3D network acceptor with gradient hydrogen bond interaction as a bifunctional layer in quasiplanar heterojunction organic solar cells

Chen, Hui; Lai, Hanjian; Jiang, Qiuju; Lai, Xue; Zhu, Yulin; Qu, Jianfei; Wu, Qinghe; He, Feng

doi:10.1016/j.nanoen.2023.108593

Cited by 7 publications

(5 citation statements)

References 44 publications

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“…For example, He and co-workers developed two SMAs (BTIC-OH-δ and BTIC-OH-β) with a hydroxy-functionalized end group. 60 Crystallographic analysis confirmed the presence of strong intermolecular hydrogen bonding interactions in BTIC-OH-δ, while such interactions are notably absent in BTIC-OH-β, which endows BTIC-OH-δ with tighter π−π stacking and higher electron mobility. As a consequence, the BTIC-OH-δ-based device exhibited enhanced device efficiency and stability compared with that of the BTIC-OH-β-based device.…”

Section: Asymmetric End-group Substitutionmentioning

confidence: 83%

“…This can be achieved through halogen (fluorine or chlorine) and hydroxyl cosubstituted end groups, which provide the necessary hydrogen bonding sites between two different end groups. For example, He and co-workers developed two SMAs (BTIC-OH-δ and BTIC-OH-β) with a hydroxy-functionalized end group . Crystallographic analysis confirmed the presence of strong intermolecular hydrogen bonding interactions in BTIC-OH-δ, while such interactions are notably absent in BTIC-OH-β, which endows BTIC-OH-δ with tighter π–π stacking and higher electron mobility.…”

Section: Summary and Perspectivesmentioning

confidence: 99%

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End-Group Engineering of Nonfullerene Acceptors for High-Efficiency Organic Solar Cells

Luo,

Yan,

Yang

2023

Acc. Mater. Res.

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Conspectus In recent years, organic solar cells (OSCs) have made significant advancements due to a deeper understanding of molecular design and device technology. One area of molecular design that has contributed to these advancements is the emergence of nonfullerene small-molecule acceptors (SMAs) and polymerized SMAs. The molecular design strategy of state-of-the-art SMAs focuses on two aspects: the electron-rich central core unit and electron-deficient end groups. Different from the manipulation of the central cores, end-group engineering is a direct and efficient means to adjust the physicochemical properties and crystallization/aggregation behavior of acceptors, leading to enhanced photovoltaic performance. On the basis of our recent research advances, herein we focus on the topic of end-group engineering of nonfullerene acceptors, aiming to provide a comprehensive understanding of the optimization of end groups for the design of high-performance acceptor materials. In this Account, first, we systematically compare the difference between thiophene-fused and benzene-fused end groups in synthetic routes and molecular energy levels. Unlike the centrosymmetric benzene, the axisymmetric thiophene-fused end groups have two different fusion modes, resulting in their different frontier orbital energy levels. Second, we offer a wrought review of SMAs with thiophene-fused or thiophene derivatives-fused end groups, emphasizing the important role of thiophene derivatives-fused end groups in enhancing molecular packing, improving exciton bonding energy, and reducing energy loss in OSCs. Additionally, we reveal the specific reason why the thiophene-fused end group with an α/β fusion site and the thiophene-fused end group with a β/γ fusion site have significantly different molecular energy levels. Third, we summarize the photovoltaic parameters and conventional physicochemical properties of polymerized SMAs based on monobromobenzene-fused end groups and fluorobromine (or chlorobromide) cosubstituted benzene-fused end groups. We demonstrate that regioregular polymerized SMAs show great prospects in realizing high-performance all-polymer solar cells by eliminating the disorder of molecular backbone structure with pure monobromobenzene-fused end groups. Furthermore, the halogenation strategy (fluorination and chlorination) is also an effective method for designing high-performance PSMAs with large electron mobility induced by the intermolecular noncovalent interactions of halogen···H, halogen···S, and halogen···halogen. Finally, we analyze the role of asymmetric end group substitution for developing high-performance SMAs. In comparison with symmetric SMAs, the asymmetric one achieves low energy loss while ensuring sufficient charge separation. As a summary and perspective, we discuss the current questions regarding end groups and propose our insights into the future development of nonfullerene acceptors with novel end groups toward low-cost and high-performance OSCs.

