Article
Chemistry, Organic
Yue Sun, Cheng Qian, Thomas J. Emge, Yanbang Li, William P. Kopcha, Lu Wang, Jianyuan Zhang
Summary: This study reports the oxidative [4 + 2] reaction of o-phenylenediamine-derived disulfonamides with fullerene C-60 and C-70. The reactants with electron deficiency showed high reactivity. The reaction of C-70 exhibited unusual regioselectivity, yielding a [5,6]-adduct as the major product, which was characterized by experimental and computational methods.
Article
Chemistry, Multidisciplinary
Jinliang Ma, Tong-Xin Liu, Pengling Zhang, Chuanjie Zhang, Guisheng Zhang
Summary: A new, general, and practical method for the spirocyclization of [60]fullerene has been presented through a palladium-catalyzed domino Heck/C-H activation reaction. A wide range of novel [60]fullerene-fused spirocyclic derivatives can be easily synthesized with broad substrate scope and excellent functional-group tolerance. A plausible mechanism involving an alkyl Pd(ii) species as a key intermediate has been proposed.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Inorganic & Nuclear
Yoshifumi Hashikawa, Nana Fujikawa, Shu Okamoto, Yasujiro Murata
Summary: The chemical stability of phosphorus ylides is significantly lowered when a carbonyl group in cage-opened C60 derivatives is replaced with a sulphide moiety, resulting in in situ hydrolysis and the formation of an alpha-methylene carbonyl compound. This change also causes a hypsochromic shift in the near-infrared absorption band.
DALTON TRANSACTIONS
(2022)
Article
Biochemistry & Molecular Biology
Piotr Piotrowski, Wojciech Mech, Kamila Zarebska, Maciej Krajewski, Krzysztof P. Korona, Maria Kaminska, Magdalena Skompska, Andrzej Kaim
Summary: In this study, six (two new) fullerene mono- and di-pyrene derivatives based on C-60 and C-70 fullerenes were successfully synthesized and characterized using spectral methods and cyclic voltammetry. The efficiency of solar cells made of these derivatives was analyzed, and it was found that the electronic and spectral properties of the derivatives, as well as the homogeneity of the photovoltaic layer, play a crucial role in determining the efficiency of the constructed solar cells.
Article
Chemistry, Organic
Nikitas G. Malliaros, Ina D. Kellner, Thomas Drewello, Michael Orfanopoulos
Summary: A new one-step method for functionalizing C-60 with lactones has been developed, leading to the synthesis of a previously unknown class of materials, namely 1-lactonyl-2-hydro[60]fullerenes. The mechanism of this reaction has been proposed based on the structure of reaction products and deuterium-incorporated experiments.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Kyangzi Calderon-Cerquera, Alejandra Parra, Duvalier Madrid-Usuga, Andrea Cabrera-Espinoza, Carlos A. Melo-Luna, John H. Reina, Braulio Insuasty, Alejandro Ortiz
Summary: The novel compounds BDP(Pyr)2 and BDP(Iso)2 show strong interaction in the excited state, generating charged species between BODIPY and the two C-60 units. The electronic interaction is stronger in BDP(Iso)2 than in BDP(Pyr)2, likely due to isoxazoline ring conjugation. Fluorescence lifetime measurements confirm that BDP(Iso)2 performs better even at different solvent polarities.
Article
Chemistry, Multidisciplinary
Shumpei Sadai, Yoshifumi Hashikawa, Yasujiro Murata
Summary: Two open-[60]fullerene-aniline conjugates were synthesized by incorporating diamine into [60]fullerene, resulting in the formation of thiazolidine-2-thione ring in the presence of CS2. The absorption edge was significantly shifted to 1200 nm by increasing the number of N,N-dimethylaniline moieties, indicating strong acceptor-donor interactions.
Article
Chemistry, Organic
Zhan Liu, Zheng-Chun Yin, Wen-Qiang Lu, Chuang Niu, Muqing Chen, Shangfeng Yang, Guan-Wu Wang
Summary: A novel and efficient Cu(I)-catalyzed radical heteroannulation reaction of [60]fullerene with alpha-bromo acetamides has been developed for the direct synthesis of diverse C-60-fused lactams. The C-60-fused lactams can further undergo electrochemical functionalization to prepare various adducts of C-60, and a representative fullerene product has been utilized as an overcoating layer in n-type perovskite solar cells.
