Article
Biochemistry & Molecular Biology
Fengxi Li, Yaning Xu, Ciduo Wang, Chunyu Wang, Ruihong Zhao, Lei Wang
Summary: A green and efficient process for the synthesis of Indoles from 1,3-diketones with fumaronitrile was developed in this study. When using CRL as the catalyst, high yields and satisfactory regioselectivity of cyano-containing multi-substituted indoles could be obtained. This enzymatic method demonstrates the great potential for the synthesis of indoles and extends the application of enzyme in organic synthesis.
BIOORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Francesca Arcudi, Andrea Sartorel, Anna Fortunato, Tomas Marangoni, Nicola Demitri, Michele Maggini, Luka Dordevic
Summary: A new triflatophenylporphyrin building block for Pd-catalyzed cross-coupling reactions is proposed. Compared to halophenylporphyrins, its purification is much easier. The triflatophenylporphyrin is also suitable in microwave-assisted Sonogashira cross-coupling and has been used to prepare a donor-acceptor array.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Achraf El Hallaoui, Youssef Merroun, Soukaina Chehab, Said Boukhris, Hicham Hassoune, Rachida Ghailane, Abedelaziz Souizi
Summary: This study presents a new environmentally sustainable catalytic method for the synthesis of symmetrically substituted pyridine derivatives and substituted alkene derivatives using zinc phosphate (Zn-3(PO4)(2)& BULL;4H(2)O) as a non-toxic and green heterogeneous catalyst. Trisubstituted pyridine derivatives were prepared with excellent yields (82-94%) via a three-component, one-pot synthesis of aromatic aldehydes, substituted acetophenones, and ammonium acetate in the presence of 0.4 mol% of Zn-3(PO4)(2)& BULL;4H(2)O using an ethanol/water (4/1) mixture as the solvent, while substituted alkenes were synthesized with up to 90% yield using the prepared catalyst. The experimental results demonstrate the efficiency of these new catalytic syntheses that present various advantages such as short reaction times, excellent yields, and an environmentally friendly profile.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Kazuki Tomota, Yuki Izumi, Kazuki Nakanishi, Masaaki Nakamoto, Hiroto Yoshida
Summary: A direct and transition metal-free method for the installation of B(dan) into organic frameworks has been developed. Heteroaryl-H bonds can be transformed into heteroaryl-B(dan) bonds through deprotonation. The resulting heteroaryl-B(dan) compounds, which are typically difficult to access, can undergo direct Suzuki-Miyaura coupling. The method has also been demonstrated to be applicable to silicon nucleophiles, leading to the formation of Lewis acidity-diminished stable silyl-B(dan) and -B(aam) in one pot.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Engineering, Environmental
Qiuju Li, Xueyu Wang, Lianjun Song, Lanlan He, Qiao Yu, Xiao Xiao, Songdong Ding
Summary: In this study, it was found that by introducing cyclohexyl substituent to the DGA ligand skeleton, the extractability of Sr2+ in HNO3 solution could be significantly enhanced, and the effect is more significant with more cyclohexyl substituents.
JOURNAL OF ENVIRONMENTAL CHEMICAL ENGINEERING
(2023)
Article
Multidisciplinary Sciences
Najmedin Azizi, Mostafa Saadat, Mahtab Edrisi
Summary: A novel composite FeCeOx@g-C3N4 was developed in this study, which exhibited remarkable catalytic activity and recyclability, enabling the implementation of green chemistry principles in one-pot reactions.
SCIENTIFIC REPORTS
(2023)
Article
Chemistry, Applied
Nathan Trometer, Matthieu Roignant, Elisabeth Davioud-Charvet
Summary: Here, we report a safe and economical multigram synthesis of 6-fluoromenadione, which is an important intermediate in the synthesis of novel biologically active agents.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2022)
Article
Chemistry, Physical
Zahra Sadeghi, Zohreh Mirjafary, Gholamreza Najafi, Fatameh Heidari, Hoda Abolhasani
Summary: Novel 5-substituted tetrazole derivatives containing the sulfonamide group were synthesized successfully using an azide-nitrile cycloaddition reaction. This synthetic protocol offers a valuable tool for the synthesis of functionalized tetrazole derivatives due to the easy availability of inexpensive starting materials, avoidance of hazardous organic azide, and mild reaction conditions. The structures of the synthesized compounds were confirmed using FT-IR, 1HNMR, and 13CNMR analysis. Additionally, molecular docking and ADMET studies revealed the potential drug-likeness of the synthesized molecules, with some showing promising characteristics. The antifungal activity of one compound (5c) against pathogenic fungi strains was also investigated.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Article
Chemistry, Multidisciplinary
Min Ye, Fan Xu, Yun Bai, Fanglian Zhang, Wenjia Wang, Yiping Qian, Zhengwang Chen
Summary: A convenient and efficient annulation reaction method has been developed for the synthesis of dinitrile-substituted cyclopropanes. The method exhibits broad substrate compatibility and high yields, achieved through tandem Michael-type addition and intramolecular cyclization.
