Generating a three-dimensional non-fullerene electron acceptor by combining inexpensive spiro[fluorene-9,9′-xanthene] and cyanopyridone functionalities

Kadam, Gajanan; Anuradha, .; Agarwal, Anubha; Puyad, Avinash L.; La, Duong Duc; Evans, Richard A.; Li, Jingliang; Gupta, Akhil; Bhosale, Sheshanath V.

doi:10.1039/c8qm00067k

Cited by 22 publications

(7 citation statements)

References 45 publications

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“…Poly(3-hexylthiophene) (P3HT) is one of the most widely used and cheapest commercially available donors. Gupta and co-workers designed naphthalene diimide (NDI) core-based A-A′-A-type, − V-shaped A–D–A-type, and H-shaped SMAs to be compatible with P3HT, , accomplishing the PCE from 4.76 to 7.65%. Peng and co-workers developed a star-shaped SMA and improved the PCE of P3HT-based PSCs to 8.25% .…”

Section: Resultsmentioning

confidence: 99%

Regulating the Packing of Non-Fullerene Acceptors via Multiple Noncovalent Interactions for Enhancing the Performance of Organic Solar Cells

Feng

Tang

et al. 2020

ACS Appl. Mater. Interfaces

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Three noncovalently fused-ring electron acceptors (FOC6-IC, FOC6-FIC, and FOC2C6-2FIC) are synthesized. Single crystals of FOC6-IC and FOC2C6-2FIC are prepared, and structure analyses reveal that the molecular backbone can be planarized via the formation of the intramolecular noncovalent interactions. These acceptor molecules can be packed closely in the solid state via π–π stacking and static interactions between the central phenylene unit and the terminal group with a distance of 3.3–3.4 Å. Besides, multiple intermolecular noncovalent interactions can be observed in the single crystal structure of the fluorinated acceptor FOC2C6-2FIC, which help increase the crystallinity of acceptors and the charge mobility of the blends. Photovoltaic devices based on FOC2C6-2FIC give a power conversion efficiency of 12.36%, higher than 12.08% for FOC6-FIC and 10.80% for FOC6-IC.

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Section: Resultsmentioning

confidence: 99%

Regulating the Packing of Non-Fullerene Acceptors via Multiple Noncovalent Interactions for Enhancing the Performance of Organic Solar Cells

Feng

Tang

et al. 2020

ACS Appl. Mater. Interfaces

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“…Star‐shaped A– π –D– π –A NFAs consist of a central donor core linked to several linear chains arranged in a 3D geometry. [ 26–28 ] In contrast to their linear analogs, star‐shaped NFAs ensure 1) tunability of the lower unoccupied orbital levels (LUMO) through modification of the acceptor units, with a direct effect on the open‐circuit voltage (

V_{OC}

) of the corresponding OPVs; 2) possible broadening of the absorption spectrum (and thus improved solar absorption) up to the near‐infrared region; and 3) minimization of the molecular aggregation and enhancement of the exciton dissociation due to the 3D structures that may lead to high short‐circuit current density (

J_{SC}

) in OPVs. [ 29–31 ] For a high‐performance star‐shaped NFA, choosing the central core and the attached arms is crucial.…”

Section: Introductionmentioning

confidence: 99%

Flexible Organic Photovoltaics with Star‐Shaped Nonfullerene Acceptors End Capped with Indene Malononitrile and Barbiturate Derivatives

