Butterfly Effects Arising from Starting Materials in Fused-Ring Electron Acceptors

Li, Tengfei; Wu, Yao; Zhou, Jiadong; Li, Mengyang; Wu, Jiada; Hu, Qin; Jia, Boyu; Pan, Xiran; Zhang, Maojie; Tang, Zheng; Xie, Zengqi; Russell, Thomas P.; Zhan, Xiaowei

doi:10.1021/jacs.0c09800

Cited by 93 publications

(73 citation statements)

References 59 publications

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“…Then, we calculated the charge transfer state energy (E ct ) from the electroluminescence (EL) and highly sensitive external quantum efficiency (sEQE) spectra (as shown in Figure S8, Supporting Information), using the method described in the literature. [45][46][47] As listed in Table 3, the E ct values increase gradually from 1.34 eV for 2Th-2F-based device to 1.36 and 1.38 eV for BTh-Th-2F and 2BTh-2F-based ones.…”

Section: Photovoltaic Propertiesmentioning

confidence: 84%

Simple Nonfused Ring Electron Acceptors with 3D Network Packing Structure Boosting the Efficiency of Organic Solar Cells to 15.44%

Wang

Lü

Liu

et al. 2021

Advanced Energy Materials

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125

121

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Zhan et al. reported a fused ring electron acceptor (FREA) ITIC with an acceptordonor-acceptor (A-D-A) type structure. [1] Subsequently, numerous FREAs are developed by researchers, which largely promoted the photovoltaic performance of OSCs. Recently, Zou et al. developed a series of A-DA′D-A type FREAs (Y6 series). Up to now, the highest power conversion efficiency (PCE) of OSCs based on FREAs has reached 18%, demonstrating the bright future for practical application. [2][3][4][5][6][7][8][9] Although FREAs can achieve high efficiency, they are expensive and their syntheses are complicated, which usually includes low-yield ring-closure reactions. For the commercialization of OSCs, it is highly desired to develop highperformance and low-cost nonfullerene acceptors. Therefore, we want to develop simple nonfused ring electron acceptors (NFREAs) to replace the high-cost FREAs. In 2017, we first postulated and proved that intramolecular noncovalent interactions could be used to partially replace chemical bonds to synthesize NFREAs. [10] Since then, small fused ring building blocks such as indacenodithiophene (IDT), [11][12][13][14] cyclopentadithiophene (CPDT), [15][16][17][18][19][20][21][22][23][24] etc., were often used for the construction of NFREAs. Later, researchers also developed fully nonfused ring electron acceptors. [25][26][27] However, the photovoltaic performance of the solar cells based on NFREAs is still far behind the FREAs.Typical FREAs consist of a fused ring core, side chains, and two electron-withdrawing terminal groups. [28][29][30][31] The planar fused ring core is beneficial for the electron delocalization. The side chain can increase the solubility and affect the molecular stacking of acceptors. The electron-withdrawing terminal group such as 3-(1,1-dicyanomethylene)-5,6-difluoro-1-indanone can induce a strong intramolecular charge transfer (ICT) effect in the acceptor molecule, which can remarkably broaden the absorption, lower the energy levels (especially the lowest unoccupied molecular orbital (LUMO)), and enhance the molecular stacking. [32][33][34] Besides these basic characteristics, recent reports begin to focus on molecular stacking model. There is growing evidence that high-performance FREAs possess a 3D network packing structure, being in favor of facilitating multiple charge transport, achieving small exciton binding energy, and reducing energy loss in OSCs. [5,[35][36][37][38][39] Unlike rigid FREAs, the molecular Three nonfused ring electron acceptors (NFREAs; 2Th-2F, BTh-Th-2F, and 2BTh-2F) with thieno[3,2-b]thiophene bearing two bis(4-butylphenyl)amino substituents as the core, 3-octylthiophene or 3-octylthieno[3,2-b]thiophene as the spacer, and 3-(1,1-dicyanomethylene)-5,6-difluoro-1-indanone as the terminal group are designed and synthesized. The molar extinction coefficient of acceptors and the electron mobility of blend films gradually increase with increasing π-conjugation length. Moreover, 2BTh-2F displays a planar molecular conformation assisted by S•••N and S•••O intr...

