Perspectives on push–pull chromophores derived from click-type [2 + 2] cycloaddition–retroelectrocyclization reactions of electron-rich alkynes and electron-deficient alkenes

• Michio Yamada

Beilstein J. Org. Chem. 2024, 20, 125–154, doi:10.3762/bjoc.20.13

• to posit that the phenyl rings possess a degree of rotational freedom, thereby circumventing steric repulsions. The steric congestion surrounding TCBD moieties can also induce further skeletal rearrangement. For instance, the spatial constraints proximal to the surface of fullerene derivatives lead

• , upon refluxing in chlorobenzene, a rearrangement ensued, yielding tetrakis-substituted fullerene derivatives 33 [112]. During this rearrangement, it was postulated that a zwitterionic intermediate was formed from the nucleophilic attack of the carbon of the dicyanomethylidene adjacent to the DMA group

Controlling the reactivity of La@C₈₂ by reduction: reaction of the La@C₈₂ anion with alkyl halide with high regioselectivity

• Yutaka Maeda,
• Saeka Akita,
• Mitsuaki Suzuki,
• Michio Yamada,
• Takeshi Akasaka,
• Kaoru Kobayashi and
• Shigeru Nagase

Beilstein J. Org. Chem. 2023, 19, 1858–1866, doi:10.3762/bjoc.19.138

• orbital energy gaps owing to their closed shell structures. As previous studies have shown that the absorption spectra of fullerene derivatives sensitively reflect the addition site, the absorption spectra can be regarded as powerful tools to determine the addition site in fullerene adducts [19][23][24

• for La@C2v-C82 anion, and spin densities and POAV values of carbon atoms for La@C2v-C82 [34][35]. The carbon atom numbers correspond to that shown in Figure 6d. Supporting Information Supporting Information features HPLC chromatographs and MS spectra of fullerene derivatives, changes in absorption

[2 + 1] Cycloaddition reactions of fullerene C₆₀ based on diazo compounds

• Yuliya N. Biglova

Beilstein J. Org. Chem. 2021, 17, 630–670, doi:10.3762/bjoc.17.55

• ], have already been discovered among functionalized fullerenes. Bearing in mind the fact that numerous fullerene derivatives with a wide range of biological activity have been synthesized to date, the idea of using functionalized fullerenes in the field of medical chemistry, especially for the treatment

• ]. Fullerene-containing compounds with antiviral (various forms of influenza, herpes, HIV) [28][29][30], antibacterial [31][32][33], and anticancer activity [34][35] have been found among them. An important approach in this area involves the synthesis of complex- and covalent-bound fullerene derivatives with

• fundamentally new architecture appears [38]. The neuroprotective activity of fullerene derivatives may not be ignored either. Encouraging results of their use for the treatment of neurodegenerative pathologies (Alzheimer's and Parkinson's diseases and other diseases accompanied by cognitive impairment) leading

Easy, efficient and versatile one-pot synthesis of Janus-type-substituted fullerenols

• Marius Kunkel and
• Sebastian Polarz

Beilstein J. Org. Chem. 2019, 15, 901–905, doi:10.3762/bjoc.15.87

• steps involved. Fullerene derivatives are of great interest in numerous research areas such as biological sciences and materials sciences [4][5][6][7][8][9]. A vast amount of synthetic protocols have been developed over the years to modify fullerenes [10][11][12][13]. A particular task was to provide

• fullerenes with solubility in water. Thus, one important class of fullerene derivatives are the hydroxylated and polyhydroxylated compounds, so called fullerenols (C60(OH)n) [14]. The degree of hydroxylation and with that the solubility of these compounds can be tuned by using different synthetic approaches

Supramolecular frameworks based on [60]fullerene hexakisadducts

• Andreas Kraft,
• Johannes Stangl,
• Ana-Maria Krause,
• Klaus Müller-Buschbaum and
• Florian Beuerle

Beilstein J. Org. Chem. 2017, 13, 1–9, doi:10.3762/bjoc.13.1

• variety of derivatives have been synthesized as spherical branching units [48][49][50][51][52][53] and, more recently, functionalized fullerene derivatives have been implemented into coordination compounds [54][55][56]. However, to the best of our knowledge, no fullerene-containing crystalline frameworks