Article
Chemistry, Organic
Di Chao, Tong-Xin Liu, Pengling Zhang, Shilu Xia, Guisheng Zhang
Summary: An unexpected copper-mediated radical-induced ring-opening relay cascade carboannulation reaction of [60]fullerene with cyclobutanone oxime esters is presented for the preparation of various Cl-/Br-incorporated [60]fullerene-fused cyclopentanes. The unique relay cascade transformation uses inexpensive copper salts as promoters and halogen sources and features simple redox-neutral conditions and a broad substrate scope, providing a practical access to a class of novel five-membered carbocycle-fused fullerenes.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Jinliang Ma, Tong-Xin Liu, Pengling Zhang, Xuna Zhao, Guisheng Zhang
Summary: A metal-free-catalyzed multicomponent annulation reaction using I2 as a catalyst has been developed for the construction of novel [60]fullerene-fused 1,2-tetrahydrocarbazoles. Mechanistic studies indicate that the reaction proceeds through I2-promoted generation of a 3-vinylindole structure followed by cycloaddition to [60]fullerene.
Article
Chemistry, Organic
Yi-Tan Su, Zheng-Chun Yin, Guan-Wu Wang
Summary: In this study, a palladium-catalyzed three-component alkoxyarylation reaction was conducted to synthesize a series of 1,4-(alkoxy)(aryl)[60]fullerene derivatives. Plausible reaction pathways for the formation of 1,4-(alkoxy)(aryl)[60]fullerenes were proposed. The electrochemical properties of the synthesized adducts were also investigated.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Rodrigo Alexandre Ferreira, Jeziel Rodrigues dos Santos, Jussara Miguel Falleiros, Elson Longo da Silva, Jose Divino dos Santos
Summary: Theoretical study on the fullerothiazolidinethione structures functionalized with R-thiazolidinethione showed increased dipole moment, higher solubility in polar solvents, and enhanced stability of the formed structures, as analyzed using density functional theory.
CHEMICAL PHYSICS LETTERS
(2021)
Article
Chemistry, Organic
Chuang Niu, Zhiwei Xu, Xinmin Huang, Wei-Feng Wang, Zheng-Chun Yin, Guan-Wu Wang
Summary: The efficient electrosynthesis of decorated basket molecules, specifically [60]fullerene-fused 12-membered macrolactones, has been achieved for the first time. This was done through the electrochemical reduction of [60]fullerene-fused 6-membered lactones followed by ring expansion with 1,2-bis(1-bromoalkyl)benzenes. The isomeric distributions of the obtained macrolactones were elucidated through theoretical calculations, and the product structures were established through single-crystal X-ray analyses.
Article
Chemistry, Multidisciplinary
Zhan Liu, Zheng-Chun Yin, Wen-Qiang Lu, Dian-Bing Zhou, Guan-Wu Wang
Summary: In this study, an unexpected Diels-Alder reaction of [60]fullerene (C-60) with ferrocenes bearing electron-withdrawing groups as cyclopentadiene surrogates was developed to selectively afford single isomers of [2 + 4] cycloadducts of C-60. Mechanistic studies showed the in situ generation of cyclopentadienes from electron-deficient ferrocenes in the presence of an oxidant and an acid, followed by [2 + 4] cycloadditions with dienophiles. A Michael addition reaction using a Grignard reagent was utilized to transform the Diels-Alder adducts of C-60 into more stable fullerene derivatives.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Yoshifumi Hashikawa, Shumpei Sadai, Yasujiro Murata
Summary: In this study, we achieved bilateral pi-elongation in open-[60]fullerenes through consecutive nucleophilic additions at another site. The resulting pi-extended open-[60]fullerene contains two diaza[n]helicene (n = 5 and 6) motifs in its skeleton. Crystallographic analysis revealed close contacts of 3.09 and 3.14 angstrom between the helicene and fullerene.
CHEMICAL COMMUNICATIONS
(2023)
