Article
Chemistry, Multidisciplinary
Cristina Naranjo, Azahara Doncel-Gimenez, Rafael Gomez, Juan Arago, Enrique Orti, Luis Sanchez
Summary: The synthesis and self-assembling features of N-annulated perylene diimide (NPBI) 1 in different solvents are reported. Compound 1 possesses two chiral linkers derived from (S)-(+)-alaninol, connecting the central aromatic NPBI segment and the peripheral trialkoxybenzamide units. It has been demonstrated that NPBI 1 shows a strong tendency to self-assemble even in a good solvent like CHCl3, forming chiral dimers driven by the p-stacking of two units of the NPBI core.
Article
Chemistry, Physical
Andrea Santilli, Andrea Lapi, Jacopo Cautela, Marco D'Abramo, Cheng Giuseppe Chen, Alessandra Del Giudice, Simona Sennato, Domagoj Belic, Victor Hugo Soto Tellini, Karin Schillen, Maria Chiara di Gregorio, Luciano Galantini
Summary: The molecular design in this work enables the encoding of multiple desirable features (such as bio-origin, temperature resistance, and chirality of the aggregates) in the same light-responsive system, which has never been reported before for a single molecule. This combination of properties could be relevant for the development of robust, stimuli-responsive bio-vectors.
JOURNAL OF COLLOID AND INTERFACE SCIENCE
(2022)
Article
Chemistry, Multidisciplinary
Motoki Tsuchiya, Ryo Inoue, Kentaro Tanaka, Yasuhiro Morisaki
Summary: Planar chiral [2.2]paracyclophane was used as a chiral scaffold to induce twist chirality in the anthracene moiety, resulting in chiroptical properties such as circular dichroism and circularly polarized luminescence. The experimental results were well reproduced by theoretical studies, which also revealed the origin of these properties.
CHEMISTRY-AN ASIAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Sylwia Parzyszek, Jacopo Tessarolo, Adrian Pedrazo-Tardaos, Ana M. Ortuno, Maciej Baginski, Sara Bals, Guido H. Clever, Wiktor Lewandowski
Summary: This study proposes a strategy to achieve strongly dissymetric CPL in nanocomposite films based on chiroptical induction and energy transfer to semiconductor nanocrystals. By controlling the chirality of helical nanofilaments in liquid crystal matrix and adjusting energy transfer from organic films to quantum dots, CPL wavelengths can be conveniently tuned. This approach provides a simple and versatile method to modulate the CPL activity of organic materials.
Article
Chemistry, Multidisciplinary
Slav A. Semerdzhiev, Ine Segers-Nolten, Paul van der Schoot, Christian Blum, Mireille M. A. E. Claessens
Summary: The presence of alpha-synuclein fibrils in brain cells is a characteristic of several alpha-synucleinopathies. Recent research shows that the N-protein of SARS-CoV-2 can accelerate the aggregation of alpha-synuclein, leading to the formation of mixed fibrils and eventually pure alpha-synuclein fibril strain. This strain transformation may be related to the cell-to-cell spread of the pathology and disease onset.
Review
Chemistry, Multidisciplinary
Kenichi Kato, Shixin Fa, Tomoki Ogoshi
Summary: Pillar[n]arenes, composed of benzene panels with para-methylene linkages, are symmetrical macrocyclic compounds. The planar chirality of each panel and its preference for chirality-aligned states make pillar[n]arenes attractive scaffolds for chiroptical materials with intense circular dichroism (CD) signals. Additionally, the dynamic nature of the chirality in pillar[n]arenes allows for time- and procedure-dependent alignment phenomena and response to chiral guests, providing molecular sensors.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Shixin Fa, Keisuke Adachi, Yuuya Nagata, Kouichi Egami, Kenichi Kato, Tomoki Ogoshi
Summary: Regulating the chirality of macrocyclic host molecules and supramolecular assemblies is crucial for governing their properties, and pre-regulation of building blocks' chirality in pillar[5]arene-based chiral nanotube formation has been shown to be more efficient than post-regulation strategies.
