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Keywords = 5,6-difluorobenzotriazole

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12 pages, 2708 KiB  
Article
Synthesis of π-Conjugated Polymers Containing Benzotriazole Units via Palladium-Catalyzed Direct C-H Cross-Coupling Polycondensation for OLEDs Applications
by Dong Han, Jingwen Li, Qiang Zhang, Zewang He, Zhiwei Wu, Jingting Chu and Yan Lu
Polymers 2021, 13(2), 254; https://doi.org/10.3390/polym13020254 - 14 Jan 2021
Cited by 13 | Viewed by 3748
Abstract
Four D-π-A conjugated polymers, namely P1–P4, which contain benzotriazole building blocks in their backbone as acceptor, are synthesized via palladium-catalyzed direct C-H cross-coupling polycondensation of 5,6-difluorobenzotriazole with different thiophene derivatives, including 3-octylthiophene, 2,2’-bithiophene, thieno[3,4-b][1,4]dioxine, and 4,4-dioctyl-4H-silolo-[3,2-b:4,5-b’]dithiophene as donor units, respectively. Taking the polymer [...] Read more.
Four D-π-A conjugated polymers, namely P1–P4, which contain benzotriazole building blocks in their backbone as acceptor, are synthesized via palladium-catalyzed direct C-H cross-coupling polycondensation of 5,6-difluorobenzotriazole with different thiophene derivatives, including 3-octylthiophene, 2,2’-bithiophene, thieno[3,4-b][1,4]dioxine, and 4,4-dioctyl-4H-silolo-[3,2-b:4,5-b’]dithiophene as donor units, respectively. Taking the polymer P1 as an example, the chemical structure of the polymer is demonstrated by 1H and 19F NMR spectra. The optical, electrochemical, and thermal properties of these polymers are assessed by UV–vis absorption and fluorescence spectroscopy, cyclic voltammetry (CV), and thermal gravimetric analysis (TGA), respectively. DFT simulations of all polymers are also performed to understand their physicochemical properties. Furthermore, P1 and P2, which have relatively higher molecular weights and better fluorescent quantum efficiency than those of P3 and P4, are utilized as lighting emitters for organic light-emitting diodes (OLEDs), affording promising green and red luminescence with 0.07% and 0.14% of maximum external quantum efficiency, respectively, based on a device with an architecture of ITO/PEDOT:PSS/PTAA/the polymer emitting layer/TPBi/LiF/Al. Full article
(This article belongs to the Special Issue Synthetic Approaches and Applications of Conjugated Polymers)
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11 pages, 4355 KiB  
Article
Aggregation Controlled Charge Generation in Fullerene Based Bulk Heterojunction Polymer Solar Cells: Effect of Additive
by Washat Ware, Tia Wright, Yimin Mao, Shubo Han, Jessa Guffie, Evgeny O. Danilov, Jeromy Rech, Wei You, Zhiping Luo and Bhoj Gautam
Polymers 2021, 13(1), 115; https://doi.org/10.3390/polym13010115 - 30 Dec 2020
Cited by 8 | Viewed by 3330
Abstract
Optimization of charge generation in polymer blends is crucial for the fabrication of highly efficient polymer solar cells. While the impacts of the polymer chemical structure, energy alignment, and interface on charge generation have been well studied, not much is known about the [...] Read more.
Optimization of charge generation in polymer blends is crucial for the fabrication of highly efficient polymer solar cells. While the impacts of the polymer chemical structure, energy alignment, and interface on charge generation have been well studied, not much is known about the impact of polymer aggregation on charge generation. Here, we studied the impact of aggregation on charge generation using transient absorption spectroscopy, neutron scattering, and atomic force microscopy. Our measurements indicate that the 1,8-diiodooctane additive can change the aggregation behavior of poly(benzodithiophene-alt-dithienyl difluorobenzotriazole (PBnDT-FTAZ) and phenyl-C61-butyric acid methyl ester (PCBM)polymer blends and impact the charge generation process. Our observations show that the charge generation can be optimized by tuning the aggregation in polymer blends, which can be beneficial for the design of highly efficient fullerene-based organic photovoltaic devices. Full article
(This article belongs to the Special Issue Structure-Property Relationships in Organic Semiconductors)
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16 pages, 16703 KiB  
Article
Donor-Acceptor-Type Copolymers Based on 3,4-Propylenedioxy-thiophene and 5,6-Difluorobenzotriazole: Synthesis and Electrochromic Properties
by Fanda Feng, Lingqian Kong, Hongmei Du, Jinsheng Zhao and Junhong Zhang
Polymers 2018, 10(4), 427; https://doi.org/10.3390/polym10040427 - 11 Apr 2018
Cited by 15 | Viewed by 4758
Abstract
Three solution-processable D-A-type conjugated polymers P1, P2 and P3 were successfully synthesized via the Pd-catalyzed Stille cross-coupling copolymerization approach, with 6,8-Dibromo-3,3-bis-decyl-3,4-dihydro-2H-thieno[3,4-b][1,4] dioxepine (M1) and 2,5-Bis(trimethylstannanyl)thiophene (M3) as the donor units and 4,7-Dibromo-5,6-difluoro-2-(2-hexyl-decyl)-2H-benzotriazole (M2) as the acceptor [...] Read more.
Three solution-processable D-A-type conjugated polymers P1, P2 and P3 were successfully synthesized via the Pd-catalyzed Stille cross-coupling copolymerization approach, with 6,8-Dibromo-3,3-bis-decyl-3,4-dihydro-2H-thieno[3,4-b][1,4] dioxepine (M1) and 2,5-Bis(trimethylstannanyl)thiophene (M3) as the donor units and 4,7-Dibromo-5,6-difluoro-2-(2-hexyl-decyl)-2H-benzotriazole (M2) as the acceptor unit, wherein the feed ratio of the three units was 1:3:4 (M1:M2:M3, the same below), 1:1:2 and 3:1:4 for P1, P2, and P3, respectively. The results obtained by our test showed that the feed ratio between the D and A units had a significant effect on both the electrochemical and the spectroelectrochemical properties of the three polymers. The copolymers exhibited a gradually deepening red color in neutral state with the increase of M1 content and then turned to a transmissive grey color in the oxidation state. Also, three copolymers showed good performance in electrochromic parameters, which mainly consists of optical contrast, response time, and coloration efficiency. In general, the excellent electrochromic performances of the copolymers make them outstanding candidates for electrochromic material applications. Full article
(This article belongs to the Special Issue π-Stacked Polymers)
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