et al. 2022

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The design and synthesis of three star‐shaped nonfullerene (NFA) acceptors, TPA‐2T‐INCN, TPA‐2T‐BAB, and TPA‐T‐INCN, based on a triphenylamine (TPA) core and linked through π‐conjugated thiophene (T) spacers to different terminal units (3‐oxo‐2,3‐dihydro‐1H‐inden‐1‐ylidene) malononitrile, INCN, and 1,3‐dimethylbarbituric acid, BAB), are reported. These materials are blended with the widely used poly(3‐hexylthiophene‐2,5‐diyl) (P3HT) donor polymer and tested in flexible organic photovoltaics (OPVs). The NFAs capped with the strong electron‐withdrawing INCN unit perform best in OPVs. Both P3HT:TPA‐T‐INCN and P3HT:TPA‐2T‐INCN blends also show the highest photoluminescence quenching efficiency (95.8% and 92.6%, respectively). Surprisingly, when reducing the number of T spacers from 2 to 1, the solubility of the NFAs in o‐dichlorobenzene increases, leading to easier processing during the OPV fabrication and better surface morphology. This explains the best performance of TPA‐T‐INCN‐based blends in OPVs, with a champion power conversion efficiency of 1.13%.

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“…By using the “same-A-strategy” (SAS), BTA3 can match well with several BTA-based polymers and realize an ultra-high V OC of 1.15–1.24 V. − Most importantly, BTA3 can match with P3HT and achieve a high PCE of 5.64% with a V OC of 0.90 V, which indicates that A 2 –A 1 –D–A 1 –A 2 type NFAs have a large potential to improve the photovoltaic performance of P3HT and the chemical structures need to be further modified. As we all know, introducing heteroatoms (O, N, and S) into a fused aromatic ring can increase solar light absorption and enhance charge mobilities and intermolecular/intramolecular interactions, contributing to high photovoltaic performance. − For example, the Huang group , reported a highly planar molecular acceptor, (IDT)-4CN, containing multiple noncovalent conformational locks because of the O and N atoms to improve the photovoltaic performance.…”

Section: Introductionmentioning

confidence: 99%

Effects of Oxygen Atoms Introduced at Different Positions of Non-Fullerene Acceptors in the Performance of Organic Solar Cells with Poly(3-hexylthiophene)

Xiao

Wang

et al. 2019

ACS Appl. Mater. Interfaces

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With the development of large-area fabrication technologies for organic solar cells (OSCs), poly(3-hexylthiophene) (P3HT) is the best choice as a photovoltaic donor polymer because it can be easily synthesized in the scale of kilograms at low cost. However, non-fullerene acceptors (NFAs) matching with P3HT for high performance OSCs are very rare. Herein, by introducing oxygen atoms into the side chains or the fused-ring core of indaceno[1,2-b:5,6-b′]dithiophene, we synthesized two new A 2 −A 1 −D−A 1 −A 2 type NFAs, where benzotriazole (BTA) and 2-(1,1dicyanomethylene)rhodanine were used as the bridged A 1 and terminal A 2 , respectively. The final NFAs, named BTA43 and BTA53, show wider absorption spectra and enhanced intermolecular/intramolecular interaction in comparison with their analogue BTA3 without oxygen atoms. The photovoltaic devices based on P3HT:BTA43 and P3HT:BTA53 can achieve a high power conversion efficiency of 6.56 and 6.31%, respectively, which are obviously higher than that of BTA3 (5.64%). Our results provide a simple and effective strategy to design promising NFAs to pair with the classic photovoltaic polymer P3HT.

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Generating a three-dimensional non-fullerene electron acceptor by combining inexpensive spiro[fluorene-9,9′-xanthene] and cyanopyridone functionalities

Abstract: A spiro[fluorene-9,9′-xanthene]-functionalized non-fullerene acceptor A1 [D : A1 = 1 : 1.2; P3HT(D) = 5.84%, PTB7(D) = 7.21%].

Cited by 22 publications

References 45 publications

Regulating the Packing of Non-Fullerene Acceptors via Multiple Noncovalent Interactions for Enhancing the Performance of Organic Solar Cells

Regulating the Packing of Non-Fullerene Acceptors via Multiple Noncovalent Interactions for Enhancing the Performance of Organic Solar Cells

Flexible Organic Photovoltaics with Star‐Shaped Nonfullerene Acceptors End Capped with Indene Malononitrile and Barbiturate Derivatives

Effects of Oxygen Atoms Introduced at Different Positions of Non-Fullerene Acceptors in the Performance of Organic Solar Cells with Poly(3-hexylthiophene)

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