1,6-Naphthodipyrrolidone-based donor–acceptor polymers with low bandgap

Zhang, Haichang; Ying, Shian; Tieke, Bernd; Zhang, Jun; Yang, Wenjun

doi:10.1016/j.polymer.2015.01.035

Cited by 15 publications

(6 citation statements)

References 26 publications

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“…The remarkably large bathochromic shifts of the polymers (over 150 nm for both P‐BDF and P‐NDF) should be ascribed the fact that during polymerization, the formation of a large extension of π‐conjugation system as well as the strong D–A interactions within the polymer backbones which can cause strong ICT process to generate a more delocalized intramolecular π‐orbitals and thus increase the efficient conjugation lengths. [ 39,40 ] Again, the P‐BDF polymer showed a larger redshift of maximum optical absorption in the solution when compared to P‐NDF, similar as the trend between the absorption of the two monomers, which further confirmed coplanarity could affect more on the optical absorption than the perpendicular π‐extended counterparts. For the polymer films, as shown in Figure 4b,c, a redshifted absorption was also observed for both polymers when compared to their solution states.…”

Section: Resultsmentioning

confidence: 61%

Benzo/Naphthodifuranone‐Based Polymers: Effect of Perpendicular‐Extended Main Chain π‐Conjugation on Organic Field‐Effect Transistor Performances

Dai

Zheng

et al. 2021

Macromol. Rapid Commun.

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For polymer semiconductors, the backbone structure plays an essential role in determining their physicochemical properties and charge transport behaviors. In this work, two donor–acceptor‐type polymers (P‐BDF and P‐NDF) based on benzodifuranone (BDF) and naphthodifunarone (NDF) as electron‐deficient moieties and indaceno‐dithiophene as electron‐rich groups are designed, synthesized and, for the first time, applied in organic field‐effect transistor. P‐BDF and P‐NDF differ from their backbone structures while P‐BDF has a more planar backbone conformation due to its smaller conjugated core size and P‐NDF features a perpendicular‐extended main chain structure. As a result, P‐BDF polymer exhibits bathochromic optical absorption, deeper molecular orbital energy levels, and more importantly, closer π‐stacking and stronger aggregation in the solid state and thus affords a more promising hole mobility of up to 0.85 cm2 V−1 s−1 in OFET devices, while that of the P‐NDF‐based devices is only 0.55 cm2 V−1 s−1. The results suggest the great potential of BDF/NDF‐type chromophores in constructing novel organic semiconductors and also indicate that the main chain coplanarity of polymer semiconductors is more essential than the sole extension of π‐conjugations (especially at the perpendicular direction of polymer main chains) for the design of high‐performance OFET materials.

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Section: Resultsmentioning

confidence: 61%

Benzo/Naphthodifuranone‐Based Polymers: Effect of Perpendicular‐Extended Main Chain π‐Conjugation on Organic Field‐Effect Transistor Performances

Dai

Zheng

et al. 2021

Macromol. Rapid Commun.

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“…The same group also synthesized dihalogenated, t -Boc-protected benzodipyrrolidone 31.5 and naphthodipyrrolidone 31.12 by condensation and electrophilic aromatic substitution (Scheme ). ,, Suzuki coupling with fluorene 30.1 gives the soluble precursor polymers 31.6 and 31.13 with latent hydrogen-bonding. Heating to 200 °C releases isobutene and renders the polymers 31.7 and 31.14 insoluble.…”

