Review: Fullerene based acceptors for efficient bulk heterojunction organic solar cell applications

Ganesamoorthy, Ramasamy; Sathiyan, Govindasamy; Sakthivel, Pachagounder

doi:10.1016/j.solmat.2016.11.024

Cited by 284 publications

(198 citation statements)

References 191 publications

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“…[1][2][3][4][5][6][7] To facilitate that task, a multitude of diverse fullerene functionalization techniques have been developed in the last two decades. [1][2][3][4][5][6][7] To facilitate that task, a multitude of diverse fullerene functionalization techniques have been developed in the last two decades.…”

Section: Introductionmentioning

confidence: 99%

Regioselective Synthesis of [6,6]‐Open and [5,6]‐Closed C₇₀(CF₃)₈[CH₂] Methanofullerenes with Rapid [6,6]‐to‐[5,6] Phototransformation

et al. 2018

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Fullerene derivatives with >CH2 addends in [6,6]‐open or [5,6]‐closed configuration are uncommon of fullerene derivatives, but they are readily accessible via treatment of Cs‐C70(CF3)8 with diazomethane followed by thermolysis or photolysis. Both thermodynamic and kinetic factors favor regioselective addition of diazomethane at the near‐equatorial [5,6]‐double bond of Cs‐C70(CF3)8 to give a thermally labile pyrazoline intermediate. Thermal extrusion of N2 from the latter is a kinetically controlled process with orbital symmetry controlled Woodward–Hoffmann‐allowed mechanism. It quantitatively yields the less thermodynamically favorable [6,6]‐open isomer of C70(CF3)8[CH2] homofullerene, but the latter turns out to be capable of unexpectedly rapid quantitative phototransformation into the thermodynamically preferable [5,6]‐closed methanofullerene isomer. The transformation involves the manifold of the triplet states that facilitate the required cleavage of the Ccage–CH2 bonds.

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Section: Introductionmentioning

confidence: 99%

Regioselective Synthesis of [6,6]‐Open and [5,6]‐Closed C₇₀(CF₃)₈[CH₂] Methanofullerenes with Rapid [6,6]‐to‐[5,6] Phototransformation

et al. 2018

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“…[1][2][3][4][5] The photoactive layer generally comprises a blend lm with a bulk heterojunction (BHJ) structure of electron-donating conjugated polymers and electron-accepting organic semiconductors. Fullerene derivatives have been widely utilized as electron-acceptors 5 because of their reversible reduction behaviors, outstanding electron affinities, and excellent electron-transporting properties originating from their small reorganization energies of electron transfer, 6 whereas non-fullerene electron acceptors, exhibiting high power conversion efficiencies (PCEs), have recently emerged as alternatives.…”

Section: Introductionmentioning

confidence: 99%

cis-1 Isomers of tethered bismethano[70]fullerene as electron acceptors in organic photovoltaics

et al. 2018

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Isomer-controlled [70]fullerene bis-adducts can achieve high performance as electron-acceptors in organic photovoltaics (OPVs) because of their stronger absorption intensities than [60]fullerene derivatives, higher LUMO energy levels than mono-adducts, and less structural and energetic disorder than random isomer mixtures. Especially, attractive are cis-1 isomers that have the closest proximity of addends owing to their plausible more regular close packed structure. In this study, propylene-tethered cis-1 bismethano[70]fullerene with two methyl, ethyl, phenyl, or thienyl groups were rationally designed and prepared for the first time to investigate the OPV performances with an amorphous conjugated polymer donor (PCDTBT). The cis-1 products were found to be a mixture of two regioisomers, a-1-a and a-1-b as major and minor components, respectively. Among them, the cis-1 product with two ethyl groups (Et 2 -cis-1-[70]PBC) showed the highest OPV performance, encouraging us to isolate its a- fullerene bis-adducts do not guarantee better OPV performance and that further optimization of the substituent structures is necessary. 1-a isomer (Et

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“…The bulk heterojunction (BHJ) organic solar cell (OSC) device comprises a blend of electron donor polymer and fullerene acceptor materials sandwiched between the hole and electron selective electrodes, and is a potential alternative to high cost silicon based solar cells due to its printable, portable, low‐cost and flexible renewable energy source . From poly(3‐hexylthiophene) (P3HT) to many recent low band gap polymer donors with the benchmark [6,6]‐phenyl‐C 61 ‐butyric acid methyl ester (PC 61 BM) or [6,6]‐phenyl‐C 71 ‐butyric acid methyl ester (PC 71 BM) acceptors in the active layer, BHJ OSC devices have reached a maximum power conversion efficiency (PCE) of 10%–11% .…”