Article
Chemistry, Multidisciplinary
Feng Jiang, Feng Zhao, Youliang He, Xiantao Luo, Xiaoming Wang
Summary: A new method combining iridium catalysis and photochemical organocatalysis has been developed to convert amides into beta-substituted tertiary alkylamines, with high yields and a wide substrate scope.
CELL REPORTS PHYSICAL SCIENCE
(2022)
Article
Chemistry, Multidisciplinary
Feng Jiang, Feng Zhao, Youliang He, Xiantao Luo, Xiaoming Wang
Summary: In this study, a combination of iridium catalysis and photochemical organocatalysis was developed for the deoxygenative conversion of amides to beta-substituted tertiary alkylamines with moderate to excellent yields (up to 93%) and broad substrate scope (57 examples).Mechanistic studies suggest that the interaction of iridium-catalyzed partial reduction of amides and photochemical organocatalysis of alpha-bromoketones under visible light is crucial for this cross-coupling process. The active electrophilic radicals from photochemical organocatalysis act as functionalization partners with the in-situ-formed enamine intermediates from the Ir-catalyzed reduction of amides, leading to the formation of beta-substituted amines.
CELL REPORTS PHYSICAL SCIENCE
(2022)
Article
Chemistry, Organic
Haojie Ma, Zhou Sun, Jinlei Liu, Xia Zhang, Huali Cui, Yuqi Zhang, Jijiang Wang
Summary: The synthesis of N-acylpyrazoles was achieved in high yields through intermolecular cyclization of benzohydrazide and pentane-2,4-dione mediated by CBr4. This method offers advantages such as mild conditions, environmental friendliness, ease of operation, and step economy, making it a useful strategy for synthesizing biologically active molecules.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Guangde Jiang, Chunshuai Huang, Wesley Harrison, Hongxiang Li, Megan Zhou, Huimin Zhao
Summary: We report the efficient synthesis of bridged bicyclic nitrogen heterocycles using ene reductases (EREDs) and iridium photocatalysis. The reaction requires oxygen and produces oxidized flavin, allowing selective dehydrogenation of cyclohexanone derivatives and subsequent intramolecular aza-Michael addition. The resulting compounds have potential applications in drug discovery.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Poosa Mallesham, Venkatesh Miriyala, Satyanarayana Yennam, Paul Douglas Sanasi, Manoranjan Behera
Summary: An efficient method for synthesizing substituted 2-amino phenoxazinones using T3P & REG via oxidative cross-coupling of commercially available 2-amino phenols is described. The reaction is transition metal-free, enzyme-free, and non-photochemical, leading to shorter reaction times and moderate to good yields.
Article
Biochemistry & Molecular Biology
Xiangli Gao, Huan Liu, Jianbo Shuai, Junmeng Zhao, Guowen Zhou, Quanbo Huang, Hao Ling, Wenjiao Ge, Xiaohui Wang
Summary: A novel ionic liquid, [DBUC8]Cl, was synthesized and found to have stronger alkalinity than other imidazolyl ionic liquids, enabling more efficient dissolution of cellulose. Highly substituted cellulose acetate (CA) was successfully synthesized under mild conditions without the use of a catalyst, and a transparent cellulose acetate film (CAF) was obtained. The new DBU-derived ionic liquid offers a versatile platform for sustainable and efficient production of cellulose-derived bioplastics.
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
(2023)
Article
Engineering, Mechanical
Lucas Grilli, Fabrice Casset, Christine Bressy, Hugues Brisset, Jean-Francois Briand, Raphaelle Barry-Martinet, Mikael Colin
Summary: This paper presents the development and experimentation of transparent vibrating piezoelectric micromembranes for protecting immersed measurement instruments from marine biofouling. Laboratory bioassays showed great potential against bacterial adhesion, while in situ tests confirmed their antifouling effect. However, in situ experimentations revealed issues with the piezo driver actuating the vibrating membranes, indicating a need for further improvements.
Review
Chemistry, Analytical
Alexandre Sala, Hugues Brisset, Andre Margaillan, Jean-Ulrich Mullot, Catherine Branger
Summary: This article provides an overview of the current state of research on electrochemical sensors based on ion-imprinted polymers (IIPECS) for quantifying metal ions. The potential of IIPECS in quantifying metal ions with high sensitivity and selectivity is demonstrated through numerous application examples.