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Section: Asymmetric End-group Substitutionmentioning

confidence: 83%

Section: Summary and Perspectivesmentioning

confidence: 99%

End-Group Engineering of Nonfullerene Acceptors for High-Efficiency Organic Solar Cells

Luo,

Yan,

Yang

2023

Acc. Mater. Res.

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“…Similarly, He et al. employed the same strategy to demonstrate that hydrogen‐assisted molecular stacking is conducive to enhancing the efficiency and stability of the device [8b] . In addition, our recent work revealed that the formation of hydrogen bonds in BTP‐PhC6‐C11 leads to improved molecular stacking and enhanced electronic coupling, resulting in higher fill factor (FF) and device efficiency compared to Y6 [5c] .…”

Section: Introductionmentioning

confidence: 80%

Precise Methylation Yields Acceptor with Hydrogen‐Bonding Network for High‐Efficiency and Thermally Stable Polymer Solar Cells

Wei,

Zhang,

Chen

et al. 2024

Angewandte Chemie

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Utilizing intermolecular hydrogen‐bonding interactions stands for an effective approach in advancing the efficiency and stability of small‐molecule acceptors (SMAs) for polymer solar cells. Herein, we synthesized three SMAs (Qo1, Qo2, and Qo3) using indeno[1,2‐b]quinoxalin‐11‐one (Qox) as the electron‐deficient group, with the incorporation of a methylation strategy. Through crystallographic analysis, it is observed that two Qox‐based methylated acceptors (Qo2 and Qo3) exhibit multiple hydrogen bond‐assisted 3D network transport structures, in contrast to the 2D transport structure observed in gem‐dichlorinated counterpart (Qo4). Notably, Qo2 exhibits multiple and stronger hydrogen‐bonding interactions compared with Qo3. Consequently, PM6 : Qo2 device realizes the highest power conversion efficiency (PCE) of 18.4 %, surpassing the efficiencies of devices based on Qo1 (15.8 %), Qo3 (16.7 %), and Qo4 (2.4 %). This remarkable PCE in PM6 : Qo2 device can be primarily ascribed to the enhanced donor‐acceptor miscibility, more favorable medium structure, and more efficient charge transfer and collection behavior. Moreover, the PM6 : Qo2 device demonstrates exceptional thermal stability, retaining 82.8 % of its initial PCE after undergoing annealing at 65 °C for 250 hours. Our research showcases that precise methylation, particularly targeting the formation of intermolecular hydrogen‐bonding interactions to tune crystal packing patterns, represents a promising strategy in the molecular design of efficient and stable SMAs.

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“…That is, most PHJ devices need to use orthogonal solvents between the two layers to prevent the corrosion of the underlying film during sequential film formation. 11,12 In recent years, researchers have conducted extensive methods to address this issue. For example, Lee et al 13 introduced a novel method called the spontaneously spreading (SS) process for processing the active layer, which is suitable for large-scale fabrication under ambient conditions.…”

mentioning

confidence: 99%

“…That is, most PHJ devices need to use orthogonal solvents between the two layers to prevent the corrosion of the underlying film during sequential film formation. 11,12…”

mentioning

confidence: 99%

Spontaneously spreading film process to improve the photovoltaic performance of organic solar cells with PHJ structure

Cheng,

Wang,

Pei

et al. 2023

Chem. Commun.

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3D network acceptor with gradient hydrogen bond interaction as a bifunctional layer in quasiplanar heterojunction organic solar cells

Cited by 7 publications

References 44 publications

End-Group Engineering of Nonfullerene Acceptors for High-Efficiency Organic Solar Cells

End-Group Engineering of Nonfullerene Acceptors for High-Efficiency Organic Solar Cells

Precise Methylation Yields Acceptor with Hydrogen‐Bonding Network for High‐Efficiency and Thermally Stable Polymer Solar Cells

Spontaneously spreading film process to improve the photovoltaic performance of organic solar cells with PHJ structure

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