• investigations, the implementation of fullerene derivatives possessing long but rigid spacer units might be beneficial for retaining porosity of such supramolecular crystals. Conclusion We have presented the crystallization of two [60]fullerene dodecaacids possessing three-dimensional hydrogen bonding networks

• leads to a Henry behavior in BET investigations. In order to rigidify the structures and stabilize the pore systems upon solvent removal, novel fullerene derivatives possessing less flexible spacers need to be designed and synthesized. Efforts in this regard are currently in progress in our laboratories

Separation and identification of indene–C₇₀ bisadduct isomers

• Bolong Zhang,
• Jegadesan Subbiah,
• David J. Jones and
• Wallace W. H. Wong

Beilstein J. Org. Chem. 2016, 12, 903–911, doi:10.3762/bjoc.12.88

• that the fullerene derivatives in fractions 1 and 9-1 did not have any plane or point of symmetry. The separation mechanism of the Cosmosil Buckyprep-D column is based on the electronic π-orbital interactions between fullerene species and the nitrocarbazoyl-functionalized silica stationary phase [15

• ]. As a consequence, it was envisaged that the fullerene derivatives with smaller π-conjugated area would interact less strongly with the stationary phase of the column and therefore elute faster than derivatives with larger π-surface. In addition, the substitution on fullerenes may block the

• spectrum of the IC70BA fractions. It is widely known that the UV–vis spectrum of fullerene derivatives are highly correlated to their conjugated structures [16]. Therefore, comparison of the UV–vis spectrum of each fraction with known C70 bisadducts, for example the known 2 o’clock-B isomer of IC70BA [9

Enabling technologies and green processes in cyclodextrin chemistry

• Giancarlo Cravotto,
• Marina Caporaso,
• Laszlo Jicsinszky and
• Katia Martina

Beilstein J. Org. Chem. 2016, 12, 278–294, doi:10.3762/bjoc.12.30

• in types 2) and 3) can reduce or eliminate the polluting environment. Reactions of type 1) are dominant in CD/BM literature; more than 98% of publications report the complexation of one or more components. Mechanochemistry opened a new synthetic pathway to the preparation of numerous fullerene

• derivatives by dissolving C60 in the amorphous powder obtained from the ball milled reactants and β-CD [90]. Another example that uses the energy transfer of ball milling is the preparation of MnBi/Fe-Co core/shell structured composites. However, no pure chemical reaction is used to prepare rare-earth free

Novel indolin-2-one-substituted methanofullerenes bearing long n-alkyl chains: synthesis and application in bulk-heterojunction solar cells

• Irina P. Romanova,
• Andrei V. Bogdanov,
• Inessa A. Izdelieva,
• Vasily A. Trukhanov,
• Gulnara R. Shaikhutdinova,
• Dmitry G. Yakhvarov,
• Shamil K. Latypov,
• Vladimir F. Mironov,
• Vladimir A. Dyakov,
• Ilya V. Golovnin,
• Dmitry Yu. Paraschuk and
• Oleg G. Sinyashin

Beilstein J. Org. Chem. 2014, 10, 1121–1128, doi:10.3762/bjoc.10.111

• of low-cost and flexible solar cells [1][2][3]. Organic solar cells are mainly based on bulk heterojunctions composed of a polymer donor and a fullerene acceptor. A number of promising donor materials has been developed, whereas very few successful fullerene derivatives have been proposed. The most

• PSCs. Chlorobenzene is a typical solvent for preparation of PSCs. It is believed that the optimal solubility of fullerene derivatives in chlorobenzene is in the range 30–80 mg·mL−1 at room temperature [16]. It seems that this range of fullerene solubility is needed to provide the optimal bulk

• was served as the working electrode and a Pt wire with a diameter of 1 mm was used as the auxiliary electrode. Measurements were carried out at thermostatic conditions (20 °C) in nitrogen atmosphere. The concentration of the substrate was 5 10−3 M. The LUMO energy levels of the fullerene derivatives

Controlled synthesis of poly(3-hexylthiophene) in continuous flow

• Helga Seyler,
• Jegadesan Subbiah,
• David J. Jones,
• Andrew B. Holmes and
• Wallace W. H. Wong

