Donor-acceptor-donor molecules based on diketopyrrolopyrrole, benzodipyrrolidone and naphthodipyrrolidone: Organic crystal field-effect transistors

Deng, Zhifeng; Hao, Xiaoli; Zhang, Pengfei; Li, Leiquan; Yuan, Xiaoguang; Ai, Tinghua; Bao, Weiwei; Kou, Kaichang

doi:10.1016/j.dyepig.2018.11.028

Cited by 24 publications

(5 citation statements)

References 29 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%

“…Therefore, the extension of π‐conjugation at the perpendicular direction of the polymer main chain in P‐NDF lead to a negative impact on the enhancement of both intramolecular coplanarity and intermolecular packing compared to the P‐BDF polymer, thus significantly differing from the many cases as reported in the literature in which the π‐conjugation extension of the (macro)molecular backbone (typically along the main chains) usually results in the materials with stronger and closer π–π stackings. [ 28,39 ]…”

Section: Resultsmentioning

confidence: 99%

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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%

Section: Resultsmentioning

confidence: 99%

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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“…It is well known that the high crystallinity is favorable for the charge carrier mobility, thereby improving the charge transport, as expected in the case of an IDT‐based polymer. [ 44 ]…”

Section: Resultsmentioning

confidence: 99%

From Transistors to Phototransistors by Tailoring the Polymer Stacking

Cui

Liang

Liu

et al. 2022

Adv Elect Materials

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of transistors, thus exhibiting higher photo sensitivity and lower noise levels than conventional photodiodes and photo conductors. [5][6][7][8][9][10] Although inorganic photo transistors (e.g., single crystalline silicon and InAlAs-InGaAs) have attracted considerable attention from both the industry and the global market, the high-temperature processing under vacuum, the poor compatibility with flexible substrates, and the limited sensing areas significantly restrict their further developments and practical applications. [11,12] Therefore, realizing low-cost, high-sensitivity, and highly flexible phototransistors in a large-scale area has quickly become an important research focus.Conjugated polymers (CPs) are wellknown and promising candidates for solution-processable and cost-effective semiconductor materials due to several attractive merits, including intrinsic flexibility, incorporation of functionality via molecular design, and ease of achieving large-scale and low-cost device fabrication through facile methods, such as spin coating, drop-casting, and inkjet printing. [13][14][15][16][17] In recent years, although the rational tuning of the electronic energy levels and band gaps is widely investigated, the charge carrier mobility of the reported CPs is still much lower than that of amorphous silicon (≈1 cm 2 V −1 s −1 ). Extensive studies have demonstrated that the wide absorption band of CPs determines the efficient photoinduced charge carrier generation under illumination, while the high charge carrier mobility ensures the swift charge transport and collection at the electrodes. [18][19][20] However, the strong π-π packing and high exciton binding energy (0.3-1 eV) desirable when aiming for high mobility of the CPs are generally detrimental for their use as the photoactive layer in the phototransistors. [21][22] Thus, how to balance the π-π packing and charge carrier mobility of the CPs is of crucial significance for fabricating high-performance phototransistors.Recent reports have demonstrated that diketopyrrolopyrrole (DPP)-based CPs are considered as highly prospective photoactive materials for solution-processed organic optoelectronic devices like organic solar cells (OSCs) and organic FETs (OFETs). [23][24][25][26][27] By selectively amalgamating the electrondeficient DPP units with proper electron-rich units, the D-A copolymers could show good planarity, controllable conjugated It is universally acknowledged that highly photosensitive transistors are strongly dependent on the high carrier mobility of polymer-based semiconductors. However, the polymer π-π stacking and aggregation, required to increase the charge mobility, conversely inhibit the dissociation of photogenerated charge carriers, in turn accelerating the geminate recombination of electron-hole pairs. To explore the effects of charge mobility and polymer stacking on the photoresponsivity of the phototransistors, here, two alternating copolymers are synthesized, namely P-PPAB-IDT and P-PPAB-BDT, by palladium-catalyzed Stille coupling of PP...

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“…However, BDP was stable at both conditions. Soon thereafter, Z. Deng et al used bithiophene to substitute both side of the NDP [47]. Using obtained molecule to construct OFETs showed n-type behavior with a μ e up to 0.26 cm 2 V −1 s −1 .…”

Section: Small Molecules and Monomersmentioning

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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Donor-acceptor-donor molecules based on diketopyrrolopyrrole, benzodipyrrolidone and naphthodipyrrolidone: Organic crystal field-effect transistors

Cited by 24 publications

References 29 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

From Transistors to Phototransistors by Tailoring the Polymer Stacking

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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