Synthesis and electro-optical properties of new conjugated hybrid polymers from EDOT end-capped dibenzothiophene and dibenzofuran

Lin, Kaiwen; Zhen, Shijie; Ming, Shouli; Xu, Jingkun; Lu, Baoyang

doi:10.1039/c4nj01854k

Cited by 23 publications

(19 citation statements)

References 53 publications

(42 reference statements)

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“…It's worth noting that most electropolymerization systems are limited to organic solvents [11,[20][21][22][23][24], which exhibit some shortcomings such as environmental pollution, insecurity, energy shortage etc. Aqueous solution, as a promising "green" alternative solvent medium to traditional volatile and toxic solvents, is beneficial from a cost, handling, environmentally friendly, and safety point of view.…”

Section: Introductionmentioning

confidence: 99%

Aqueous electrosynthesis of an electrochromic material based water-soluble EDOT-MeNH2 hydrochloride

et al. 2016

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. (2016). Aqueous electrosynthesis of an electrochromic material based water-soluble EDOT-MeNH2 hydrochloride. Synthetic Metals, 211 147-154. Aqueous electrosynthesis of an electrochromic material based watersoluble EDOT-MeNH2 hydrochlorideAbstract 2'-Aminomethyl-3,4-ethylenedioxythiophene (EDOT-MeNH2) showed unsatisfactory results when its polymerization occurred in organic solvent in our previous report. Therefore, a water-soluble EDOT derivative was designed by using hydrochloric modified EDOT-MeNH2 (EDOT-MeNH2·HCl) and electropolymerized in aqueous solution to form the corresponding polymer with excellent electrochromic properties. Moreover, the polymer was systematically explored, including electrochemical, optical properties and structure characterization. Cyclic voltammetry showed low oxidation potential of EDOT-MeNH2·HCl (0.85 V) in aqueous solution, leading to the facile electrodeposition of uniform the polymer film with outstanding electroactivity. Compared with poly(2′-aminomethyl-3,4-ethylenedioxythiophene) (PEDOTMeNH2), poly(2′-aminomethyl-3,4-ethylenedioxythiophene salt) (PEDOT-MeNH3 +A-) revealed higher efficiencies (156 cm2 C-1), lower bandgap (1.68 eV), and faster response time (1.4 s). Satisfactory results implied that salinization can not only change the polymerization system, but also adjust the optical absorption, thereby increase the electrochromic properties.

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Section: Introductionmentioning

confidence: 99%

Aqueous electrosynthesis of an electrochromic material based water-soluble EDOT-MeNH2 hydrochloride

et al. 2016

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“…The onset oxidation potential ( E ox,onset ) of DBT‐3DTh was 1.05 V versus Ag/AgCl, lower than DBF‐3DTh (1.12 V vs. Ag/AgCl), which was caused by smaller overlap integral of oxygen atom compared with sulfur atom in the dibenzo‐five‐membered ring. Deeply, to find the relationship between their structures and properties, all the E ox,onset values of DBT/DBF‐heterocycle hybrid monomers were offered in Table , and all values were detected in the same experimental conditions. Among them, EDOT end‐capped monomers, DBT‐EDOT and DBF‐EDOT, were 0.91 V and 0.95 V versus Ag/AgCl, lower than those of thiophene and alkylthiophene end‐capped monomers.…”

Section: Resultsmentioning

confidence: 99%

“…In particular, electrochemical polymerization of DBT‐3DTh revealed an obvious redox couples without potential shift. To compare the redox peak potentials with structural analog, DBT‐EDOT and DBF‐EDOT exhibited obvious redox peaks at 0.55 to 0.80 V versus Ag/AgCl, lower than those of thiophene and alkylthiophene end‐capped polymers owing to the presence of the strong electron‐donating group of EDOT. Thiophene end‐capped polymers, DBT‐Th and DBF‐Th, displayed reversible peaks with oxidation potentials of 1.35 V and reduction potentials of about 1.10 V versus Ag/AgCl, both values were higher than those of polymers with alkylthiophene as end units and DBT/DBF as inner units.…”

Section: Resultsmentioning

confidence: 99%

“…PDBT, as new materials applied in electrochromic devices, shows good hole‐transporting ability, emission properties, and rigid planarity, which makes it a good candidate for constructing host materials . Given that, a series of EDOT and 3‐alkylthiophenes end‐capped DBT/DBF hybrid electrochromic polymers (Scheme ; PDBT‐EDOT, PDBF‐EDOT, PDBT‐Th, PDBF‐Th, PDBT‐3MeTh, PDBF‐3MeTh, PDBT‐3HexTh, PDBF‐3HexTh) have been researched deeply in our lab on their electrochemical and electrochromic performance . However, their solubility cannot meet the demands in real life.…”

