Synthesis and photovoltaic properties of donor–acceptor conjugated polymers based on 4,7-dithienyl-2,1,3-benzothiadiazole functionalized silole

Wang, Xunchang; Su, Qiang; Li, Yuda; Cheng, Chang; Tong, Junfeng; He, Luying; Li, Hui; Shu, Ge; Wang, Feng

doi:10.1016/j.synthmet.2016.07.016

Cited by 15 publications

(8 citation statements)

References 35 publications

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“…39,40 P1 (M n = 13 000) had the highest molecular weight of the three polymers, while P2 (M n = 8000) and P3 (M n = 10 000) molecular weights were lower. The much lower M w for P2 containing the DFBSe moiety could be a result of the Se atom inhibition of the polymerization as reported by Kuramochi et al 38 Structural defects by the potential homocoupling and/or branched chain side reactions of the thiophene derivatives can be observed in polymers by 1 H NMR. 49 Since DFBT and DFBSe do not contain protons after polymerization, except as an end-group that can be very difficult to identify, 1 H NMR spectra (Figure S1) were inspected for extra peaks in the aromatic region for thiophene, which would signify homocoupling and/or branch chain side reactions between the 2,5-dithienylsilole units.…”

Section: ■ Results and Discussionmentioning

confidence: 74%

“…6−8 Furthermore, silole-containing polymers with the dithienosilole moiety have been used to fabricate OFETs with carrier mobilities as high as ∼0.02−0.08 cm 2 /(V s). 9,10 On the other hand, OFETs fabricated from silolecontaining polymers with the 2,5-dithienylsilole moiety result in lower carrier mobilities on the order of 10 −4 −10 −6 cm 2 /(V s) 1,11 due to the lack of planarity of the phenyl substituents at the 3-and 5-positions. Our group has been interested in the 2,5-dithienylsilole as functional building block for conducting polymers due to the ability to add a variety of functionalities at the 3,5-positions of the silole.…”

Section: ■ Introductionmentioning

confidence: 99%

“…28,29 C−H activation has been shown to be useful for the crosscoupling of electron-poor building blocks such as 1,2,4,5tetrafluorobenzene, 30 perylene diimides, 31 thieno[3,4-c]pyrrole-4,6-dione, 32 and 3,6-dithiophen-2-yl-2,5-dihydro-1,4diketopyrrolo[3,4-c]-pyrroles. 33 Likewise, Marder and co-workers recently reported the synthesis of a thienyl derivative of 5,6dicyano[2,1,3]benzothiadiazole (DCBT) by direct arylation reaction and showed that it is a comparably strong acceptor to benzo[1,2-c:4,5-c]bis [1,2,5]thiadiazole. 4 Consequently, we believe that DArP could provide a useful and efficient way to incorporate electron-poor compounds into high performance π-conjugated polymeric materials.…”

Section: ■ Introductionmentioning

confidence: 99%

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Direct Arylation Polycondensation of 2,5-Dithienylsilole with a Series of Difluorobenzodiimine-Based Electron Acceptors

et al. 2017

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This paper describes the use of direct arylation polymerization (DArP) reaction to synthesize three new 2,5-dithienylsilole polymers with a series of difluorobenzodiimine-based electron acceptors: 5,6-difluoro[2,1,3]benzothiadiazole (DFBT), 5,6-difluoro[2,1,3]benzoselenadiazole (DFBSe), and 5,6-difluoro[2,1,3]benzotriazole (DFBTA). The Stille cross-coupling polycondensation reaction was performed to confirm the structural quality of the polymers; however, only low molecular weight oligomers were obtained. This result demonstrates the power of the DArP method to prepare polymers containing strong electron-deficient monomers. During our investigation, it was found that Fagnou’s condition did not produce polymers, whereas the condition reported by Ozawa and co-workers gave polymers with moderate molecular weights. This is the first known example of the synthesis of 2,5-dithienylsilole-containing polymers by the DArP. Our polymers have reduced band gaps (<2.0 eV), and P1 provided hole mobility values in the range of 10–2 cm2/(V s), which is superior to previously reported values for 2,5-dithienylsilole-containing polymers (10–4–10–6 cm2/(V s)) and comparable to dithienosilole-containing polymers.