TRAC-TRENDS IN ANALYTICAL CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Nesrine Shaiek, Hassan Denawi, Mathieu Koudia, Roland Hayn, Steffen Schafer, Isabelle Berbezier, Chokri Lamine, Olivier Siri, Abdelwaheb Akremi, Mathieu Abel
Summary: The on-surface synthesis of metal-organic covalent coordination networks with a dense Kagome lattice of metallic centers is reported. The charge states and magnetic properties of Cu and Mn in this structure are investigated, and the influence of charge transfer on the structural properties is analyzed. In addition, the magnetic couplings and properties of the structure are predicted, which has potential applications for realizing the quantum anomalous Hall effect.
ADVANCED MATERIALS INTERFACES
(2022)
Article
Nanoscience & Nanotechnology
Tina Skorjanc, Dinesh Shetty, Felipe Gandara, Simon Pascal, Nawavi Naleem, Salma Abubakar, Liaqat Ali, Abdul Khayum Mohammed, Jesus Raya, Serdal Kirmizialtin, Olivier Siri, Ali Trabolsi
Summary: A highly substituted cationic azacalix[4]arene-based covalent organic framework (ACA-COF) was synthesized using microwave irradiation and the Zincke reaction, which constrained its conformational flexibility and produced an ordered material. The ACA-COF showed rapid adsorption rates for uric acid and creatinine, indicating its potential in addressing water scarcity in arid areas.
ACS APPLIED MATERIALS & INTERFACES
(2022)
Article
Chemistry, Applied
Tereza Horackova, Manon H. E. Bousquet, Adrien Morice, Ugo Triballier, Gabriel Canard, Pavel Lhotak, Denis Jacquemin, Simon Pascal, Olivier Siri
Summary: This study reports that the substitution of nitro-containing electron-withdrawing groups by weaker nitrile ones promotes the formation of zwitterionic tautomer of DABQDI in apolar solvents. The absence of intramolecular hydrogen bonding between the nitrile aromatic N-substituent and the N-H proton of the bridge in the canonical form is rationalized using theoretical calculations, leading to the fully zwitterionic electronic structure of the nitrile-containing DABQDI.
Article
Materials Science, Multidisciplinary
Hassan Denawi, Mathieu Abel, Abdelkader Boukortt, Olivier Siri, Roland Hayn
Summary: We predict two switchable one-dimensional spin-polarized semiconductors based on metal-organic coordination chains. These coordination chains can transition between semiconductor and half-metal or between small and large energy gap semiconductors when oxidized by chlorine. They have reversible electronic and magnetic characteristics and show promise as multi-functional switches in nanoelectronics and spintronics.
JOURNAL OF MAGNETISM AND MAGNETIC MATERIALS
(2022)
Article
Biochemistry & Molecular Biology
Elora Vedie, Raphaelle Barry-Martinet, Vincent Senez, Mattias Berglin, Patrik Stenlund, Hugues Brisset, Christine Bressy, Jean-Francois Briand
Summary: This article examines the influence of surface characteristics and seawater parameters on the settlement of marine micro- and macroorganisms. It is found that mechanical properties and non-evolutive wettability do not have a major impact on biofouling abundance and diversity, while evolutive wetting properties can strongly reduce macrofouler colonization.
MACROMOLECULAR BIOSCIENCE
(2022)
Article
Nanoscience & Nanotechnology
Muhammad Awais Aslam, Tuan Hoang Tran, Antonio Supina, Olivier Siri, Vincent Meunier, Kenji Watanabe, Takashi Taniguchi, Marko Kralj, Christian Teichert, Evgeniya Sheremet, Raul D. Rodriguez, Aleksandar Matkovic
Summary: This study proposes a universal approach to synthesize high-quality networks of nanoribbons from different 2D materials and demonstrates their wide applicability. By controlling the crystallographic direction of the nanoribbon edges and decorating them with plasmonic particles, excellent electrical characteristics and potential applications in opto-electronic devices can be achieved.
NPJ 2D MATERIALS AND APPLICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Amine Kriat, Simon Pascal, Brice Kauffmann, Yann Ferrand, David Berge-Lefranc, Didier Gigmes, Olivier Siri, Anthony Kermagoret, David Bardelang
Summary: The binding modes of CB[7] to Viologen-Phenylene-Imidazole (VPI) guest were investigated by NMR, ITC, X-ray diffraction, UV-vis and fluorescence spectroscopies after adding hydrophobic groups on the two extremities of VPI. The results showed that CB[7] preferred to bind to the extended imidazole station (VPI-N) similar to the previously observed binding modes. However, when the viologen was extended by a tolyl group (T-VPI), CB[7] shuttled between the T and P stations at acid pH or after Ag+ addition. The CB[7]·T-VPI complex exhibited a metal-actuated thermodynamic stop-and-go molecular shuttle behavior controlled by Ag+ concentration.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Electrochemistry
Jean-Francois Longevial, Iryna Knysh, Shaymaa Al Shehimy, Lhoussain Khrouz, Aramugam Pandurangan, Simon Pascal, Gabriel Canard, Christophe Bucher, Denis Jacquemin, Olivier Siri
Summary: Researchers have synthesized and characterized the soluble 6,13-dipivaloyl-5,14-dihydro-5,7,12,14-tetraazapentacene and its aromatic counterpart. Using complementary chemical, (spectro)-electrochemical, theoretical, and spectroscopic techniques, all the intermediates generated during the electrochemical processes of these compounds were fully characterized. The results demonstrate the ambipolar redox behavior of 6,13-dipivaloyl-5,14-dihydro-5,7,12,14-tetraazapentacene, leading to drastic color changes through proton-coupled electron transfer in a totally reversible fashion.