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Section: Photovoltaic Propertiesmentioning

confidence: 84%

Simple Nonfused Ring Electron Acceptors with 3D Network Packing Structure Boosting the Efficiency of Organic Solar Cells to 15.44%

Wang

Lü

Liu

et al. 2021

Advanced Energy Materials

Self Cite

125

121

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“…As these fused-ring building blocks, all contain a few sulfur-and/or nitrogen-heteroaromatic five-membered rings and thus are electron-rich 4 , 8 , 17 , a strong intramolecular charge transfer (ICT) effect can be formed when they conjugately link with the electron-deficient end-capping groups, which endows the flexibilities in modulating absorption spectra and molecular energy levels of the NFAs 24 – 27 . On the other hand, the bulky alkyls on the fused-ring building blocks not only guarantee good solubilities of the NFAs 25 , 27 , 28 but also ensure the intermolecular π−π stacking of the NFAs to mainly occur at the end-capping groups, because such a molecular packing mode is crucial for their electron-accepting capability 19 , 20 , 29 – 31 . Putting all of the above characteristics together, it is a big challenge to replace the fused-ring building blocks with the non-fused units.…”

Section: Introductionmentioning

confidence: 99%

Completely non-fused electron acceptor with 3D-interpenetrated crystalline structure enables efficient and stable organic solar cell

et al. 2021

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Non-fullerene acceptors (NFAs) based on non-fused conjugated structures have more potential to realize low-cost organic photovoltaic (OPV) cells. However, their power conversion efficiencies (PCEs) are much lower than those of the fused-ring NFAs. Herein, a new bithiophene-based non-fused core (TT-Pi) featuring good planarity as well as large steric hindrance was designed, based on which a completely non-fused NFA, A4T-16, was developed. The single-crystal result of A4T-16 reveals that a three-dimensional interpenetrating network can be formed due to the compact π–π stacking between the adjacent end-capping groups. A high PCE of 15.2% is achieved based on PBDB-TF:A4T-16, which is the highest value for the cells based on the non-fused NFAs. Notably, the device retains ~84% of its initial PCE after 1300 h under the simulated AM 1.5 G illumination (100 mW cm−2). Overall, this work provides insight into molecule design of the non-fused NFAs from the aspect of molecular geometry control.

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“…Generally, A‐D‐A‐type acceptors are extended conjugation length to enhance absorption to NIR region, which contribute to forming complementary absorption with donors. [ 311–316 ] However, this strategy accompanied by tedious, high‐cost synthesis and a complicated purification process, which undoubtedly hinder their mass production. In consideration of this problem, He et al.…”

Section: Polycyclic Furan Materials Used In Oscsmentioning

confidence: 99%

Recent Advances of Furan and Its Derivatives Based Semiconductor Materials for Organic Photovoltaics

Zheng

Huo

2021

Small Methods

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The state‐of‐the‐art bulk‐heterojunction (BHJ)‐type organic solar cells (OSCs) have exhibited power conversion efficiencies (PCEs) of exceeding 18%. Thereinto, thiophene and its fused‐ring derivatives play significant roles in facilitating the development of OSCs due to their excellent semiconducting natures. Furan as thiophene analogue, is a ubiquitous motif in naturally occurring organic compounds. Driven by the advantages of furan, such as less steric hindrance, good solubility, excellent stacking, strong rigidity and fluorescence, biomass derived fractions, more and more research groups focus on the furan‐based materials for using in OSCs in the past decade. To systematically understand the developments of furan‐based photovoltaic materials, the relationships between the molecular structures, optoelectronic properties, and photovoltaic performances for the furan‐based semiconductor materials including single furan, benzofuran, benzodifuran (BDF) (containing thienobenzofuran (TBF)), naphthodifurans (NDF), and polycyclic furan are summarized. Finally, the empirical regularities and perspectives of the development of this kind of new organic semiconductor materials are extracted.

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Butterfly Effects Arising from Starting Materials in Fused-Ring Electron Acceptors

Cited by 93 publications

References 59 publications

Simple Nonfused Ring Electron Acceptors with 3D Network Packing Structure Boosting the Efficiency of Organic Solar Cells to 15.44%

Simple Nonfused Ring Electron Acceptors with 3D Network Packing Structure Boosting the Efficiency of Organic Solar Cells to 15.44%

Completely non-fused electron acceptor with 3D-interpenetrated crystalline structure enables efficient and stable organic solar cell

Recent Advances of Furan and Its Derivatives Based Semiconductor Materials for Organic Photovoltaics

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