Article
Chemistry, Multidisciplinary
Fan Xu, Lukas Pfeifer, Stefano Crespi, Franco King-Chi Leung, Marc C. A. Stuart, Sander J. Wezenberg, Ben L. Feringa
Summary: The study focused on controlling supramolecular polymerization using photoresponsive stiff-stilbene-based bis-urea monomers in organic solvents, achieving fast light-triggered depolymerization-polymerization and reversible gel formation. Precise control over supramolecular polymerization and gelation was achieved by manipulating the high photostationary states of cis-trans isomerization. The research also revealed a kinetically controlled nucleation-elongation mechanism for temperature-dependent and photoinduced supramolecular polymerization in organic solvents.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Physical
Yu-Qing Bai, Xin-Wei Wang, Bo Wu, Xiao-Qing Wang, Rong-Zheng Liao, Man Li, Yong-Gui Zhou
Summary: The development of chiral ligands for precise stereocontrol is essential in asymmetric catalysis. However, the utilization of chiral oxazole-pyridine-type ligands has been limited compared to established chiral pyridine-pyridine and pyridine-oxazoline-type ligands. In this study, a new class of planar-chiral oxazole-pyridine N,N-ligands based on [2.2]paracyclophane was designed and synthesized. These ligands exhibited excellent performance in the enantioselective palladium-catalyzed acetoxylative cyclization, providing chiral cis-hydrobenzofurans with potent NF-κB inhibition, thereby demonstrating the promising potential of chiral oxazole-pyridine ligands as an efficient N,N-ligand scaffold.
Article
Chemistry, Multidisciplinary
Raviraj Ananda Thorat, Yogesh Mandhar, Devendra Parganiha, Khushbu Bindesh Patil, Vikram Singh, Batul Shakir, Saravanan Raju, Sangit Kumar
Summary: The reaction of chiral 2-iodoferrocenecarboxamide, palladium(II) acetate, and triphenylphosphine ligand in acetonitrile resulted in the formation of an air-stable chiral (S-p)-2-(N,N-diisopropyl ferrocenecarboxamide) triphenylphosphine palladium(II) iodide complex. The isolated chiral palladium complex was characterized by various spectroscopic techniques and X-ray crystallography, revealing its structural and electronic properties. Furthermore, the synthesized chiral palladium complex exhibited catalytic activity in Suzuki-Miyaura coupling, Tsuji-Trost coupling, and phosphonation reactions.
Article
Spectroscopy
Giuseppe Mazzeo, Sonia Pedotti, Giovanna Longhi, Angela Patti, Sergio Abbate
Summary: This study investigated the spectroscopic and chiroptical properties of single enantiomers of three 1,2-substituted ferrocene derivatives, confirming the previously assigned absolute configurations through comparison of experimental and DFT calculated data.
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY
(2022)
Article
Optics
An'an Wu, Yoshito Y. Tanaka, Tsutomu Shimura
Summary: Chiral plasmonic structures have drawn attention due to their significant chiroptical response, with the interaction between constituents playing a crucial role. Plasmon coupling and hybridization techniques enhance the chiroptical response, while sensitivity to structure configuration allows precise control through adjusting gap size and twisted angle, providing insights for future design and improvement in metamaterial applications.
Article
Chemistry, Multidisciplinary
Pengfei Wu, Adriana Pietropaolo, Mariagrazia Fortino, Shuhei Shimoda, Katsuhiro Maeda, Tatsuya Nishimura, Masayoshi Bando, Naofumi Naga, Tamaki Nakano
Summary: An unprecedented non-uniform self-folding phenomenon of artificial polymer chains has been achieved through the design of specific molecular structures. The folded structure is formed and stabilized in the solid state, resulting in remarkably enhanced chiroptical properties. Experimental and theoretical analyses have provided explanations for this phenomenon. Further evaluation of the polymer arrangements in the solid state has been conducted through transmission electron microscopic observations and molecular dynamics simulations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Multidisciplinary Sciences
Shixin Fa, Tan-hao Shi, Suzu Akama, Keisuke Adachi, Keisuke Wada, Seigo Tanaka, Naoki Oyama, Kenichi Kato, Shunsuke Ohtani, Yuuya Nagata, Shigehisa Akine, Tomoki Ogoshi
