Linear and propeller-like fluoro-isoindigo based donor–acceptor small molecules for organic solar cells

Ouhib, Farid; Tomassetti, Mirco; Dierckx, Wouter; Verstappen, Pieter; Wislez, Arnaud; Duwez, Anne‐Sophie; Lemaur, Vincent; Lazzaroni, Roberto; Manca, Jean; Maes, Wouter; Jérôme, Christine; Detrembleur, Christophe

doi:10.1016/j.orgel.2015.01.033

Cited by 16 publications

(9 citation statements)

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“…Our observations highlight the crucial role played by molecular structure/architecture and thin film morphology in the performance of organic solar cells and field-effect transistors, 42,58 Exchange of the central benzothiadiazole acceptor by an isoindigo moiety resulted in deeper HOMO-LUMO energy levels, enabling higher open-circuit voltages to be reached in bulk heterojunction organic solar cells.…”

Section: Discussionmentioning

confidence: 77%

“…squaraine, 17 benzotriazole, 18 alkyl cyanoacetate, 19 diketopyrrolopyrrole, 20 benzothiadiazole, 21 and isoindigo 22 ), most often combined with electron-donating oligothiophenes or arylamine units, have been developed over the years. [37][38][39][40][41][42][43] Further clarification of the molecular architecture -(device) property relationships is required, though, to fully exploit the synthetic versatility toward top-efficiency devices. Among the electron-poor components, isoindigo (IID) is a promising molecular building block for solar celland transistor applications because of its straightforward large-scale synthesis, strong light absorption, photochemical stability and stacking tendency.…”

Section: Introductionmentioning

confidence: 99%

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Branched and linear A₂–D–A₁–D–A₂isoindigo-based solution-processable small molecules for organic field-effect transistors and solar cells

et al. 2015

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To establish a correlation between the molecular structure, physicochemical properties, thin film morphology, charge carrier mobility and photovoltaic performance of isoindigo-based electron donor type molecular semiconductors, a series of branched and linear A 2 -D-A 1 -D-A 2 small molecules (A = acceptor, D = donor)are synthesized. The extended π-conjugated molecular chromophores have an electron-accepting isoindigo core, a bridging oligothiophene electron donor part and terminal octyl cyanoacrylate acceptor moieties. Their photophysical, thermal and electrochemical properties are analysed and the materials are applied in organic field-effect transistors and bulk heterojunction organic solar cells. Compared to an analogous benzothiadiazole-based small molecule, the isoindigo core deepens the HOMO energy level, enabling higher open-circuit voltages in organic solar cell. The linear isoindigo-based small molecule shows an enhanced hole mobility compared to the branched derivatives. The best power conversion efficiency of the investigated set is also obtained for the solar cell based on the linear (CA-3T-IID-3T-CA) donor molecule in combination with PC 71 BM.A 2 -D-A 1 -D-A 2 type small molecules were synthesized, providing a solar cell efficiency of 1.9% and hole mobility of 3.7 x 10 -3 cm 2 V -1 s -1 .

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Section: Discussionmentioning

confidence: 77%

Section: Introductionmentioning

confidence: 99%

Branched and linear A₂–D–A₁–D–A₂isoindigo-based solution-processable small molecules for organic field-effect transistors and solar cells

et al. 2015

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“…To establish a correlation between molecular structure and various properties such as PCE, Detrembleur et al studied a series of isoindigo-based small molecules by manipulating the side chain (linear vs branched) 18 and the overall architecture (linear vs propeller-like). 19 Despite an improvement to charge transport, the PCE remained below 2%, nonetheless, the improved PCE based on the series was attributed to the more favourable charge separation which was linked to morphology. More recently, Jung et al achieved a PCE of 4.33% using a diketopyrrolopyrrole flanked isoindigo small molecule.…”

