Poly(3,4-ethylenedioxypyrrole):  Organic Electrochemistry of a Highly Stable Electrochromic Polymer

Gaupp, Carleton L.; Zong, Kyukwan; Schottland, Philippe; Thompson, Barry C.; Thomas, Christopher A.; Reynolds, John R.

doi:10.1021/ma9916180

Cited by 119 publications

(94 citation statements)

References 17 publications

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“…The original route, labeled as Route A, was pioneered by the groundbreaking work of Merz et al [32,33] and later expanded upon in our group. [34][35][36][37] This route closely resembles that of an old, well-exploited route towards 3,4-dioxythiophene derivatives. [38] Route A begins with diester 1, which is ring-closed to the 3,4-dihydroxypyrrole derivative 2 via a Hinsberg condensation with diethyl oxalate.…”

Section: Synthesis Of Xdop Monomersmentioning

confidence: 56%

“…Table 1 illustrates the various structure-property relationships of the monomers from Scheme 2 and their respective polymers. It can be seen that the monomer oxidation potential (E p,m ) of most of the N-hydro monomers [35,37] is found between 0.95-1.20 V versus SCE (one notable exception is DMOP, with an E p,m of 0.84 V [32,43] ), whereas the N-alkylated derivatives [32,44] possess a monomer oxidation potential that is almost 200 mV lower. This phenomenon can be attributed to the N-alkyl group donating electron density into the p-system, raising the HOMO with respect to its N-hydro derivative.…”

Section: Pxdop Synthesismentioning

confidence: 99%

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Poly(3,4‐alkylenedioxypyrroles): The PXDOPs as Versatile Yet Underutilized Electroactive and Conducting Polymers

2006

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The poly(3,4‐dioxypyrrole) (PXDOP) family of conducting and electroactive polymers has now been developed to the point that multiple synthetic routes allow many functionalized polymers with controllable optoelectronic and redox properties. These properties, which include high conductivity, multicolor cathodic and anodic electrochromism, and rapid redox switching, allow these materials to be used in a variety of applications that potentially include conducting coatings, electrochromic windows and displays, chemical sensors, bioactive materials, and mechanical actuators. Surprisingly, the scientific literature published on the PXDOP derivatives has been isolated and sparse compared to that of other conducting polymers. This report will highlight the synthesis and materials properties of PXDOPs and show how these powerful materials fit into the frontier of conducting polymers research.

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Section: Synthesis Of Xdop Monomersmentioning

confidence: 56%

Section: Pxdop Synthesismentioning

confidence: 99%

Poly(3,4‐alkylenedioxypyrroles): The PXDOPs as Versatile Yet Underutilized Electroactive and Conducting Polymers

2006

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“…Rapidly switchable electrochromic polymers are based on new poly(3,4-alkylenedioxy-thiophene) derivatives. [68] A Reynolds review summarizes the developments of his group's work. [69] A solid state electrochromic device based on two optically complementary conducting polymers has been made.…”

Section: Electroactive Polymersmentioning

confidence: 99%

Electrochromic Systems and the Prospects for Devices

2001

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Many inorganic and organic materials exhibit redox states with distinct electronic (UV‐vis) absorption bands. When the switching of redox states generates new or different visible region bands, the material is electrochromic. Electrochromic materials are currently attracting much interest in academia and industry for both their fascinating spectroelectrochemical properties and their commercial applications. In this review some of the most important examples from the major classes of electrochromic materials are highlighted. Examples of their use in both prototype and commercial electrochromic devices are illustrated including car mirrors, windows and sun‐roofs of cars, windows of buildings, displays (see Figure), printing, and frozen‐food monitoring.

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“…Electrochemical polymerization is a widely used technique to produce electrochromic materials [1][2][3][4]. Electric field is applied between an anode and a cathode in an electrolyte containing a monomer for performing electrochemical polymerization.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of electro-optically active polymer composite of poly[2,2'-bis(3,4-ethylenedioxythiophene)-alt-fluorene]/hydroxypropyl cellulose showing liquid crystal structure

Eguchi¹,

Kawabata²,

Goto³

2017

Express Polym. Lett.

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Abstract. Electrochemical preparation of a composite consisting of poly[2,2′-bis(3,4-ethylenedioxythiophene)-alt-fluorene] and hydroxypropyl cellulose (PEFE/HPC) was carried out. We conducted electrochemical polymerization of poly[2,2′-bis(3,4-ethylenedioxythiophene)-alt-fluorene] (EFE) as a monomer in a lyotropic liquid crystal of HPC. We used an organic solvent instead of water for lyotropic liquid crystal medium to expand the possibility of the range of monomers, although water is usually employed as a solvent for HPC for showing liquid crystallinity. Here, we employed N,N-dimethylformamide (DMF) as a solvent for HPC. Electrochemical polymerization in the polymer liquid crystal was carried out to obtain a polymer film with liquid crystal order. The polymer film thus prepared exhibited optical activity. Fourier transfer infrared (FT-IR) absorption spectroscopy reveals that the film is a composite consisting of HPC and polymer. The composite PEFE/HPC thus prepared in HPC/DMF system showed electrochromism.

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Poly(3,4-ethylenedioxypyrrole): Organic Electrochemistry of a Highly Stable Electrochromic Polymer

Cited by 119 publications

References 17 publications

Poly(3,4‐alkylenedioxypyrroles): The PXDOPs as Versatile Yet Underutilized Electroactive and Conducting Polymers

Poly(3,4‐alkylenedioxypyrroles): The PXDOPs as Versatile Yet Underutilized Electroactive and Conducting Polymers

Electrochromic Systems and the Prospects for Devices

Synthesis of electro-optically active polymer composite of poly[2,2'-bis(3,4-ethylenedioxythiophene)-alt-fluorene]/hydroxypropyl cellulose showing liquid crystal structure

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