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Section: ■ Results and Discussionmentioning

confidence: 74%

Section: ■ Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Direct Arylation Polycondensation of 2,5-Dithienylsilole with a Series of Difluorobenzodiimine-Based Electron Acceptors

et al. 2017

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“…The most successful polymeric dopant and its corresponding solution processable CP are PSS and PEDOT:PSS, respectively. Since PEDOT:PSS was invented by Bayer AG company in 1994, it has been widely applied as conductive film in organic optoelectronic devices, electrochemical energy conversion and storage devices, biosensors, thermoelectric devices, etc . The conductivities of the most widely used Clevios P VP AI 4083 and PH1000 are between 10 −3 ‐10 −4 and 0.2‐1 S⋅cm −1 , respectively.…”

Section: Introductionmentioning

confidence: 99%

Synergetic Effect of Perfluorooctanoic Acid on the Preparation of Poly(3,4‐ethylenedioxythiophene): Lignosulfonate Aqueous Dispersions with High Film Conductivity

Wang

et al. 2019

ChemistrySelect

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Developing poly(3,4‐ethylenedioxythiophene) (PEDOT) conducting polymers (CPs) aqueous dispersions with high film conductivity is an attractive task in scientific and industrial communities. Herein, we proposed to apply small molecular perfluorooctanoic acid (PFA) as assistant dopant to cooperate with major polymeric dopant of lignosulfonate (LGS) to prepare PEDOT aqueous dispersions together. Through optimizing the usage amount of PFA, a high film conductivity of 0.1255 S⋅cm−1 was obtained. In contrast, the film conductivity of the CP prepared without PFA was only 0.0228 S⋅cm−1. By lucubrating the structure of CPs, we found that PFA is capable of promoting the polymerization, doping and aggregation of PEDOT in the preparation process of PEDOT:LGS CP and the conductivity enhancement can be attributed to the enhancement of molecular weight, doping degree and aggregation of PEDOT. Moreover, the other physical‐chemical properties of PEDOT:LGS CPs including transmittance, work function and waterproofness were not obviously affected by PFA. This facile strategy based on physical mixing of small molecular and polymeric dopants may opens up a new window for the preparation of high performance CPs aqueous dispersions.

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“…Benzodithiophene (BDT) is one of the most widely used structural units for donor polymers in PSCs because of its rigid and large planar structure [ 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 ]. Recently, side chains of BDT-containing conjugated polymers have been found to play a critical role in affecting polymer packing and bulk heterojunction (BHJ) morphology.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Photovoltaic Properties of 2D-Conjugated Polymers Based on Alkylthiothienyl-Substituted Benzodithiophene and Different Accepting Units

Wang

Cheng

et al. 2018

Polymers

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Abstract:Two new low bandgap conjugated polymers, PBDTS-ID and PBDTS-DTNT, containing isoindigo (ID) and naphtho [1,2-c:5,6-c ]bis[1,2,5]thiadiazole (NT), respectively, as an electron-deficient unit and alkylthiothienyl-substituted benzodithiophene (BDTS) as an electron-rich unit, were designed and synthesized by palladium-catalyzed Stille polycondensation. Both polymers showed good thermal stability up to 330 • C and broad absorption ranging from 300 to 842 nm. Electrochemical measurement revealed that PBDTS-ID and PBDTS-DTNT exhibited relatively low-lying highest occupied molecular orbital energy levels at −5.40 and −5.24 eV, respectively. These features might be beneficial for obtaining reasonable high open-circuit voltage and high short-circuit current. Polymer solar cells (PSCs) were fabricated with an inverted structure of indium-tin oxide/poly(ethylenimine ethoxylate)/polymer:PC 71 BM/MoO 3 /Ag. As a preliminary result, the PSCs based on PBDTS-ID and PBDTS-DTNT exhibited moderate power conversion efficiencies of 2.70% and 2.71%, respectively.

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Synthesis and photovoltaic properties of donor–acceptor conjugated polymers based on 4,7-dithienyl-2,1,3-benzothiadiazole functionalized silole

Cited by 15 publications

References 35 publications

Direct Arylation Polycondensation of 2,5-Dithienylsilole with a Series of Difluorobenzodiimine-Based Electron Acceptors

Direct Arylation Polycondensation of 2,5-Dithienylsilole with a Series of Difluorobenzodiimine-Based Electron Acceptors

Synergetic Effect of Perfluorooctanoic Acid on the Preparation of Poly(3,4‐ethylenedioxythiophene): Lignosulfonate Aqueous Dispersions with High Film Conductivity

Synthesis and Photovoltaic Properties of 2D-Conjugated Polymers Based on Alkylthiothienyl-Substituted Benzodithiophene and Different Accepting Units

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