Benzothiadiazole, hexylthiophen and alkoxy benzene based solution processable copolymer: Effect of the electron withdrawing substituents (fluorine atoms) on electrochemical, optical and electrochromic properties

Xu, Zhen; Du, Haiyan; Yin, Mengjie; Wang, Bozhen; Xie, Yu

doi:10.1016/j.orgel.2018.06.048

Cited by 28 publications

(11 citation statements)

References 37 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The optical properties of B3a-c were also studied in spin-coated thin films (Figure 2). As expected, the ITC peaks are red-shifted compared with those in solution for the agglomeration and enhanced π-π interactions between polymer chains in the solid-state [66,67]. The B3a-c polymers exhibit identical optical band gap values in chloroform solution and thin-films, 2.24 and 2.15 eV, respectively, calculated from the absorption onsets.…”

Section: Synthesis and Characterization Of Pehondtbtsupporting

confidence: 72%

Synthesis and Characterization of a 2,3-Dialkoxynaphthalene-Based Conjugated Copolymer via Direct Arylation Polymerization (DAP) for Organic Electronics

et al. 2020

View full text Add to dashboard Cite

Poly[(5,5’-(2,3-bis(2-ethylhexyloxy)naphthalene-1,4-diyl)bis(thiophene-2,2′-diyl))-alt-(2,1,3-benzothiadiazole-4,7-diyl)] (PEHONDTBT) was synthesized for the first time and through direct arylation polymerization (DAP) for use as p-donor material in organic solar cells. Optimized reaction protocol leads to a donor-acceptor conjugated polymer in good yield, with less structural defects than its analog obtained from Suzuki polycondensation, and with similar or even higher molecular weight than other previously reported polymers based on the 2,3-dialkoxynaphthalene monomer. The batch-to-batch repeatability of the optimized DAP conditions for the synthesis of PEHONDTBT was proved, showing the robustness of the synthetic strategy. The structure of PEHONDTBT was corroborated by NMR, exhibiting good solubility in common organic solvents, good film-forming ability, and thermal stability. PEHONDTBT film presented an absorption band centered at 498 nm, a band gap of 2.15 eV, and HOMO and LUMO energy levels of −5.31 eV and −3.17 eV, respectively. Theoretical calculations were performed to understand the regioselectivity in the synthesis of PEHONDTBT and to rationalize its optoelectronic properties. Bilayer heterojunction organic photovoltaic devices with PEHONDTBT as the donor layer were fabricated to test their photovoltaic performance, affording low power-conversion efficiency in the preliminary studies.

show abstract

Section: Synthesis and Characterization Of Pehondtbtsupporting

confidence: 72%

Synthesis and Characterization of a 2,3-Dialkoxynaphthalene-Based Conjugated Copolymer via Direct Arylation Polymerization (DAP) for Organic Electronics

et al. 2020

View full text Add to dashboard Cite

show abstract

Section: Electrochemical Characterizationmentioning

confidence: 99%

“…The results showed that the alternative of donor units can modify the redox properties of the D-A type conjugated polymer effectively. In addition, E HOMO value of three polymers can be calculated by the equation below [32]: We can obtain the highest occupied molecular orbital energy (EHOMO) level of BEDPP, FLDPP, and CADPP were −5.30, −5.20 and −5.18 eV, respectively.…”

Section: Electrochemical Characterizationmentioning

confidence: 99%

“…Through the ultraviolet image of the films, the onset absorption wavelength (λ onset ) of the three polymers of BEDPP, FLDPP, and CADPP were 801, 735, and 720 nm, respectively. According to the following Equations [25,32]:…”

Section: Optical Propertiesmentioning

confidence: 99%

“…These achievements indicated that diketopyrrolopyrrole unit is a promising acceptor for the construction of valuable electrochromic materials with the different donor units [31]. For the donor units, exploiting the inherent planarity and conjugated structure, a benzene ring could bridge the polymer and facilitate the charge transformation [32]. As the redox-active chromophores, the alkyl-substituted fluorene and carbazole were always used as the donor units to build D-A type electrochromic polymers [33].…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Synthesis and Characterization of Novel D-A Type Neutral Blue Electrochromic Polymers Containing Pyrrole[3-c]Pyrrole-1,4-Diketone as the Acceptor Units and the Aromatics Donor Units with Different Planar Structures

