Novel 4,8-benzobisthiazole copolymers and their field-effect transistor and photovoltaic applications

Conboy, Gary; Taylor, Rupert G. D.; Findlay, Neil J.; Kanibolotsky, Alexander L.; Inigo, Anto R.; Ghosh, Sanjay S.; Ebenhoch, Bernd; Jagadamma, Lethy Krishnan; Thalluri, Gopala Krishna V. V.; Sajjad, Muhammad T.; Samuel, Ifor D. W.; Skabara, Peter J.

doi:10.1039/c7tc03959j

Cited by 30 publications

(16 citation statements)

References 54 publications

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“…In this work, we choose benzobis(thiazole) (BBTz) and cyclopentadithiophene (CPDT) as molecular core and donor units, respectively, to check the above molecular design strategy. The BBTz unit was chosen for the design of nonfullerene acceptors, despite rarely utilized in photovoltaic materials, due to the following considerations: 1) S···N noncovalent interaction can be formed between the nitrogen atom of the BBTz unit and the sulfur atom of the CPDT unit to lock the molecular geometry, 2) the quinoid‐resonance effect of the BBTz unit can be utilized to narrow the bandgap of the nonfullerene acceptors, 3) the electron‐withdrawing property of BBTz unit can help lower the HOMO level. The D‐C‐D molecular structure is flanked by two different electron‐withdrawing terminals, (2‐(5,6‐difluoro‐3‐oxo‐2,3‐dihydro‐1 H ‐inden‐1‐ylidene)malononitrile and 2‐(6‐oxo‐5,6‐dihydro‐4 H ‐cyclopenta[ c ]thiophen‐4‐ylidene)malononitrile), to check the effect of terminals on the device performance, thus resulting in two novel nonfullerene acceptors (X‐PCIC and X1‐PCIC) with similar properties in the absorption range and energy levels, but a significant difference in terminal packing strength.…”

Section: Introductionmentioning

confidence: 99%

Near‐Infrared Nonfullerene Acceptors Based on Benzobis(thiazole) Unit for Efficient Organic Solar Cells with Low Energy Loss

Zhan

Lau

et al. 2019

Small Methods

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The simultaneous achievement of a low energy loss and high external quantum efficiency (EQE) response is the prerequisite for high power conversion efficiencies of organic solar cells (OSCs). Herein, this issue is examined through the design of two novel near‐infrared (NIR) nonfullerene acceptors (X‐PCIC and X1‐PCIC) with an absorption extending to 900 nm, which is realized by using benzobis(thiazole) unit as the core. This study reveals that benzobis(thiazole) unit with the quinoid‐resonance effect and electron‐withdrawing property is a good building block in extending absorption and maintaining suitable energy levels. Single crystal cultivation proves the function of S···N noncovalent interaction in locking molecular geometry. Besides, through adopting two different terminals (fluorinated terminal for X‐PCIC and thiophene‐fused terminal for X1‐PCIC), it is found that an increase in the J‐aggregation strength has a significant positive effect on the EQE response of the devices through the formation of more suitable domain sizes and crystallinity in the films, while the energy loss remains low (≈0.53 eV) and unaffected. Thus, a high efficiency of 11.50% is presented for OSC based on the X‐PCIC with stronger J‐aggregation strength, better than that (10.17%) based on the X1‐PCIC with weaker J‐aggregation strength. This work clearly demonstrates the application of benzobis(thiazole) unit in efficient small molecule acceptors and the importance of J‐aggregation modulation for the simultaneous achievement of low energy loss and high EQE response.

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Section: Introductionmentioning

confidence: 99%

Near‐Infrared Nonfullerene Acceptors Based on Benzobis(thiazole) Unit for Efficient Organic Solar Cells with Low Energy Loss

Zhan

Lau

et al. 2019

Small Methods

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“…19 The intermediate compound 3 was prepared by using lithium diisopropylamide (LDA) and pinacol borate according to the literature. [12][13][14][15][16][17][18] Finally, the key intermediates 2a-2c were respectively coupled with compound 3 using the Suzuki coupling method with the catalyst Pd(PPh 3 ) 4 to prepare the three target conjugated compounds DPP-BVCNT, DPP-2FBVCNT, and DPP-3FBVCNT. The synthetic routes of the target conjugated compounds and intermediates are shown in Scheme 1.…”

