Low band-gap diketopyrrolopyrrole-containing polymers for near infrared electrochromic and photovoltaic applications

Neo, Wei Teng; Ye, Qun; Ong, Wen Jie; Wong, Hoi-Ka; Lin, Tingting; Xu, Jianwei

doi:10.1002/pola.27564

Cited by 30 publications

(23 citation statements)

References 59 publications

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“…The thin films of all the polymers showed quasi-reversible oxidation and reduction waves with the onset oxidation potentials (E ox ) at around 0.4~0.6 V (vs Ag/AgCl) and onset reduction potentials (E red ) at around -1.1 V. The oxidation behavior was similar to the reported DPP-based polymers [15]. The E ox values suggested that the triphenylamine derivatives are stronger donors than the fluorene unit and that the substitution of the methoxy group at the para-position with respect to the nitrogen atom facilitated the oxidation, whereas the cyano group substitution made it more difficult.…”

Section: Optical and Electrochemical Propertiessupporting

confidence: 58%

“…The excellent reversibility was previously reported for the anodic electrochromism of the DPP-thiophene copolymers [13][14][15][16][17][18]. Unfortunately, the DPPbased polymers with the fluorene or triphenylamine donors in this study did not show such a reversible electrochromism in the anodic direction.…”

Section: Switching Timecontrasting

confidence: 43%

“…On the other hand, as compared to the semiconducting applications, the electrochromic properties of the DPP-based polymers have rarely been investigated. Most of the reported electrochromic DPP-based polymers were the copolymers with thiophenebased comonomers, and accordingly, they showed only an anodic electrochromism [13][14][15][16][17][18].…”

Section: Introductionmentioning

confidence: 99%

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Electrochromic Behavior of Donor-Acceptor Polymers Containing Diketopyrrolopyrrole Unit

Michinobu

2017

J. Photopol. Sci. Technol.

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Donor-acceptor polymers composed of the electron-rich fluorene or triphenylamine unit and electron-deficient diketopyrrolopyrrole (DPP) unit were investigated. These polymers showed an intense low-energy visible absorption in their neutral film states. The films of all the polymers displayed both oxidation and reduction waves in their cyclic voltammograms due to their narrow bandgaps. Both the anodic and cathodic electrochromic behaviors were investigated and compared to those of the reported DPPbased polymers. The results were explained by the difference in the comonomer structures. In addition, the switching times during the cathodic electrochromism were reported.

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Section: Optical and Electrochemical Propertiessupporting

confidence: 58%

Section: Switching Timecontrasting

confidence: 43%

Section: Introductionmentioning

confidence: 99%

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Electrochromic Behavior of Donor-Acceptor Polymers Containing Diketopyrrolopyrrole Unit

Michinobu

2017

J. Photopol. Sci. Technol.

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“…[3][4][5][6] To date, blue-, green-, magenta-, redcolored and black EC polymers have been reported. [7][8][9][10] In addition, conjugated polymers that are able to switch reversibly between colored and transparent states in both visible and nearinfrared (NIR) regions by electrochemical means are reported.…”

Section: Introductionmentioning

confidence: 99%

“…Thermogravimetric analysis (TGA) was conducted on a PerkinElmer Pyris Diamond TG instrument from 20 to 800 C at a heating rate of 10 Synthesis of monomers and polymers The solution was degassed with argon for 40 min. Then Pd 2 (dba) 3 (8 mg) and P(o-tol) 3 (30 mg) were added to the solution, followed by degassing and charging with argon several times. The reaction mixture was stirred at 100 C for 72 h. Aer cooling down to 70 C, 10 mL of aqueous solution of sodium diethyldithiocarbamate trihydrate was added to the mixture and the mixture was stirred for 12 hours to remove the residual catalyst.…”

mentioning

confidence: 99%

Visible and near-infrared electrochromic thiophene–diketopyrrolopyrrole polymers

2017

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A series of low bandgap polymers containing thiophene and diketopyrrolopyrrole (DPP) units were synthesized and their electrochromic (EC) properties were investigated. It was found that the ratio (R da ) of thiophene to DPP units correlates to the EC properties, in particular optical contrast (DT) and coloration efficiency (CE) in the visible and near-infrared spectral regions (e.g., 1310 nm). At the wavelength of 1310 nm, the CE of polymer P2 (R da ¼ 3 : 1) and DT of polymer P4 (R da ¼ 4 : 1) reached the high values of 1383 cm 2 C À1 and 81.5%, respectively. Polymer P3 (R da ¼ 3.5 : 1) had a relatively short switching time of 1.24 s from the doped state to neutral state. Colors of polymer films changed reversibly between green or blue (neutral state) and grey (doped state) upon the redox cycling.

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Enhanced Optical Contrast and Switching in Near‐Infrared Electrochromic Devices by Optimizing Conjugated Polymer Oligo(Ethylene Glycol) Sidechain Content and Gel Electrolyte Composition

Pankow,

Kerwin,

Cho

et al. 2023

Adv Funct Materials

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A detailed investigation addressing the effects of functionalizing conjugated polymers with oligo(ethylene glycol) (EGn) sidechains on the performance and polymer‐electrolyte compatibility of electrochromic devices (ECDs) is reported. The electrochemistry for a series of donor‐acceptor copolymers having near‐infrared (NIR)‐optical absorption, where the donor fragment is 3,4‐ethylenedioxythiophene (EDOT) or an EGn functionalized bithiophene (g2T) and the acceptor fragment is diketopyrrolopyrrole (DPP) functionalized with branched alkyl or EGn sidechains, is extensively probed. ECDs are next fabricated and it is found that EGn sidechain incorporation must be finely balanced to promote polymer‐electrolyte compatibility and provide efficient ion exchange. Proper electrolyte‐cation pairing and polymer structural tuning affords a 2x increase in optical contrast (from 12% to 24%) and >60x reduction in switching time (from 20 to 0.3 s). Atomic force microscopy (AFM)/grazing incidence wide‐angle X‐ray scattering (GIWAXS) characterization of the polymer film morphology/microstructure reveals that an over‐abundance of EGn sidechains generates large polymer crystallites, which can suppress ion exchange. Lastly, time‐of‐flight secondary ion mass spectrometry (ToF‐SIMS) indicates sidechain/electrolyte identity does not influence the electrolyte penetration depth into the films, and EGn sidechain inclusion increases electrolyte cation uptake. The material structural design insight and guidelines regarding the polymer‐electrolyte ion insertion/expulsion dynamics reported here should be of significant utility for developing next‐generation mixed ionic‐electronic conducting materials.

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Low band-gap diketopyrrolopyrrole-containing polymers for near infrared electrochromic and photovoltaic applications

Cited by 30 publications

References 59 publications

Electrochromic Behavior of Donor-Acceptor Polymers Containing Diketopyrrolopyrrole Unit

Electrochromic Behavior of Donor-Acceptor Polymers Containing Diketopyrrolopyrrole Unit

Visible and near-infrared electrochromic thiophene–diketopyrrolopyrrole polymers

Enhanced Optical Contrast and Switching in Near‐Infrared Electrochromic Devices by Optimizing Conjugated Polymer Oligo(Ethylene Glycol) Sidechain Content and Gel Electrolyte Composition

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