Section: Introductionmentioning

confidence: 99%

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Blue to light gray electrochromic polymers from dodecyl‐derivatized thiophene Bis‐substituted dibenzothiophene/dibenzofuran

Lin

Zhao

Ming

et al. 2015

J. Polym. Sci. Part A: Polym. Chem.

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3-Dodecylthiophene end-capped two monomers: 2,8-bis-(4-dodecyl-thiophen-2-yl)-dibenzothiophene (DBT-3DTh) and 2,8-bis-(4-dodecyl-thiophen-2-yl)-dibenzofuran (DBF-3DTh) were synthesized via Stille coupling reaction. Both monomers exhibited emission peaks at about 400 nm with fluorescence quantum yields ranging from 0.16 to 0.21. The corresponding electroactive polymers poly(2,8-bis-(4-dodecyl-thiophen-2-yl)dibenzothiophene) (PDBT-3DTh) and poly(2,8-bis-(4-dodecylthiophen-2-yl)-dibenzofuran) (PDBF-3DTh) were obtained by electropolymerization method and displayed good electrochemical stability. Both polymers switched between light gray in the neutral state and blue in the oxidized state. Kinetic inves-tigations showed that PDBT-3DTh exhibited a maximum optical contrast (DT %) of 25.23% at 575 nm with the coloration efficiency (CE) of 196 cm 2 C 21 . However, the electrochromic properties of PDBF-3DTh were inferior to PDBT-3DTh. Further detailed discussions with EDOT and 3-alkylthiophenes endcapped DBT/DBF hybrid electrochromic polymers were comparatively studied.

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“…To pander to the fast development of various fields, highly urgent demand is to design and synthesize new molecules used as CP precursors according to the principle of adjustable band gap that affects optical and electrical properties . So far, the CPs based on thiophene units such as bithiophenes, 2‐(thiophen‐2‐yl)furan, dibenzothiophenes, thieno[3,2‐ b ]thiophenes, benzodithiophenes, and cyclopentadithiophenes have been fabricated and constructed various organic electronic and photonic devices.…”

Section: Introductionmentioning

confidence: 99%

High‐quality freestanding flexible poly(5‐(2,3‐dihydrothieno[3,4‐b][1,4]dioxin‐5‐yl)‐1H‐indole) film: Electrosyntheses, characterization, and optical properties

Wang

Zhou

et al. 2018

J of Applied Polymer Sci

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A novel co-monomer 5- (2,3-dihydrothieno[3,4-b] [1,4]dioxin-5-yl)-1H-indole (EDTI), based on the combinations of indole and 3,4-ethylenedioxythiophene (EDOT) groups, was synthesized and electrodeposited into flawless free-standing flexible poly (5-(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-1H-indole) (PEDTI) film by Rui Wang, Guo Ye, Weiqiang Zhou and their colleagues. The colors of as-prepared PEDTI film could switch reversibly from purple to brown during the n-and p-doping. Fluorescence spectral studies revealed PEDTI was good blue-green light emitter with the best emission wavelength 461 nm and 488 nm. These results implied that PEDTI had potential applications for photoelectric devices.46929 Thermal conductivity improvement in electrically insulating silicone rubber composites by the construction of hybrid three-dimensional filler networks with boron nitride and carbon nanotubes 47016 High-quality freestanding flexible poly (5-(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-1H-indole) film: Electrosyntheses, characterization, and optical properties

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Synthesis and electro-optical properties of new conjugated hybrid polymers from EDOT end-capped dibenzothiophene and dibenzofuran

Abstract: Two novel EDOT end-capped dibenzo five-membered ring-heterocycle hybrid polymers were synthesised and their optoelectronic properties were explored.

Cited by 23 publications

References 53 publications

Aqueous electrosynthesis of an electrochromic material based water-soluble EDOT-MeNH2 hydrochloride

Aqueous electrosynthesis of an electrochromic material based water-soluble EDOT-MeNH2 hydrochloride

Blue to light gray electrochromic polymers from dodecyl‐derivatized thiophene Bis‐substituted dibenzothiophene/dibenzofuran

High‐quality freestanding flexible poly(5‐(2,3‐dihydrothieno[3,4‐b][1,4]dioxin‐5‐yl)‐1H‐indole) film: Electrosyntheses, characterization, and optical properties

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