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.
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.
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.
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.