Section: Synthesis and Thermal Propertiesmentioning

confidence: 99%

“…1 H NMR, 13 C NMR, and 19 F NMR spectra of synthetic intermediates and target small molecules were tested and recorded on a Bruker Avance III 400 HD NMR spectrometer or were characterized by using a Bruker Avance III 500WB NMR spectrometer. The reported 13 C NMR spectra were not 19F decoupled and hence were reported as empiric enumeration of the observed signals.…”

Section: Measurements and Characterization Of Compoundsmentioning

confidence: 99%

“…Intermediate compounds 2a-2c and 3 were prepared according to the reported methods. [12][13][14][15][16][17][18][19] General Preparation Method of the Key BVCNT-Based Intermediates (2a-2c)…”

Section: Synthetic Proceduresmentioning

confidence: 99%

“…1 H NMR (400 MHz, CDCl 3 , TMS): δ ¼ 7.65-7.60 (m, 2H), 7.51-7.48 (m, 1H), 7.42-7.41 (m, 1H), 7.36-7.34 (m, 1H), 7.26 (s, 1H), 7.10-7.07 (m, 1H). 13…”

Section: Synthetic Proceduresmentioning

confidence: 99%

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Synthesis and Performance of (E)-3-Phenyl-2-(thiophen-2-yl)acrylonitrile-Based Small-Molecule Semiconductors

Wang

et al. 2019

Organic Materials

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Based on diketopyrrolopyrrole (DPP) and (E)-3-phenyl-2-(thiophen-2-yl)acrylonitrile (BVCNT)-linked conjugated backbones, three donor–acceptor type conjugated organic small-molecule compounds DPP-BVCNT, DPP-2FBVCNT, and DPP-3FBVCNT were designed and synthesized. Among them, the 2-decyltetradecyl side chain on the DPP acceptor unit was used to ensure the solubility of the material. The fluorine (F) atoms combined with the nitrile on the BVCNT donor unit were used to adjust electronic structures and charge carrier transport properties of the conjugated system. All the three small molecules exhibited good solution dispersibility and thermal stability, providing an important guarantee for the solution processing and annealing optimization of organic field-effect transistors (OFETs). The top-gate-bottom-contact OFET devices based on these compounds showed good ambipolar or p-type performances. The relationship between molecular structures and OFET performances indicated that the F-substitution and its position significantly affected their charge carrier transport properties. The F-substitution could remarkably change the performance from p-type to ambipolar especially for the outer-side-F-substituted compound DPP-2FBVCNT, which showed the best OFET performances with the maximum hole/electron mobilities of 0.023/0.220 cm2 V−1 s−1. These results provided a promising idea for developing small-molecule OFET materials with good solution processability, good thermal stability, and high ambipolar performances.

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Molecular Regioisomerism of Benzobisthiazole‐Based Conjugated Polymers Promotes Photocatalytic Hydrogen Production

Hu,

Ding,

Feng

et al. 2024

Adv Funct Materials

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Polymer semiconductors hold great promise for photocatalytic hydrogen production due to their diverse structures and functions. Nevertheless, their photocatalytic performances are usually compromised by rapid charge recombination. Herein, a molecular regioisomerism strategy of benzobisthiazole (BT)‐based conjugated polymers is proposed for manipulating their optoelectronic properties through varying the conjugation directions of BT units. Despite subtle structural differences, the 4,8‐subsituted sample LCP‐BT‐48 exhibits an remarkably improved charge separation capability and a sixfold increase in the photocatalytic hydrogen production rate in comparison with those of the 2,6‐subsituted counterpart. Theoretical analysis demonstrates that the superior optoelectronic property of LCP‐BT‐48 is attributed to its sp2 carbon‐conjugated skeletons and enhanced local polarization electric field between BT and neighboring π‐units. This work provides a new paradigm for regulating charge‐transfer dynamics in conjugated polymers for efficient photocatalysis.

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Novel 4,8-benzobisthiazole copolymers and their field-effect transistor and photovoltaic applications

Abstract: A series of BBT-containing copolymers featuring the 4,8-conjugation pathway is presented and evaluated.

Cited by 30 publications

References 54 publications

Near‐Infrared Nonfullerene Acceptors Based on Benzobis(thiazole) Unit for Efficient Organic Solar Cells with Low Energy Loss

Near‐Infrared Nonfullerene Acceptors Based on Benzobis(thiazole) Unit for Efficient Organic Solar Cells with Low Energy Loss

Synthesis and Performance of (E)-3-Phenyl-2-(thiophen-2-yl)acrylonitrile-Based Small-Molecule Semiconductors

Molecular Regioisomerism of Benzobisthiazole‐Based Conjugated Polymers Promotes Photocatalytic Hydrogen Production

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