Cyclopenta[c]thiophene- and Diketopyrrolopyrrole-Based Red-Green-Blue Electrochromic Polymers

Debnath, Sashi; Masilamani, Ganesh; Agrawal, Abhijeet R.; Kumar, Neha Rani; Kumar, Chandan; Zade, Sanjio S.; Bedi, Anjan

doi:10.1055/s-0042-1757979

Cited by 5 publications

(5 citation statements)

References 38 publications

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“…Spectroelectrochemical performance was tested by stepping up the voltage [ 43 ], and the color changes of the three polymer films from the neutral state to the oxidation state were recorded, as shown in Figure 6 . For PBPE-1, when the voltage was 0 V, the polymer had a distinct absorption peak at 492 nm due to the π-π* electronic transition [ 44 ].…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Characterization of Solution-Processible Donor-Acceptor Electrochromic Conjugated Copolymers Based on Quinoxalino[2′,3′:9,10]phenanthro[4,5-abc]phenazine as the Acceptor Unit

Wang

Kong

et al. 2023

Polymers

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Donor-acceptor (D-A) type conjugated polymers are of high interest in the field of electrochromism. In this study, three novel conjugated copolymers (PBPE–1, PBPE-2 and PBPE-3) based on quinoxalino[2′,3′:9,10]phenanthro[4,5-abc]phenazine (A) as the acceptor unit and 4,8-bis((2-octyldodecyl)oxy)benzo[1,2-b:4,5-b′]dithiophene (D1) and 3,3-didecyl-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine (ProDOT-decyl2, D2) as the donor units with different donor-to-acceptor ratios were successfully synthesized through Stille coupling polymerization. The polymers were then characterized by cyclic voltammetry (CV), fourier transform infrared (FT-IR) spectoscopy, X-ray photoelectron spectroscopy (XPS), spectroelectrochemistry, thermogravimetry (TG), electrochromic switching and colorimetry. Optical band gap values were calculated as 1.99 eV, 2.02 eV and 2.03 eV, respectively. The three copolymers have good solubility, distinct redox peaks, wide absorption spectra, good thermal stabilities, bright color changes and significant electrochromic switching properties. Compared to the other two copolymers, the PBPE-3 film exhibited high coloration efficiency values of 513 cm2·C−1 at 504 nm and 475 cm2·C−1 at 1500 nm. The films have the advantage of exhibiting cathodic and anodic coloration.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Characterization of Solution-Processible Donor-Acceptor Electrochromic Conjugated Copolymers Based on Quinoxalino[2′,3′:9,10]phenanthro[4,5-abc]phenazine as the Acceptor Unit

Wang

Kong

et al. 2023

Polymers

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“…Figure 4 e shows the charge distribution of the material, and it can be seen that there is a negative charge around the carbonyl group. All the above tests are based on the b3lyp-D3/def2tzvp unit of Gauss 16 [ 42 , 43 , 44 , 45 , 46 ]. Figure S5 shows the results of simulated UV with maximum absorption peaks at 434 nm and 639 nm, respectively.…”

Section: Resultsmentioning

confidence: 99%

Preparation of Dye Semiconductors via Coupling Polymerization Catalyzed by Two Catalysts and Application to Transistor

Ren,

Zhang,

Wang

et al. 2023

Molecules

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Organic dye semiconductors have received increasing attention as the next generation of semiconductors, and one of their potential applications is as a core component of organic transistors. In this study, two novel diketopyrrolopyrrole (DPP) dye core-based materials were designed and separately prepared using Stille coupling reactions under different palladium catalyst conditions. The molecular weights and elemental compositions were tested to demonstrate that both catalysts could be used to successfully prepare materials of this structure, with the main differences being the weight-average molecular weight and the dispersion index. PDPP-2Py-2Tz I with a longer conjugation length exhibited better thermodynamic stability than the counterpart polymer PDPP-2Py-2Tz II. The intrinsic optical properties of the polymers were relatively similar, while the electrochemical tests showed small differences in their energy levels. The polymers obtained with different catalysts displayed similar and moderate electron mobility in transistor devices, while PDPP-2Py-2Tz I possessed a higher switching ratio. Our study provides a comparison of such dye materials under different catalytic conditions and also demonstrates the great potential of dye materials for optoelectronic applications.

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“…In this context, Zade et al extensively synthesized CPS-and CPSe-based building blocks, polymers, and copolymers [29,31]. CPS and CPSe are among the building blocks, when polymerized or copolymerized, that produce materials showing a decent-to-excellent charge transport [37,38], electrochromic switching, or which complete the red-green-blue color wheel [39]. While most CPS-based polymers were found to be amorphous, copolymers based on CPS and bithiazole building blocks showed superior p-type hole mobility arising from the semicrystalline nature of the polymers [37].…”

Section: Introductionmentioning

confidence: 99%

Origin of Optoelectronic Contradictions in 3,4-Cycloalkyl[c]-chalcogenophenes: A Computational Study

Masilamani,

Krishna,

Debnath

et al. 2023

Polymers

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The planar morphology of the backbone significantly contributes to the subtle optoelectronic features of π-conjugated polymers. On the other hand, the atomistic tuning of an otherwise identical π-backbone could also impact optoelectronic properties systematically. In this manuscript, we compare a series of 3,4-cycloalkylchalcogenophenes by tuning them atomistically using group-16 elements. Additionally, the effect of systematically extending these building blocks in the form of oligomers and polymers is studied. The size of the 3,4-substitution affected the morphology of the oligomers. In addition, the heteroatoms contributed to a further alteration in their geometry and resultant optoelectronic properties. The chalcogenophenes, containing smaller 3,4-cycloalkanes, resulted in lower bandgap oligomers or polymers compared to those with larger 3,4-cycloalkanes. Natural bonding orbital (NBO) calculations were performed to understand the disparity alongside the contour maps of frontier molecular orbitals (FMO).

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Cyclopenta[c]thiophene- and Diketopyrrolopyrrole-Based Red-Green-Blue Electrochromic Polymers

Cited by 5 publications

References 38 publications

Synthesis and Characterization of Solution-Processible Donor-Acceptor Electrochromic Conjugated Copolymers Based on Quinoxalino[2′,3′:9,10]phenanthro[4,5-abc]phenazine as the Acceptor Unit

Synthesis and Characterization of Solution-Processible Donor-Acceptor Electrochromic Conjugated Copolymers Based on Quinoxalino[2′,3′:9,10]phenanthro[4,5-abc]phenazine as the Acceptor Unit

Preparation of Dye Semiconductors via Coupling Polymerization Catalyzed by Two Catalysts and Application to Transistor

Origin of Optoelectronic Contradictions in 3,4-Cycloalkyl[c]-chalcogenophenes: A Computational Study

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