Article
Chemistry, Multidisciplinary
Borja Cirera, Alexander Riss, Pingo Mutombo, Jose Urgel, Jose Santos, Marco Di Giovannantonio, Roland Widmer, Samuel Stolz, Qiang Sun, Max Bommert, Roman Fasel, Pavel Jelinek, Willi Auwarter, Nazario Martin, David Ecija
Summary: The design of organometallic complexes is crucial in modern organic chemistry and catalysis. On-surface synthesis has recently emerged as a disruptive method to design compounds and nanomaterials previously considered impossible. The activation of inner diacetylene moieties of a molecular precursor by copper surface adatoms has led to the formation of unprecedented organocopper metallacycles on Cu(111), paving the way for new avenues in organometallic compound engineering and polyyne chemistry on surfaces.
Correction
Chemistry, Inorganic & Nuclear
Firdaus Rahaman Gayen, Abdul Aziz Ali, Debashree Bora, Saptarshi Roy, Supriya Saha, Lakshi Saikia, Rajib Lochan Goswamee, Biswajit Saha
Summary: This study focuses on the synthesis and characterization of a ferrocene functionalized Schiff base containing Cu(II) complex, and demonstrates its catalytic activity in the azide alkyne cycloaddition reaction at parts-per-million levels.
DALTON TRANSACTIONS
(2021)
Article
Chemistry, Organic
Robby Vroemans, Sergio R. Ribone, Joice Thomas, Luc Van Meervelt, Thierry Ollevier, Wim Dehaen
Summary: A new method for preparing novel homochiral atropisomeric sulfanyl- and sulfoxide-substituted naphthyltriazoles is described in this study, providing a new pathway for stable 1,2,3-triazole-based atropisomers. Sixteen sulfanyl-substituted naphthyltriazoles were obtained via triazolization reaction, followed by monooxidation. The absolute configuration of the substituted naphthyltriazoles was determined using X-ray crystallography and confirmed with computational DFT calculations.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Review
Chemistry, Physical
Chang-Qing Qin, Cheng Zhao, Guo-Shu Chen, Yun-Lin Liu
Summary: Catalytic enantioselective azide-alkyne cycloaddition (E-AAC) is an efficient technology for constructing diverse chiral triazoles, with applications in synthetic and medicinal chemistry, biological chemistry, and materials science. Significant developments have been made in copper-, nickel-, iridium-, and rhodium-catalyzed E-AAC reactions in the past six years. This review summarizes these advancements according to different strategies implemented.
Article
Chemistry, Organic
Carl T. Bormann, Christeena Mathew, Margarida M. Antonio, Aude Trotti, Farzaneh Fadaei-Tirani, Kay Severin
Summary: In this study, the synthesis of a terminal 1-alkynyl triazene is described, and subsequent functionalization expands the structural diversity of this compound class. Furthermore, its applications in the synthesis of di- and triynes, as well as in the preparation of (hetero)aromatic triazenes through metal-catalyzed cyclization reactions, are explored.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Xiai Luo, Yu Zhao, Susu Tao, Zhong-Tao Yang, Hui Luo, Weiguang Yang
Summary: A simple synthesis method for (Z)-1,2-dihydro-2-iminoquinolines has been achieved using copper-catalyzed reaction of 1-(2-aminophenyl)ethan-1-ones, sulfonyl azides, and terminal ynones under mild conditions. The Z-configured products are obtained through a base-free CuAAC/ring-opening process due to hydrogen bonding.
Article
Chemistry, Multidisciplinary
Fei-Fei Wang, Jia-Hui Li, Hai-Yan Liu, Shu-Ping Deng, Ying-Ying Liu, Jian-Fang Ma
Summary: Three distinctive coordination polymers were solvothermally synthesized using a resorcin[4]arene ligand. Among them, compound 1 showed efficient and selective catalytic performance, and could be recycled with preservation of its catalytic capability and structural integrity.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Suguru Yoshida, Yuki Sakata, Yoshihiro Misawa, Takamoto Morita, Tomoko Kuribara, Harumi Ito, Yuka Koike, Isao Kii, Takamitsu Hosoya
Summary: Efficient consecutive formation of 1,2,3-triazoles using multiazide platforms has been achieved in this study. A four-step synthesis of tetrakis(triazoles) was successfully performed from a tetraazide platform molecule, based on the unique clickability of the 1-adamantyl azido group. This method was applied to the convergent synthesis of tetrafunctionalized probes in a modular synthetic manner.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Samuel Pearce, Juan Perez-Mercader
Summary: By integrating various chemical processes, simplification of PISA process and routes to complexity and adaptation in chemical systems can be achieved.