Summary: This study demonstrates real-time monitoring of the chirality transfer process and presents an assembly method for achieving diastereomerically pure structures from a statistically random distribution. By utilizing the synergistic effect of ion pairing, the chirality transfer is achieved through the flipping of molecular units, leading to the construction of diastereomerically pure trimers.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Diana P. N. Goncalves, Torsten Hegmann
Summary: The majority of nanomaterials transfer or amplify chirality through surface installation of chiral ligands, but surface-modified cellulose nanocrystals with core chirality show the ability to quantify transmission and amplification of core chirality through space in a liquid crystal medium. Functionalized CNCs with achiral molecules have better solubility in the liquid crystal matrix, serving as efficient chiral inducers, while functionalization with chiral molecules only marginally increases helical distortion efficacy, indicating the high propensity of CNCs to transfer chirality from an inherently chiral core.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Manuel A. Martinez, Azahara Doncel-Gimenez, Jesus Cerda, Joaquin Calbo, Rafael Rodriguez, Juan Arago, Jeanne Crassous, Enrique Orti, Luis Sanchez
Summary: The study explores the self-assembling features of two series of N-annulated perylene bisimides, highlighting the significant influence of the distance between the PBI core and the peripheral groups on chiroptical properties and supramolecular polymerization mechanism. The research also shows how attaching the peripheral groups directly to the N-annulated PBI core changes the self-assembling properties and leads to the formation of H-type aggregates with strong aggregation-caused quenching effects. Additionally, a solvent-controlled stereomutation is observed for chiral compounds, resulting in helical supramolecular polymers with different handedness depending on the solvent.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Jorge S. Valera, Hironari Arima, Cristina Naranjo, Takuho Saito, Natsuki Suda, Rafael Gomez, Shiki Yagai, Luis Sanchez
Summary: The hierarchical self-assembly of scissor-shaped azobenzene dyads leads to the formation of discrete nanotoroids in solution, which further organize into well-defined 2D porous networks on a graphite surface. The steric demand of peripheral aliphatic units controls the stackability of nanotoroids in solution. Additionally, reversible dissociation and reconstruction of nanotoroids can be achieved through UV and visible light photoirradiation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Inorganic & Nuclear
Silvia Collavini, Sebastian F. Volker, Andrea Cabrera-Espinoza, Manuel A. Martinez, Abel De Cozar, Leire San Felices, Luis Sanchez, Juan Luis Delgado
Summary: The straightforward synthesis of three organotin clusters with six triarylamine-based moieties is reported. The optoelectronic properties and gel-forming abilities of the molecules were investigated, and the association abilities were studied using NMR and UV-vis spectroscopy. Comparisons between geometric optimization and X-ray diffraction results provide useful insights into the different gelation behaviors of the compounds.
INORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Rafael Rodriguez, Cristina Naranjo, Anil Kumar, Paola Matozzo, Tapan Kumar Das, Qirong Zhu, Nicolas Vanthuyne, Rafael Gomez, Ron Naaman, Luis Sanchez, Jeanne Crassous
Summary: This study reports on the synthesis and self-assembly of 2,15- and 4,13-disubstituted carbo[6]helicenes bearing 3,4,5-tridodecylox-ybenzamide groups. The self-assembly of these helicenes is influenced by the substitution pattern in the helicene core, resulting in different supramolecular structures. The helical supramolecular structures exhibit efficient electron-spin filtering abilities when deposited on conductive surfaces.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Biochemistry & Molecular Biology
Macarena Calero, Lara H. Moleiro, Aline Sayd, Yeray Dorca, Lluis Miquel-Rio, Veronica Paz, Javier Robledo-Montana, Eduardo Enciso, Fernando Accion, Diego Herraez-Aguilar, Thomas Hellweg, Luis Sanchez, Analia Bortolozzi, Juan C. Leza, Borja Garcia-Bueno, Francisco Monroy
Summary: This study presents a colloidal synthesis method for integrating DNA antisense oligonucleotides into lipid nanoparticles, which can be used for the treatment of neuroinflammation-related diseases. The nanoparticles are functionalized to target brain border-associated macrophages and silence specific genes. The results provide a novel approach for gene therapy in neuroinflammation-related diseases.