Section: Thermal Cleavagementioning

confidence: 99%

Immobilization Strategies for Organic Semiconducting Conjugated Polymers

et al. 2018

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This Review details synthetic routes toward and properties of insoluble polymeric organic semiconductors obtained through desolubilization strategies. Typical applications include fixation of donor-acceptor bulk-heterojunction morphologies in organic photovoltaic cells, cross-linking of charge transport materials and active emitters in light emitting diodes or similar devices, and immobilization of morphologies in field effect transistors. A second important application is the structuring of organic semiconductors, using them as photoresists. After desolubilization, removal of the nonirradiated resist leads to elevated, micron-sized features of the semiconductor. In this Review, different strategies for desolubilization are covered. By photochemical or thermal cleavage of solubility-mediating groups such as esters, sulfonium salts, amides, ethers, and acetals or by retro-Diels-Alder reactions, volatile elimination products and the insoluble semiconductor are formed. In another case, desolubilization is achieved by cross-linking via functional groups present in the polymer side chains including vinyl, halide, silicone, boronic acid, and azide functionalities, which polymerize thermally or photochemically. Alternatively, small molecular additives such as photoacids, oligothiols, or oligoazides result in network formation in combination with compatible functional groups present in the immobilizable polymers. Advantages and disadvantages of the respective methods are discussed.

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“…Naphthodipyrrolidone is a novel chromophore firstly developed by Zhang and Tieke [20,46]. The chemical structure of this chromophore is analogy to isoDPP and BDP (Figure 1), except the core of the NDP is tetracyclic.…”

Section: Small Molecules and Monomersmentioning

confidence: 99%

“…Later, the same group reported another four D–A copolymers constructed by NDP as acceptor, and fluorine (P42, P43) or benzo[1,2-b:4,5-]dithiophene (BDT, P46, P47) as donor units [46]. All the polymers exhibited broad optical absorption between 400 nm and 1000 nm, and a narrow band gap (1.30 to 1.60 eV).…”

Section: Polymersmentioning

confidence: 99%

Conjugated Polymers Containing Building Blocks 1,3,4,6-Tetraarylpyrrolo[3,2-b]pyrrole-2,5-dione (isoDPP), Benzodipyrrolidone (BDP) or Naphthodipyrrolidone (NDP): A Review

Deng

et al. 2019

Polymers

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π-Conjugated organic donor–acceptor (D–A) type polymers are widely developed and used in electronic device. Among which, diketopyrrolopyrrole (DPP)-based polymers have received the most attention due to their high performances. The novel chromophores named 1,3,4,6-tetraarylpyrrolo[3,2-b]pyrrole-2,5-dione (isoDPP), benzodipyrrolidone (BDP) and naphthodipyrrolidone (NDP) are resemble DPP in chemical structure. IsoDPP is an isomer of DPP, with the switching position of carbonyl and amide units. The cores of BDP and NDP are tri- and tetracyclic, whereas isoDPP is bicyclic. π-Conjugation extension could result polymers with distinct optical, electrochemical and device performance. It is expected that the polymers containing these high-performance electron-deficient pigments are potential in the electronic device applications, and have the potential to be better than the DPP-based ones. IsoDPP, BDP, and NDP based polymers are synthesized since 2011, and have not receive desirable attention. In this work, the synthesis, properties (optical and electrochemical characteristics), electronic device as well as their relationship depending on core-extension or structure subtle optimization have been reviewed. The final goal is to outline a theoretical scaffold for the design the D–A type conjugated polymers, which is potential for high-performance electronic devices.

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1,6-Naphthodipyrrolidone-based donor–acceptor polymers with low bandgap

Cited by 15 publications

References 26 publications

Benzo/Naphthodifuranone‐Based Polymers: Effect of Perpendicular‐Extended Main Chain π‐Conjugation on Organic Field‐Effect Transistor Performances

Benzo/Naphthodifuranone‐Based Polymers: Effect of Perpendicular‐Extended Main Chain π‐Conjugation on Organic Field‐Effect Transistor Performances

Immobilization Strategies for Organic Semiconducting Conjugated Polymers

Conjugated Polymers Containing Building Blocks 1,3,4,6-Tetraarylpyrrolo[3,2-b]pyrrole-2,5-dione (isoDPP), Benzodipyrrolidone (BDP) or Naphthodipyrrolidone (NDP): A Review

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