films. Four-point probe conductivity of the LbL and in situ conductivity of solution cast films were found to be in the range of 10 -4 and 10 -3 S/cm, respectively.

Self‐Doped Conjugated Polymeric Nanoassembly by Simplified Process for Optical Cancer Theragnosis

“…The chemical structure of PPDS nanoassembly was confirmed using Fourier‐transform infrared (FT‐IR) spectroscopy (Figure S2 and Table S1, Supporting Information). The SO stretching of the sultone and the CC stretching frequency of the conjugated polymer from PPDS were observed at 1191 and 1537 cm −1 , respectively . Moreover, due to the outer sultone groups of PPDS nanoassembly (Figure e), the zeta‐potential was −29.6 ± 7.3 mV and the successful synthesis of redox active PPDS was confirmed with a cyclic voltammogram in an electrochemical study as shown in Figure c.…”

Polythiophene-based conjugated polyelectrolyte: Optical properties and association behavior in solution

“…These materials have attracted a lot of interest in the last decades because of wide range of potential applications such as fluorescence sensors for biomolecules [1], active layers in light emitting diodes [2], active components in electrochromic devices [3], or active components in photovoltaic cells [4,5]. In spite of such interest, the studies of solution properties are surprisingly rare although it is known that aggregates present in the solution can be transferred into the solid state.…”

Optical, Electrochemical, and Structural Properties of Spray Coated Dihexyl Substituted Poly (3,4 Propylene Dioxythiophene) Film for Optoelectronics Devices

“…This is attributed to provide the faster movement of the ions on the polymer film at higher scan rate that is required for fast electrochromic switching [22]. At room temperature, the diffusion coefficient was calculated as 0.019 × 10 -5 cm 2 /sec at 150 mV/s [23].…”