Regioregular and Random Difluorobenzothiadiazole Electron Donor–Acceptor Polymer Semiconductors for Thin-Film Transistors and Polymer Solar Cells

Deng, Ping; Wu, Bo; Lei, Yanlian; Cao, Huanyang; Ong, Beng S.

doi:10.1021/acs.macromol.5b02754

Cited by 32 publications

(31 citation statements)

References 51 publications

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“…The polymer exhibits typical dual band absorption. The lower energy band in the range of 300–500 nm can be attributed to the internal charge transfer transition and the higher energy band at the range of 500–900 nm is originated from the π–π * transition . The optical band gap of the polymer film is calculated to be 1.44 eV using thin films' absorption onsets.…”

Section: Resultsmentioning

confidence: 99%

An Asymmetric Furan/Thieno[3,2‐b]Thiophene Diketopyrrolopyrrole Building Block for Annealing‐Free Green‐Solvent Processable Organic Thin‐Film Transistors

Ding

et al. 2018

Macromol. Rapid Commun.

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A new asymmetric furan and thieno[3,2-b]thiophene flanked diketopyrrolopyrrole (TTFDPP) building block for conjugated polymers is designed and used to generate a donor-acceptor semiconducting polymer, poly[3-(furan-2-yl)-2,5-bis(2-octyldodecyl)-6-(thieno[3,2-b]thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione-alt-thieno[3,2-b]thiophene] (abbreviated to PTTFDPP-TT), consisting of TTFDPP unit copolymerized with thieno[3,2-b]thiophene comonomer (TT), which is further synthesized. Results demonstrate that PTTFDPP-TT-based thin-film transistors in a bottom-gate bottom-contact device configuration exhibit typical hole-transporting property, with weak temperature dependence for charge carrier mobility from room temperature to 200 °C. In addition, the good solubility of PTTFDPP-TT due to the incorporation of a polar furan unit and an asymmetric conjugated structure makes it able to be solution processed with a less toxic nonchlorinated solvent such as toluene, demonstrating comparable performance with that prepared from chlorinated solution. These results suggest PTTFDPP-TT as a promising organic semiconductor candidate for annealing-free, environmentally benign, and less energy-consuming applications in large-area flexible organic electronic devices.

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Section: Resultsmentioning

confidence: 99%

An Asymmetric Furan/Thieno[3,2‐b]Thiophene Diketopyrrolopyrrole Building Block for Annealing‐Free Green‐Solvent Processable Organic Thin‐Film Transistors

Ding

et al. 2018

Macromol. Rapid Commun.

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“…In fact, recent results clearly indicate that regioregular terpolymers display higher charge mobilities and better photovoltaic performance than the respective random terpolymers. [61][62][63][64] Alternatively, conjugated D-A polymers with more than three types of donor and acceptor moieties can be prepared by coupling more than three monomers in the same way as for terpolymers. The proper combination of electron donors and acceptors in these conjugated polymers will enable us not only to finely modulate the electronic structures of the backbones but also to tune interchain interactions and packing as well as thin-film morphology.…”