ACS CENTRAL SCIENCE
(2021)
Article
Chemistry, Multidisciplinary
Gargi Chakraborti, Tirtha Mandal, Charles Patriot Roy, Jyotirmayee Dash
Summary: A cascade sequence involving [3+2] cycloaddition, 1,2-acyl migration and hydrolysis produces 2H-1,2,3-triazoles with regioselectivity, using a CuI-prolinamide catalyst system in aqueous media. Prolinamide promotes novel organocatalytic 1,2-acyl migration and hydrolysis of N-2-carboxyalkylated triazoles in the reaction.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Inorganic & Nuclear
Lan Qin, Ran Ren, Xiaoxue Huang, Xinyi Xu, Hao Shi, Ranran Huai, Nuan Song, Lu Yang, Suna Wang, Daopeng Zhang, Zhen Zhou
Summary: The organic-inorganic hybrid Anderson-type polyoxometalate (POM 1) was synthesized, which showed enhanced luminescence property and photocatalytic activity. The catalyst exhibited excellent selective degradation ability towards a positive-charged methylene blue dye and the in-situ reduction of Cu(II) ions to Cu(I) ions via photoinduced electron transfer resulted in enhanced heterogeneous catalytic performance.
JOURNAL OF SOLID STATE CHEMISTRY
(2022)
Article
Polymer Science
Han Byul Song, Nancy Sowan, Austin Baranek, Jasmine Sinha, Wayne D. Cook, Christopher N. Bowman
Summary: The present study utilized photoinitiated copper-catalyzed azide-alkyne cycloaddition (CuAAC) polymerization to create structurally diverse glassy polymer networks. By systematically altering the monomer backbone rigidity and the reactive functional group density, networks with varied mechanical properties and strengths were obtained. Incorporating flexible monomers and changing the reactive end groups resulted in improvements in elongation at break and tensile toughness in the polymer networks.
Article
Chemistry, Inorganic & Nuclear
Atousa Khanzadeh, Saeed Ataie, R. Tom Baker
Summary: Two tetranuclear Cu(I) complexes with thiolate- and amido-SNS ligands were characterized, and their reactivities in the copper-catalyzed azide-alkyne cycloaddition reaction were studied. The amido ligand undergoes irreversible N-protonation, while the thiolate complex shows good activity and high yields under base-free conditions in water at 70°C. DFT calculations indicate the proton-shuttle role of thiolate donor in the formation of the initial dicopper σ,π-alkynyl intermediate.
DALTON TRANSACTIONS
(2023)
Article
Chemistry, Medicinal
Ryosuke Kori, Keigo Murakami, Yoshitake Nishiyama, Tatsuya Toma, Satoshi Yokoshima
Summary: The study reveals the mechanism of copper-mediated reaction for the formation of nitriles, involving iodoalkyne and iodotriazole as intermediates.
CHEMICAL & PHARMACEUTICAL BULLETIN
(2021)
Article
Chemistry, Applied
Jie Wu, R. Hunter Cooke III, Harrison A. Livingston, Grace L. Parker, Bayley C. Peoples, Alan Ekin, Robson F. Storey
Summary: The study focused on creating alternative crosslinking polyurethanes (ACPU), where different glycol ether plasticizers were used to reduce the viscosity of poly(alkynyl carbamate) without sacrificing its alkyne functionality. The addition of these plasticizers resulted in softer coatings with lower glass transition temperatures compared to traditional controls. The solvent resistance of the modified coatings was generally comparable to controls, except for those created using DEGBE and DEGMEE at a specific loading level.
PROGRESS IN ORGANIC COATINGS
(2021)
Editorial Material
Chemistry, Multidisciplinary
Ottavia Bettucci, Jorge Pascual, Silver-Hamill Turren-Cruz, Andrea Cabrera-Espinoza, Wakana Matsuda, Sebastian F. Voelker, Hans Koebler, Iwona Nierengarten, Gianna Reginato, Silvia Collavini, Shu Seki, Jean-Francois Nierengarten, Antonio Abate, Juan Luis Delgado
Summary: Multi-branched molecules based on pillar[5]arene have shown promising performance as hole-transporting materials in perovskite solar cells. The dendrimer-like compounds derived from extended triarylamine dendrons exhibit improved hole transporting properties from the first to the second generation. Furthermore, economic analysis indicates that the pillar[5]arene-based material is more cost-effective compared to the reference material.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Ottavia Bettucci, Jorge Pascual, Silver-Hamill Turren-Cruz, Andrea Cabrera-Espinoza, Wakana Matsuda, Sebastian F. Voelker, Hans Koebler, Iwona Nierengarten, Gianna Reginato, Silvia Collavini, Shu Seki, Jean-Francois Nierengarten, Antonio Abate, Juan Luis Delgado
Summary: Recently, it has been shown that grafting extended triarylamine onto a pillar[5]arene core to generate dendrimer-like compounds can be used as hole-transporting materials in perovskite solar cells. The positive dendritic effect was evident in the improvement of hole transporting properties from the first to the second-generation compound.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Marine Remy, Iwona Nierengarten, Boram Park, Michel Holler, Uwe Hahn, Jean-Francois Nierengarten
Summary: By combining pillar[5]arene-containing [2]rotaxane building blocks with pentafluorophenyl ester functions, stopper exchange reactions can be carried out to generate a variety of [2]rotaxanes with different stoppers. This new strategy provides easy access to a photoactive [2]rotaxane containing a C-60 moiety and two Bodipy stoppers starting from a fullerene-functionalized pillar[5]arene derivative.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Review
Biochemistry & Molecular Biology
Iwona Nierengarten, Michel Holler, Marine Remy, Uwe Hahn, Aurelien Billot, Robert Deschenaux, Jean-Francois Nierengarten
Summary: Pillar[5]arenes with ten peripheral substituents are attractive scaffolds for constructing nanomaterials with controlled functional groups distribution. This review focuses on functionalizing pillar[5]arene derivatives with small dendrons to create dendrimer-like nanomaterials and bioactive compounds, such as non-viral gene vectors, bioactive glycoclusters, and liquid-crystalline materials.