Section: Introductionmentioning

confidence: 93%

New 3,3′-(ethane-1,2-diylidene)bis(indolin-2-one) (EBI)-based small molecule semiconductors for organic solar cells

et al. 2017

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A series of donor-acceptor-donor (D-A-D) structured small-molecule compounds, with 3,3'-(ethane-1,2-diylidene)bis(indolin-2-one) (EBI) as a novel electron acceptor building block coupled with various electron donor end-capping moieties (thiophene, bithiophene and benzofuran), were synthesized and characterized. When the fused-ring benzofuran is combined to EBI (EBI-BF), the molecules displayed a perfectly planar conformation and afforded the best charge tranport properties among these EBI compounds with a hole mobility of up to 0.021 cm 2 V -1 s -1 . All EBI-based small molecules were used as donor material along with a PC61BM acceptor for the fabrication of solution-processed bulk-heterojunction (BHJ) solar cells. The best performing photovoltaic devices are based on the EBI derivative using the bithiophene end-capping moiety (EBI-2T) with a maximum power conversion efficiency (PCE) of 1.92%, owing to the broad absorption spectra of EBI-2T and the appropriate morphology of the BHJ. With the aim of establishing a correlation between the molecular structure and the thin film morphology, differential scanning calorimetry, atomic force microscopy and X-ray diffraction analysis were performed on neat and blend films of each material.

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“…Benzene is the most common and widely used fragment in organic semiconductor materials. It has been demonstrated experimentally that a material based on benzene as the central unit has a propeller‐like structure . Moreover, benzene has multiple attachment sites.…”

Section: Star‐shaped Small‐molecule Acceptorsmentioning

confidence: 99%

Star‐Shaped Non‐Fullerene Small Acceptors for Organic Solar Cells

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2019

ChemSusChem

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Over the past decade, organic solar cells (OSCs) have received considerable attention from the scientific community and are considered one of the most important sources of low‐cost electricity production. Recently, OSC‐based on star‐shaped small‐molecule (SM) non‐fullerene acceptors (NFAs) have developed rapidly, and the highest power conversion efficiency (PCE) has exceeded 10 %. The star‐shaped SM NFAs not only have three‐dimensional charge‐transport characteristics similar to fullerenes but also have a strong light absorption capacities and easily tunable energy levels. They are potential candidates as outstanding acceptor materials. In this Review, research progress in of star‐shaped SM NFAs OSCs is reviewed specifically. Moreover, the influence of molecular structure, central unit, and peripheral linking group on OSC performance has been evaluated systematically. This Review could stimulate inspiration for designing high‐performance OSC acceptor materials in the future.

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Linear and propeller-like fluoro-isoindigo based donor–acceptor small molecules for organic solar cells

Cited by 16 publications

References 63 publications

Branched and linear A₂–D–A₁–D–A₂isoindigo-based solution-processable small molecules for organic field-effect transistors and solar cells

Branched and linear A₂–D–A₁–D–A₂isoindigo-based solution-processable small molecules for organic field-effect transistors and solar cells

New 3,3′-(ethane-1,2-diylidene)bis(indolin-2-one) (EBI)-based small molecule semiconductors for organic solar cells

Star‐Shaped Non‐Fullerene Small Acceptors for Organic Solar Cells

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Linear and propeller-like fluoro-isoindigo based donor–acceptor small molecules for organic solar cells

Cited by 16 publications

References 63 publications

Branched and linear A2–D–A1–D–A2isoindigo-based solution-processable small molecules for organic field-effect transistors and solar cells

Branched and linear A2–D–A1–D–A2isoindigo-based solution-processable small molecules for organic field-effect transistors and solar cells

New 3,3′-(ethane-1,2-diylidene)bis(indolin-2-one) (EBI)-based small molecule semiconductors for organic solar cells

Star‐Shaped Non‐Fullerene Small Acceptors for Organic Solar Cells

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Branched and linear A₂–D–A₁–D–A₂isoindigo-based solution-processable small molecules for organic field-effect transistors and solar cells

Branched and linear A₂–D–A₁–D–A₂isoindigo-based solution-processable small molecules for organic field-effect transistors and solar cells