Section: Discussionmentioning

confidence: 99%

Conjugated D–A terpolymers for organic field-effect transistors and solar cells

Luo

Liu

Zhang

2017

Polym J

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The incorporation of additional electron donors or acceptors into the backbones of conjugated polymers with alternating donors and acceptors results in various conjugated D-A terpolymers. The presence of additional electron donors or acceptors in the conjugated backbones can modulate the electronic absorptions and highest occupied molecular orbital/lowest unoccupied molecular orbital levels, as well as interchain interactions and thin-film morphology. Because of these structural features, conjugated D-A terpolymers have been intensively investigated in recent years for applications in field-effect transistors and photovoltaic cells. In this review, we introduce the recent developments of conjugated D-A terpolymers with various combinations of electron donors and acceptors, and discuss the future perspectives for conjugated terpolymers. In recent decades, conjugated polymers have demonstrated promising applications in flexible, large-area and low-cost electronic devices, such as organic field-effect transistors (OFETs) 1-3 and solar cells (OSCs). [4][5][6][7] This is attributed to the conjugated electronic and polymeric structures of these polymers, resulting in semiconducting properties with good solution processability, mechanical property and thermal stability. 8,9 Among the conjugated polymers, conjugated alternating polymers consisting of both electron donors (D) and electron acceptors (A), referred to as conjugated D-A polymers, [10][11][12][13][14][15][16][17] have been extensively investigated in recent years. The studies indicate that electronic absorptions, highest occupied molecular orbital/lowest unoccupied molecular orbital (HOMO/LUMO) energies (and bandgaps), interchain interactions and thin-film morphologies of conjugated D-A polymers can be effectively tuned 10-17 by properly varying the electron donors and acceptors as well as the linkers. Consequently, the semiconducting performance of conjugated D-A polymers can be tuned in this way. In fact, polymeric p-type, n-type and even ambipolar semiconductors with high charge mobilities have been developed on the basis of conjugated D-A polymers. 18-21 Moreover, conjugated D-A polymers have been successfully utilized as either electron donors or acceptors for OSCs with high power conversion efficiencies (PCEs). [22][23][24][25] Apart from conjugated polymers with alternating electron donor and acceptor moieties, conjugated D-A terpolymers, which contain either one kind of acceptor/two types of electron donors (2D1A) or one kind of donor/two types of electron acceptors (1D2A) in the backbones as illustrated in Scheme 1, have received increased attention. It is expected that an additional dimension is generated for tuning the electronic structures of conjugated polymers and thus their absorptions and HOMO/LUMO levels as well as interchain packing 8,26 with such conjugated D-A terpolymers. Moreover, the combination of existing electron donors and acceptors can yield a huge number of terpolymers, which can be prepared in the same manner as conventional D-A ...

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“…This phenomenon indicates that the complex had an ability to cause direct double-strand scission. 32 Due to the disruption of DNA into small pieces, EB staining could not be observed in the presence of 2a at concentrations higher than 50 µ M. At 10 µ M the nuclease activity of 1a, 1b, 1d, 2b, and 2e was the most effective. Interestingly, any further increase in the concentration of these molecules resulted in suppression of DNA-cleaving ability.…”

Section: Hydrolytic Cleavage Activitymentioning

confidence: 95%

Synthesis, in vitro DNA interactions, cytotoxicities, antioxidative activities, and topoisomerase inhibition potentials of Mn(II), Co(II), Ni(II), Cu(II), and Zn(II) complexes with azo-oxime ligands

Ayvaz¹,

Turan²,

Dural³

et al. 2017

Turk J Chem

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Mn(II), Co(II), Ni(II), Cu(II), and Zn(II) transition metal complexes of 2-hydroxy-5-[(E)-(4-phenyl) diazenyl]benzaldehyde oxime and 2-hydroxy-5-[(E)-(4-nitrophenyl) diazenyl] benzaldehyde oxime ligands were synthesized and characterized through NMR, IR, ESI mass, and UV analysis. DNA binding abilities of the complexes were revealed using a UV-Vis spectrophotometer with the absorption titration and competitive binding techniques. Hydrolytic and oxidative DNA cleavage activities under different conditions were also proved. Topoisomerase I inhibition efficiencies and in vitro free radical scavenging activities of all complexes were examined. Finally, the selective cytotoxic potentials of all complexes were evaluated in human colon cancer, normal colon, and fibroblast cell lines using the water-soluble tetrazolium salt (WST-1) assay. The complexes had the ability to intercalate into stacked base pairs of DNA and topoisomerase I activity was reasonably inhibited in their presence in 0.4 mM concentrations. The abilities for scavenging of DPPH and hydroxyl radicals were found to be higher than those of known standard antioxidants (ascorbic acid, butylated hydroxyanisole, and mannitol). The results obtained from the cytotoxicity experiments are especially promising for further research, which must be carried out for the evaluation of the studied complexes as anticancer drugs.

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Regioregular and Random Difluorobenzothiadiazole Electron Donor–Acceptor Polymer Semiconductors for Thin-Film Transistors and Polymer Solar Cells

Cited by 32 publications

References 51 publications

An Asymmetric Furan/Thieno[3,2‐b]Thiophene Diketopyrrolopyrrole Building Block for Annealing‐Free Green‐Solvent Processable Organic Thin‐Film Transistors

An Asymmetric Furan/Thieno[3,2‐b]Thiophene Diketopyrrolopyrrole Building Block for Annealing‐Free Green‐Solvent Processable Organic Thin‐Film Transistors

Conjugated D–A terpolymers for organic field-effect transistors and solar cells

Synthesis, in vitro DNA interactions, cytotoxicities, antioxidative activities, and topoisomerase inhibition potentials of Mn(II), Co(II), Ni(II), Cu(II), and Zn(II) complexes with azo-oxime ligands

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