Article
Chemistry, Inorganic & Nuclear
Brigino Ralahy, Uwe Hahn, Emeric Wasielewski, Jean-Francois Nierengarten
Summary: Phenanthroline ligands with different substituents were synthesized to prepare corresponding copper(I) complexes. While biphenyl-substituted ligands can form homoleptic copper(I) complexes, tetraarylbenzene-substituted ligands cannot. The obtained copper(I) complexes exhibit dynamic conformational exchange in solution.
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Thi Minh Nguyet Trinh, Franck Schillinger, Sebastiano Guerra, Eric Meichsner, Iwona Nierengarten, Uwe Hahn, Michel Holler, Jean-Francois Nierengarten
Summary: A series of macrocyclic bis-malonates with different spacer units were used for regioselective functionalization of fullerene. By systematically modifying the spacers, fullerene bis-adducts with varied addition patterns were obtained. Finally, the bridging silylene groups were cleaved to yield acyclic fullerene bis-adducts with four alcohol functions.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Iwona Nierengarten, Uwe Hahn, Michel Holler, Beatrice Delavaux-Nicot, Emmanuel Maisonhaute, Nierengarten Jean-Francois
Summary: Our research program focuses on the development of molecular and supramolecular systems using pillar[5]arene and porphyrins. We have successfully created giant molecular machines and light-harvesting devices by functionalizing the pillar[5]arene scaffold with metalloporphyrins. Additionally, we have utilized the host-guest properties of pillar[5]arene derivatives to prepare photoactive mechanically interlocked molecules, which exhibit efficient inter-component photo-induced energy transfer processes.
JOURNAL OF PORPHYRINS AND PHTHALOCYANINES
(2023)
Article
Chemistry, Multidisciplinary
Franck Schillinger, Uwe Hahn, Sebastiano Guerra, Thi Minh Nguyet Trinh, David Sigwalt, Michel Holler, Iwona Nierengarten, Jean-Francois Nierengarten
Summary: Bis- and tris-malonates were synthesized by reacting malonate derivatives with alcohol groups with di-tert-butylsilyl bis(trifluoromethanesulfonate) and tert-butyl(trichloro)silane, respectively. These compounds were used for regioselective bis- and tris-functionalization of C-60 under Bingel conditions. By optimizing the malonate precursors with different linkers between the central Si atom and the malonate groups, specific bis- and tris-adducts with excellent regioselectivity were obtained. A complete understanding of the factors governing the regioselectivity was achieved through computational studies and analysis of the by-products. Desilylation reactions of the resulting fullerene adducts yielded acyclic fullerene adducts with alcohol functions.
HELVETICA CHIMICA ACTA
(2023)
Biographical-Item
Chemistry, Multidisciplinary
Jean-Francois Nierengarten, Jean-Marie Lehn
HELVETICA CHIMICA ACTA
(2023)
Article
Chemistry, Multidisciplinary
Maksym Dekhtiarenko, Gabriel Mengheres, Eric Levillain, Zoia Voitenko, Iwona Nierengarten, Jean-Francois Nierengarten, Sebastien Goeb, Marc Salle
Summary: Pillar[5]arene derivatives with peripheral TTF subunits were efficiently synthesized using a decabrominated pillar[5]arene building block and appropriate TTF-thiolate nucleophiles. A fully substituted pillar[5]arene exTTTF conjugate was prepared from a clickable pillar[5]arene derivative and an exTTF derivative with a terminal alkyne function. Electrochemistry studies showed significant electronic interactions between the TTF subunits in the conjugates, while no interactions were detected in the exTTF-containing system. Binding studies demonstrated the capability of all the conjugates to form host-guest complexes with 1,6-dicyanohexane and a methanofullerene bearing a cyanoalkane moiety.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Pauline Pieper, Yassine Chadi, Iwona Nierengarten, Uwe Hahn, Eric Meichsner, Thi Le Anh Nguyen, Joaquin Barbera, Robert Deschenaux, Jean-Francois Nierengarten
Summary: In this study, liquid-crystalline mechanically interlocked molecules were synthesized using a click strategy, and the liquid-crystalline properties of different numbers of peripheral cyanobiphenyl units were investigated.
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
