160848-22-6Relevant articles and documents
Facile synthesis of methanofullerenes in an aqueous two-phase system under photoirradiation conditions
Iwai, Toshiyuki,Matsumoto, Fukashi,Hida, Koichi,Moriwaki, Kazuyuki,Takao, Yuko,Ito, Takatoshi,Mizuno, Takumi,Ohno, Toshinobu
, p. 960 - 964 (2015)
Methanofullerenes, such as [6,6]-phenyl-C61-butyric acid methyl ester {[6,6]PC61BM (1a)}, were synthesized in good yields from the corresponding tosylhydrazones in an aqueous two-phase (o-dichlorobenzene-H2O) system under
Continuous flow synthesis of fullerene derivatives
Seyler, Helga,Wong, Wallace W. H.,Jones, David J.,Holmes, Andrew B.
, p. 3551 - 3556 (2011)
Various fullerene-based electron acceptor materials for organic photovoltaic applications were prepared via [3 + 2] and [4 + 2] cycloadditions using a continuous flow approach. The 1,3-dipolar cycloaddition of the tosylhydrazone precursor and the Diels-Alder cycloaddition of indene to either C60 or C70 under conventional batch reaction conditions were translated to the continuous flow process. By varying the residence time, temperature, and equivalents of cycloaddition reagent, significant improvements in yields and reaction times were achieved over conventional batch processes.
Efficient microwave-mediated synthesis of fullerene acceptors for organic photovoltaics
Campisciano, Vincenzo,Riela, Serena,Noto, Renato,Gruttadauria, Michelangelo,Giacalone, Francesco
, p. 63200 - 63207 (2014)
Two different processes, namely the Bamford-Stevens and [4 + 2] Diels Alder reactions, have been optimized under microwave irradiation for the functionalization of fullerenes. In this manner, all the main C60- and C70-based acceptor derivatives for organic solar cells such as PCBM, DPM, BHN and ICBA, have been prepared in higher yields and shorter reaction times with respect to the reported data. These findings represent a step forward toward the wide production of cheaper organic solar cells as a consequence of the cost abatement of the acceptors given by higher yields, lower waste production, and reduced reaction time which means a strong energy saving.
Preparation and Characterization of Fulleroid and Methanofullerene Derivatives
Hummelen, Jan C.,Knight, Brian W.,LePeq, F.,Wudl, Fred,Yao, Jie,Wilkins, Charles L.
, p. 532 - 538 (1995)
We describe the synthesis and complete characterization of soluble derivatives of C60 for applications to physics and biology.The goal of the strategy was to have a "modular" approach in order to be able to easily vary a functional group attached indirectly to the cluster.The functionality could be hydrophilic (e.g., histamide) or hydrophobic (e.g., cholestanoxy).The former was prepared for biological studies and the latter for photophysical studies toward improvement of photoinduced electron transfer efficiencies in the fabrication of photodetectors and photodiodes.An important intermediate, a carboxylic acid, was found to be recalcitrant to characterization by the usual mass spectroscopic and elemental analysis techniques.This problem was solved by the use of MALDI-MS.The carboxylic acid was easily converted to the key intermediate acid chloride, which in turn was convertible to a large variety of derivatives.Both isomeric forms (, fulleroid and , methanofullerene) of the C61 clusters were prepared.The fulleroid formation could have given rise to a 50:50 mixture of phenyl-over-former pentagon phenyl-over-former hexagon isomers but, remarkably, afforded a 95:5 mixture of these isomers, respectively.The fulleroid and methanofullerene gave different cyclic voltammograms, with the former being reduced at 34 mV more positive potential than the latter.
Efficient microwave-assisted synthesis of PCBM methanofullerenes (C60 and C70)
Hadad, Caroline,Syrgiannis, Zois,Bonasera, Aurelio,Prato, Maurizio
, p. 1423 - 1427 (2015)
PCBM is a fullerene derivative (phenyl-C61-butyric acid methyl ester) considered to be one of the best n-type organic semiconductors and plays a relevant role in organic photovoltaic solar cells. Much effort has been devoted to the optimization of the synthesis of PCBM derivatives. In this paper, PC61BM and PC71BM fullerene mono-adducts but also PCBM-like derivatives are successfully prepared by a one- step cyclopropanation reaction under microwave irradiation. The products are collected in good yields in short time, during which isomerization of the open [5,6] to the closed [6,6] form takes place in situ. In addition, with the use of two cycles of irradiation, a series of mixtures of bis-adduct PCBM-like derivatives were also obtained in good yields.