et al. 2019

Self Cite

View full text Add to dashboard Cite

Three soluble conjugated polymers, named BEDPP, FLDPP, and CADPP, were prepared through the Suzuki polymerized reaction, and employed benzene (BE), fluorene (FL), and carbazole (CA) as the donor units, respectively. The electron-deficient molecule 2,5-bis-(2-octyldodecyl)-3,6-bis-(5-bromo-thiophene)-pyrrole[3-c]pyrrole-1,4-diketone(DPP) was introduced and used as the acceptor unit. The properties of these three copolymers were studied by a series of detailed characterization analysis, including X-ray photoelectron spectroscopy (XPS), colorimetry, electrochemical measurements, spectroelectrochemistry, kinetics, quantitative calculation, and thermogravimetric (TG) analysis, etc. The results revealed that BEDPP displayed a blue color in the neutral state and a light brown color in the oxidized state, FLDPP exhibited a cyan color in the neutral state and a gray color in the oxidized state, while CADPP displayed pure blue color in the neutral state and a light gray color in the oxidized state. All these polymers possess narrow optical band gaps lower than 1.80 eV and satisfactory thermal stability. The kinetic characterization showed that the optical contrasts (ΔT%) in the near-infrared region were superior to the visible region. The optical contrasts of BEDPP, FLDPP, and CADPP are 41.32%, 42.39%, and 45.95% in the near-infrared region, respectively, which made them a good application prospect in the near-infrared region. Amid the three polymers, CADPP has the highest coloration efficiency (around about 288 cm2·C−1) and fast switching times (0.77 s in the coloring process and 0.52 s in the bleaching process) in the visible region, and the comprehensive performance of CADPP can be comparable to that of the reported D-A (Donor-Acceptor) type blue color polymers. In general, based on the good performances and the stable neutral blue color, the three polymers had profound theoretical significance for the development of electrochromic material and the completion of the RGB (Red, Green, Blue) color space.

show abstract

Fluorinated Oleophilic Electrochromic Copolymer Based on 3‐(N‐Trifluoroacetamido)thiophene and 3,4‐Ethylenedioxythiophene (EDOT)

Wang

Shen

Ma³

et al. 2020

ChemElectroChem

View full text Add to dashboard Cite

A new fluorine-containing monomer 3-(Ntrifluoroacetamido)thiophene (F-TH) was synthesized and characterized for the first time. Its molecular structure was determined by a single-crystal X-ray study. F-TH functions as a building block in electropolymerization with 3,4-ethylenedioxythiophene (EDOT) gives a novel conjugated copolymer P(F-TH:EDOT) subsequently. Compared with the parent homopolymer poly(3,4ethylenedioxythiophene) (PEDOT) film, sponge-like nanoporous P(F-TH:EDOT) film has a slightly larger band gap with a reduced hydrophilic and increased oleophilic surface. Spectroelectrochemical analysis results reveal that P(F-TH:EDOT) exhibits excellent electrochromic performances with higher optical contrast (55%) and much shorter coloring time (0.70 s) than that of PEDOT (43%, 1.54 s). The coloration efficiency value of P(F-TH:EDOT) achieves up to 167.9 cm 2 /C, 55% higher than that of PEDOT (108.1 cm 2 /C). These improved electrochromic properties of P(F-TH:EDOT) are probably related with the enhanced wettability to electrolyte solution.Electrochromic conjugated polymers (ECPs), which can effectively adjust the transmitted and reflected light based on their reversible redox states under small external voltages, have been extensively investigated owing to their potential applications on smart windows and mirrors, displays, thermal control, camouflage and sensors. [1][2][3][4][5][6][7][8] As the most established ECPs, thiophene-based polymers have been extensively investigated due to their significant optical changes between redox states, outstanding coloration efficiency and facile switching performances. 9-12 To date, a lot of monomers from the family of thiophenes have been developed as building blocks, and based on them, various ECPs with different properties have been synthesized, [13][14][15][16][17][18] but the

show abstract

Benzothiadiazole, hexylthiophen and alkoxy benzene based solution processable copolymer: Effect of the electron withdrawing substituents (fluorine atoms) on electrochemical, optical and electrochromic properties

Cited by 28 publications

References 37 publications

Synthesis and Characterization of a 2,3-Dialkoxynaphthalene-Based Conjugated Copolymer via Direct Arylation Polymerization (DAP) for Organic Electronics

Synthesis and Characterization of a 2,3-Dialkoxynaphthalene-Based Conjugated Copolymer via Direct Arylation Polymerization (DAP) for Organic Electronics

Synthesis and Characterization of Novel D-A Type Neutral Blue Electrochromic Polymers Containing Pyrrole[3-c]Pyrrole-1,4-Diketone as the Acceptor Units and the Aromatics Donor Units with Different Planar Structures

Fluorinated Oleophilic Electrochromic Copolymer Based on 3‐(N‐Trifluoroacetamido)thiophene and 3,4‐Ethylenedioxythiophene (EDOT)

Contact Info

Product

Resources

About