Section: Introductionmentioning

confidence: 99%

[60]Fullerene‐quinoxaline, benzothiadiazole and benzoselenadiazole based dyads for thermally stable polymer solar cells: anchoring of substituent on fullerene with a poly(3‐hexylthiophene) polymer chain

Elavarasan¹,

Saravanan²,

Selvam³

et al. 2018

Polymer International

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[6,6]‐Phenyl‐C61‐butyric acid methyl ester (PC61BM and PC71BM) is an archetypal electron acceptor in organic photovoltaic devices. However, it nucleates and grows to form aggregates or crystallites on a length scale of tens of nanometres to micrometres under thermal aging, which often results in a significant decrease in device efficiency and stability. To overcome this thermally induced performance degradation, many methods have been reported to date such as the introduction of hydrogen, halogen bonding, thermally or photochemically crosslinkable groups onto the fullerene, and the suppression of nucleation and growth of fullerene crystallites under thermal aging has been successfully demonstrated. Even though those methods are highly useful for the suppression of aggregation, we successfully demonstrated another one simple method for the same: Introduction of bulkier groups onto the fullerene, which can act as anchoring group to suppress the aggregation. In an extension of our previous work, quinoxaline (TQT), benzothiadiazole (TBTT) and benzoselenadiazole (TBST) based bulkier groups are linked to the fullerene, denoted as TQT‐C60, TBTT‐C60 and TBST‐C60, respectively, through the 1,3‐dipolar cycloaddition of corresponding azomethine ylides with fullerene. Single junction bulk heterojunction polymer solar cells were fabricated with the configuration ITO/PEDOT:PSS/P3HT:dyad/Ca/Al. The morphological stability of the active layer was monitored by transmission electron microscopy and optical microscopy. Independent of heteroatoms, all the dyads show excellent morphological stability under thermal aging compared to the archetypal acceptor PCBM due to the anchoring of substituent groups. © 2018 Society of Chemical Industry

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Review: Fullerene based acceptors for efficient bulk heterojunction organic solar cell applications

Cited by 284 publications

References 191 publications

Regioselective Synthesis of [6,6]‐Open and [5,6]‐Closed C₇₀(CF₃)₈[CH₂] Methanofullerenes with Rapid [6,6]‐to‐[5,6] Phototransformation

Regioselective Synthesis of [6,6]‐Open and [5,6]‐Closed C₇₀(CF₃)₈[CH₂] Methanofullerenes with Rapid [6,6]‐to‐[5,6] Phototransformation

cis-1 Isomers of tethered bismethano[70]fullerene as electron acceptors in organic photovoltaics

[60]Fullerene‐quinoxaline, benzothiadiazole and benzoselenadiazole based dyads for thermally stable polymer solar cells: anchoring of substituent on fullerene with a poly(3‐hexylthiophene) polymer chain

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Review: Fullerene based acceptors for efficient bulk heterojunction organic solar cell applications

Cited by 284 publications

References 191 publications

Regioselective Synthesis of [6,6]‐Open and [5,6]‐Closed C70(CF3)8[CH2] Methanofullerenes with Rapid [6,6]‐to‐[5,6] Phototransformation

Regioselective Synthesis of [6,6]‐Open and [5,6]‐Closed C70(CF3)8[CH2] Methanofullerenes with Rapid [6,6]‐to‐[5,6] Phototransformation

cis-1 Isomers of tethered bismethano[70]fullerene as electron acceptors in organic photovoltaics

[60]Fullerene‐quinoxaline, benzothiadiazole and benzoselenadiazole based dyads for thermally stable polymer solar cells: anchoring of substituent on fullerene with a poly(3‐hexylthiophene) polymer chain

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Regioselective Synthesis of [6,6]‐Open and [5,6]‐Closed C₇₀(CF₃)₈[CH₂] Methanofullerenes with Rapid [6,6]‐to‐[5,6] Phototransformation

Regioselective Synthesis of [6,6]‐Open and [5,6]‐Closed C₇₀(CF₃)₈[CH₂] Methanofullerenes with Rapid [6,6]‐to‐[5,6] Phototransformation