A dimeric fullerene derivative for efficient inverted planar perovskite solar cells with improved stability
Tian, Chengbo,Kochiss, Kevin,Castro, Edison,Betancourt-Solis, German,Han, Hongwei,Echegoyen, Luis
, p. 7326 - 7332 (2017)
Fullerene derivatives can efficiently passivate the interfacial defects of perovskite layers to improve the performance of perovskite solar cells. In this work, a new dimeric fullerene derivative (D-C60) with two [6,6]-phenyl-C61-butyric acid methyl ester (PC61BM) units was designed, synthesized and applied as the electron transporting material (ETM) in perovskite solar cells (PSCs) taking advantage of its appropriate energy levels, relatively fast electron mobility, and easy solution processability compared to the widely used PC61BM, D-C60 can efficiently passivate the trap states between the perovskite and fullerene layers, leading to improved electron extraction and overall photovoltaic performance. Devices based on D-C60 as the ETM achieved power conversion efficiencies (PCEs) of 16.6%, which is significantly higher than that observed with PC61BM (14.7%). In addition, the more hydrophobic and compact D-C60 layer resulted in higher device stability than that with PC61BM. These results show that covalently linked dimeric fullerene derivative can act as efficient electron transporting materials (ETMs) for high performance PSCs.
Rigidified tetrathiafulvalene-[60]fullerene assemblies: Towards the control of through-space orientation between both electroactive units
Kreher, David,Cariou, Michel,Liu, Sheng-Gao,Levillain, Eric,Veciana, Jaume,Rovira, Concepcio,Gorgues, Alain,Hudhomme, Pietrick
, p. 2137 - 2159 (2002)
Our recent works on fused TTF-C60 dyads, (TTF)n-C60 polyads and C60-TTF-C60 dumbbell triads in which the acceptor C60 is doubly tethered to the donor tetrathiafulvalene through a rigidified
Methanofullerene Synthesis via Photogenerated Fullerene Radical Anion Intermediates
Ito, Takatoshi,Iwai, Toshiyuki,Matsumoto, Fukashi,Sumino, Shuhei
, p. 8500 - 8507 (2021/06/28)
This work describes the synthesis of PCBM ([6,6]-phenyl-C61-butyric acid methyl ester) derivatives and other methanofullerene derivatives via generation of fullerene radical anions under photoirradiation and controlled by photoswitching, without preparation, a strong reducing agent, or precise control of the reaction conditions.
Fullerene derivative and application thereof in perovskite solar cell
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Paragraph 0083-0086, (2017/07/12)
The invention discloses a fullerene derivative and an application thereof in a perovskite solar cell. The structural formula of the fullerene derivative is shown in the specification. The fullerene derivative disclosed by the invention has relatively good solubility and relatively high LUMO energy level and can be applied to a solar cell device as an electron transport layer so that the device has relatively high open-circuit voltage and fill factor, relatively high photoelectric conversion efficiency, no hysteresis effect and relatively good application prospect; and meanwhile, a preparation method of the fullerene derivative provided by the invention has the advantages of easiness in synthesis, relatively high yield and relatively low cost and is very conducive to commercial production.
Facile synthesis of [6,6]-phenyl-C61/71-butyric acid methyl esters via sulfur ylides for bulk-heterojunction solar cell
Ito, Takatoshi,Iwai, Toshiyuki,Matsumoto, Fukashi,Hida, Koichi,Moriwaki, Kazuyuki,Takao, Yuko,Mizuno, Takumi,Ohno, Toshinobu
, p. 1988 - 1992 (2013/09/24)
A one-step, mild synthesis of methanofullerenes as electron acceptors for solution-processed bulk-heterojunction solar cells was developed. [6,6]-Phenyl-C61-butyric acid methyl ester {[60]PCBM} was directly synthesized in good yields, by the reaction of fullerene with sulfur ylide derivatives in the presence of 1,8-diazabicyclo-[5.4.0]undec-7-ene (DBU) at room temperature. This method was also successfully applied to the preparation of [6,6]-phenyl-C71-butyric acid methyl ester {[70]PCBM}. Georg Thieme Verlag Stuttgart, New York.
