Article
Chemistry, Multidisciplinary
Kevin Grollier, Arnaud De Zordo-Banliat, Flavien Bourdreux, Bruce Pegot, Guillaume Dagousset, Emmanuel Magnier, Thierry Billard
Summary: This study presents a method for synthesizing molecules bearing (trifluoromethylselenyl)methylchalcogenyl groups, with good yields up to 88% and up to 98% in flow chemistry conditions. The mechanism of this key reaction was investigated, and the emerging groups were physicochemically characterized. Additionally, the reaction was extended to perfluoroalkylselenolation with yields up to 95%, and successfully applied to the functionalization of bioactive molecules.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Yuki Arakawa, Yuko Ishida, Takuma Shiba, Kazunobu Igawa, Shunsuke Sasaki, Hideto Tsuji
Summary: The alkylthio groups mainly decrease phase transition temperatures, especially T-NI or T-IN, and hinder liquid crystal formation for organic rod-like molecules, primarily due to conformational flexibility, steric bulkiness, and lower molecular anisotropy imposed by C-S-C. The sulfur atom contributes to intermolecular attractive interactions, reflected in phase transitions as spatially averaged phenomena (i.e., dispersion force and more polarizable pi-systems). The influence of these interactions becomes more pronounced with lengthening alkyl chains.
Article
Chemistry, Multidisciplinary
Hikaru Yanai, Shoki Hoshikawa, Yukiko Moriiwa, Atsushi Shoji, Akio Yanagida, Takashi Matsumoto
Summary: A new method has been developed to introduce a stable carbanionic substituent into various fluorescence dyes, resulting in significantly enhanced water solubility and lipophilicity. This work demonstrates the potential of fluorinated, highly stabilized carbanionic substituents as a new option for controlling the macroscopic properties of chemical materials.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Sigal Saphier, Shahaf Katalan, Guy Yacov, Anat Berliner, Orit Redy-Keisar, Gil Fridkin, Lee Ghindes-Azaria, Ishay Columbus, Alexander Pevzner, Eyal Drug, Hagit Prihed, Eytan Gershonov, Yoav Eichen, Shlomi Elias, Galit Parvari, Yossi Zafrani
Summary: Fluorine atoms play an important role in chemistry, and studying their effects on the structure-physicochemical properties relationship is crucial. This study explores the exceptional physicochemical effects resulting from H/F exchange in gem-difunctional compounds. The lipophilicity change observed for CH2/CF2 replacement far exceeds expectations. Additionally, the effect is nearly additive for compounds with multiple gem-difunctional moieties, allowing for a switch from hydrophilic to lipophilic with just a few H/F exchanges. DFT studies reveal that polarity, conformational preference, and charge distributions are strongly affected by hydrogen to fluorine atom substitution. These pronounced effects, achieved with low cost in terms of molecular weight or steric effects, have great potential in various fields of chemical sciences.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Biochemistry & Molecular Biology
Igor E. Mikhnovets, Jiri Holoubek, Irina S. Panina, Jan Kotoucek, Daniil A. Gvozdev, Stepan P. Chumakov, Maxim S. Krasilnikov, Mikhail Y. Zhitlov, Evgeny L. Gulyak, Alexey A. Chistov, Timofei D. Nikitin, Vladimir A. Korshun, Roman G. Efremov, Vera A. Alferova, Daniel Ruzek, Ludek Eyer, Alexey V. Ustinov
Summary: Amphipathic perylene derivatives are effective antiviral compounds that target the viral envelope and act as fusion inhibitors. They damage the viral envelope using lipophilic perylene and singlet oxygen generated by light. Short alkyl chains contribute to strong antiviral activity, while longer alkyl chains reduce activity due to increased lipophilicity and aggregation.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Chemistry, Physical
Sabtanti Harimurti, Wasiti Puji Rahayu, Hayu Ikfini, Hari Widada, Salmah Orbayinah, Andy Eko Wibowo, Kiki Adi Kurnia
Summary: This study aims to determine the effectiveness of re-maceration on the purification of GVT-0 and the impact of pH and the polarity index of organic solvents on the partition coefficient. The results show that the purification process was successful and pH values and solvent polarity index have an effect on the partition coefficient.
JOURNAL OF MOLECULAR STRUCTURE
(2024)
Article
Chemistry, Multidisciplinary
Vladislav S. Kostromitin, Artem O. Sorokin, Vitalij V. Levin, Alexander D. Dilman
Summary: Readily available 1,3,5-trimethyl-1,3,5-triazinane acts as an efficient reagent for halogen atom transfer, generating an alpha-aminoalkyl radical under photocatalytic conditions to activate C-Cl bonds of fluorinated alkyl chlorides. The article describes the hydrofluoroalkylation reaction between fluorinated alkyl chlorides and alkenes. The efficiency of the diamino-substituted radical derived from the triazinane is determined by a stereoelectronic effect involving a six-membered cycle that enforces an anti-periplanar arrangement of the radical orbital and lone pairs of adjacent nitrogen atoms.