ELECTROCHIMICA ACTA
(2023)
Article
Chemistry, Organic
Tatiana Munteanu, Valeirie Mazan, Mourad Elhabiri, Camil Benbouziyane, Gabriel Canard, Denis Jacquemin, Olivier Siri, Simon Pascal
Summary: The formation of N- or C-substituted dinitro-tetraamino-phenazines (P1-P5) is made possible through the oxidative condition by forming two intermolecular C-N bonds from 5-nitrobenzene-1,2,4-triamine precursors. The photophysical studies demonstrate that these compounds have green absorbing and orange-red emitting dyes with enhanced fluorescence in the solid state. Further reduction of the nitro functions leads to the isolation of a benzoquinonediimine-fused quinoxaline (P6), which can undergo diprotonation to form a dicationic coupled trimethine dye absorbing beyond 800 nm.
Article
Chemistry, Multidisciplinary
Christine Elian, Benjamin Mourot, Camil Benbouziyane, Jean-Pierre Malval, Sonia Lajnef, Fabienne Peyrot, Florian Massuyeau, Olivier Siri, Denis Jacquemin, Simon Pascal, Davy-Louis Versace
Summary: In this study, a near-infrared-absorbing heptamethine compound incorporating bulky benzo[cd]indole heterocycles was designed to prevent self-aggregation of the dye. Compared to a reference system, the incorporation of the heterocycles resulted in a significantly enhanced photoinitiating reactivity. The researchers achieved a 100% conversion of acrylates C=C bonds even under air conditions by incorporating the near-infrared sensitizer into a three-component system, which allowed for self-regeneration of the photoredox cycle. This cycle was thoroughly investigated by identifying the intermediates using EPR spectroscopy.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Ilan Boulet, Simon Pascal, Frederic Bedu, Igor Ozerov, Alain Ranguis, Thomas Leoni, Conrad Becker, Laurence Masson, Aleksandar Matkovic, Christian Teichert, Olivier Siri, Claudio Attaccalite, Jean-Roch Huntzinger, Matthieu Paillet, Ahmed Zahab, Romain Parret
Summary: Hybrid van der Waals heterostructures consisting of 2D materials and organic molecules show potential for efficient devices. This study focuses on a quinoidal zwitterion/MoS2 hybrid system where organic crystals grow on the MoS2 surface and rearrange after thermal annealing. The charge transfer between the zwitterions and MoS2 depends on the molecular film conformation, but the transistor performance remains unaffected. Additionally, MoS2 transistors can accurately detect structural modifications during organic layer phase transitions, making them valuable tools for on-chip detection of molecular events.
NANOSCALE ADVANCES
(2023)
Article
Chemistry, Physical
Anthony Thomas, Thomas Leoni, Olivier Siri, Conrad Becker, Martin Unzog, Christian Kern, Peter Puschnig, Peter Zeppenfeld
Summary: We report the formation of a high-order commensurate (HOC) structure of 5,14-dihydro-5,7,12,14-tetraazapentacene (DHTAP) molecules on a highly corrugated Cu(110)-(2 x 1)O surface. Scanning tunneling microscopy reveals that the DHTAP molecules exhibit a periodic uniaxial arrangement, with groups of seven molecules distributed over nine substrate lattice spacings along the [110] direction. DFT calculations indicate that this peculiar arrangement is due to the different tilting of the seven DHTAP molecules within the quasi one-dimensional HOC unit cell.
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
(2022)
Article
Chemistry, Multidisciplinary
Paul-Gabriel Julliard, Simon Pascal, Olivier Siri, Diego Cortes-Arriagada, Luis Sanhueza, Gabriel Canard
Summary: Starting from pyrrole-carbinol derivatives, a set of three optimized experimental conditions was used to prepare six dipyrromethanes (DPM) bearing meso-poly-halogeno-alkyl chains. The synthesis of expected porphyrins was achieved through different methods, with the competitive straightforward formation of bis-formyl porphyrins. The electron-withdrawing character of various substituents on porphyrins was studied through a combination of different techniques.
COMPTES RENDUS CHIMIE
(2021)