Beilstein J. Org. Chem. 2013, 9, 1492–1500, doi:10.3762/bjoc.9.170

• mixing of reagents, boosting reaction rates, and safe handling of reactive intermediates. Using a commercial continuous-flow tube reactor [19], we have already demonstrated multigram synthesis of fullerene derivatives by cycloaddition reactions [11] as well as rapid conjugated-polymer synthesis using

Fifty years of oxacalix[3]arenes: A review

• Kevin Cottet,
• Paula M. Marcos and
• Peter J. Cragg

Beilstein J. Org. Chem. 2012, 8, 201–226, doi:10.3762/bjoc.8.22

• to a combination of several factors, of which host–C60 complex formation is only one [77]. Consequently, reported Kassoc values determined by this method should be treated with some caution. Fullerene derivatives that lack some of the symmetry of the parent compound have been shown to bind to

Synthesis of mesogenic phthalocyanine-C₆₀ donor–acceptor dyads designed for molecular heterojunction photovoltaic devices

• Yves Henri Geerts,
• Olivier Debever,
• Claire Amato and
• Sergey Sergeyev

Beilstein J. Org. Chem. 2009, 5, No. 49, doi:10.3762/bjoc.5.49

• fullerene derivatives have been previously reported [40][41][42][43][44], mesogenic Pc-C60 dyads are unknown, most probably due to the tedious purification of the unsymmetrically substituted phthalocyanines bearing long peripheral substituents. A possible elegant solution to this problem was demonstrated by

• given in Hz. MALDI mass spectra were recorded on a Waters MALDI-QTOF Premier, using a 350 mW laser with dithranol (1,8-dihydroxy-10H-anthracen-9-one) as matrix for phthalocyanines and with DCB (trans-2-[3-(4-tert-butylphenyl)-2-methyl-2-propenylidene]malonitrile) as matrix for fullerene derivatives; EI

New diarylmethanofullerene derivatives and their properties for organic thin- film solar cells

• Daisuke Sukeguchi,
• Surya Prakash Singh,
• Mamidi Ramesh Reddy,
• Hideyuki Yoshiyama,
• Rakesh A. Afre,
• Yasuhiko Hayashi,
• Hiroki Inukai,
• Tetsuo Soga,
• Shuichi Nakamura,
• Norio Shibata and
• Takeshi Toru

Beilstein J. Org. Chem. 2009, 5, No. 7, doi:10.3762/bjoc.5.7

• heterojunction solar cells; fullerene derivatives; high open-circuit voltage; Introduction Bulk heterojunction photovoltaic cells consisting of thin-film composites of conjugated polymers (donors) and fullerene derivatives (acceptors) are promising candidates for inexpensive, renewable solar energy conversion

• : 1.135 nm, P-V: 13.47 nm, RMS: 1.573. Synthesis of diarylmethanofullerene derivatives. DPV Data for soluble fullerene derivatives in ODCBa J–V characteristic parameters of bulk–heterojunction solar cells J–V characteristic parameters of P3HT:1a- and P3HT:PCBM-blended solar cells at different annealing

Synthesis of thienyl analogues of PCBM and investigation of morphology of mixtures in P3HT

• Fukashi Matsumoto,
• Kazuyuki Moriwaki,
• Yuko Takao and
• Toshinobu Ohno

Beilstein J. Org. Chem. 2008, 4, No. 33, doi:10.3762/bjoc.4.33

• ]. Recently, bulk heterojunction solar cells consisting of a conjugated polymer (donor) and fullerene derivatives (acceptors) have inspired much scientific research owing to these reasons [8][9]. In this research, it has been demonstrated that the PV cells based on regio-regular poly(3-hexylthiophene) (P3HT

• exploring new acceptor materials have not been performed. In particular, there is no research focusing on how the structure of fullerene derivatives affects the morphology of the active layer of a PV device. However, it is essential to explore novel fullerene derivatives in order to achieve a significant

• . Solubility of methanofullerenes Good solubility of fullerenes is important for fabricating a photovoltaic device with good morphology [24]. In fact, PCBM is one of the most soluble fullerene derivatives and this is the main reason why it is used for the fabrication of PV cells. Chlorobenzene is normally used