Article
Biotechnology & Applied Microbiology
Quinn T. Birch, Mary E. Birch, Mallikarjuna N. Nadagouda, Dionysios D. Dionysiou
Summary: This paper discusses the application of nanoscale technologies in the treatment of water contamination, providing new methods and opportunities for dealing with per-fluorinated and poly-fluorinated alkyl substances (PFAS).
CURRENT OPINION IN CHEMICAL ENGINEERING
(2022)
Article
Chemistry, Physical
Yuzhong Chen, Fujin Bai, Zhengxing Peng, Lei Zhu, Jianquan Zhang, Xinhui Zou, Yunpeng Qin, Ha Kyung Kim, Jun Yuan, Lik-Kuen Ma, Jie Zhang, Han Yu, Philip C. Y. Chow, Fei Huang, Yingping Zou, Harald Ade, Feng Liu, He Yan
Summary: The paper presents a strategy of asymmetric alkyl and alkoxy substitution on Y-series nonfullerene acceptors, achieving great performance in organic solar cell devices. Asymmetric substitution on Y6 results in a molecule that maintains V-oc improvement and good solubility, enabling highly efficient nonfullerene OSCs. This asymmetric side-chain strategy shows potential for improving the performance of other NFA-material systems.
ADVANCED ENERGY MATERIALS
(2021)
Article
Chemistry, Organic
A'lvaro Gutierrez-Bonet, Wenbin Liu
Summary: Using alpha-fluoroalkyl or fluorobenzyl radicals generated from easily accessible alpha-fluorocarboxylic acids, we achieved the rapid synthesis of fluorine-containing building blocks through Giese-type addition reactions. This method allows for the preparation of mono- and difluorinated Michael addition adducts as well as unnatural fluorinated amino acids under mild reaction conditions.
Article
Food Science & Technology
Yan Xu, Jing Zhang, Teng Pan, Fazheng Ren, Hailing Luo, Hao Zhang
Summary: By acylating chlorogenic acid (CGA) with fatty acids of different unsaturation degrees, its lipophilicity was improved and antioxidant activity was enhanced. The acylated CGA derivatives showed potential as antioxidants for lipophilic food systems.
LWT-FOOD SCIENCE AND TECHNOLOGY
(2022)
Article
Engineering, Electrical & Electronic
Ting Luo, Wei-Wang Zeng, Ruidan Zhang, Chuanyao Zhou, Xueming Yang, Zefeng Ren
Summary: A simple and environmentally friendly method for hydrophobic modification on silica surfaces was proposed by grafting alkoxy groups on the surfaces via alcohol alkoxylation reaction. The modified silica surface showed a water contact angle larger than 90 degrees, indicating its potential to replace traditional surface modification processes using silane adhesives in industry.
ACS APPLIED ELECTRONIC MATERIALS
(2021)
Article
Chemistry, Multidisciplinary
Leonie J. Bole, Neil R. Judge, Eva Hevia
Summary: This study describes the activation of sBu(2)Mg towards substituted bromoarenes by adding LiOR (R=2-ethylhexyl), leading to the formation of two different types of organometallic intermediates. NMR spectroscopic studies reveal that the exchange reactions and the formation of intermediates are controlled by a new type of bimetallic Schlenk-type equilibrium.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Xinyi Ren, Zhen Wang, Chaoren Shen, Xinxin Tian, Lin Tang, Xiaolei Ji, Kaiwu Dong
Summary: A highly efficient method for asymmetric carbonylation reactions has been developed in this study, allowing for the synthesis of chiral molecules with high optical purity from beta-carbonyl functionalized alkenes. This method features mild reaction conditions and a broad substrate scope, and has the potential for further applications in catalytic asymmetric carbonylation reactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Tanja Knuplez, Leon N. Schneider, Tobias Preitschopf, Younes K. J. Bejaoui, Ludwig Zapf, Nils Schopper, Kristina A. M. Maibom, Jan A. P. Sprenger, Franziska Gehrke, Sabine Lorenzen, Roland Graf, Ruediger Bertermann, Ingo Fischer, Nikolai V. Ignat'ev, Maik Finze
Summary: This study presents a scalable and straightforward synthesis method for monofluoro- and difluoromethyl triflates through electrochemical fluorination. The method is also applicable for the preparation of deuterated analogues. The study also provides detailed spectroscopic, structural, and thermal data on (fluoro)methyl and fluoro(ethyl) triflates.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)