FRONTIERS IN MOLECULAR BIOSCIENCES
(2022)
Article
Chemistry, Multidisciplinary
Cristina Naranjo, Sergio Adalid, Rafael Gomez, Luis Sanchez
Summary: The synthesis and self-assembling features of N-annulated perylenebisimides (N-PBIs) 2-4 are reported and compared with the complex self-assembly of N-PBI 1. Increasing the length of the alkyl spacer leads to the cancellation of differentiation in supramolecular polymerization, except for 2 which forms two different polymorphs. Kinetically trapped monomeric species are observed for N-PBIs 2-4, and their supramolecular polymerization can be accelerated by seed addition. This study sheds light on the intricate process of differentiation in self-assembly.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Rafael Rodriguez, Cristina Naranjo, Anil Kumar, Kais Dhbaibi, Paola Matozzo, Franck Camerel, Nicolas Vanthuyne, Rafael Gomez, Ron Naaman, Luis Sanchez, Jeanne Crassous
Summary: Self-assembling, chiroptical activity, and spin filtering properties of 2,15- and 4,13-disubstituted [6]helicenes decorated with 3,4,5-tris(dodecyloxy)-N-(4-ethynylphenyl)benzamide moieties are reported. The weak non-covalent interaction between the units affects the corresponding circularly polarized luminescence and spin polarization. Self-assembly is weak for these derivatives, and it is explained by the steric effect of the peripheral groups. Additionally, self-assembling features also influence chiral induced spin selectivity.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Marina Gonzalez-Sanchez, Mariia J. Mayoral, Violeta Vazquez-Gonzalez, Marketa Paloncyova, Irene Sancho-Casado, Fatima Aparicio, Alberto de Juan, Giovanna Longhi, Patrick Norman, Mathieu Linares, David Gonzalez-Rodriguez
Summary: Self-assembled nanotubes with distinct internal arrangements and properties are achieved through different supramolecular scenarios prior to polymerization, driven by chelate cooperativity and self-recognition motifs at the edges. The chosen supramolecular pathway for structurally related molecules with complementary nucleobases is determined by their propensity for specific cyclic structures through Watson-Crick pairing. These findings provide insight into the unpredictability and experimental evaluation of self-assembly pathways, as well as the design of functional nanomaterials with controlled helicity and chiroptical properties.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Manuel A. Martinez, Daniel Aranda, Enrique Orti, Juan Arago, Luis Sanchez
Summary: The self-assembling features of amphiphilic N-annulated perylene bisimides (N-PBIs) 1-4 in water were investigated experimentally and theoretically. The hydrophilic/hydrophobic ratio, determined by the oligo(ethylene) glycol (OEG) chains in the monomers, plays a significant role in the enthalpy of self-assembly. Molecular dynamic simulations revealed the influence of the initial arrangement of hydrophilic side chains and water-side chain interactions on the enthalpy contribution and overall stability of the aggregated species in water.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Review
Chemistry, Multidisciplinary
Fatima Garcia, Rafael Gomez, Luis Sanchez
Summary: Chiral supramolecular polymers are an important branch within the field of supramolecular polymers, which can generate helical structures and contribute to the research on the origin of homochirality in living organisms as well as the discovery of new functionalities of organic materials. By using chiral monomeric units or external stimuli, chiral supramolecular polymers can be constructed to achieve amplification of asymmetry and break symmetry. Chiral supramolecular polymers have promising applications in various fields.
CHEMICAL SOCIETY REVIEWS
(2023)
Review
Chemistry, Multidisciplinary
Fatima Garcia, Rafael Gomez, Luis Sanchez
Summary: Chiral supramolecular polymers are ideal models for generating helical structures, clarifying the origin of homochirality in Nature, or discovering new functionalities of organic materials. This article highlights the commonly used strategies for constructing chiral supramolecular polymers using chiral monomeric units or external stimuli. Examples of selective symmetry transfer and breaking symmetry by applying external stimuli are presented, emphasizing the thermodynamics and kinetics associated with these processes. The specific and promising applications of chiral supramolecular polymers are also introduced with recent relevant examples.
CHEMICAL SOCIETY REVIEWS
(2023)
Correction
Chemistry, Multidisciplinary
Lucia Lopez-Gandul, Cristina Naranjo, Cecilia Sanchez, Rafael Rodriguez, Fatima Aparicio, Rafael Gomez, Jeanne Crassous, Luis Sanchez
Article
Chemistry, Multidisciplinary
Lucia Lopez-Gandul, Cristina Naranjo, Cecilia Sanchez, Rafael Rodriguez, Rafael Gomez, Jeanne Crassous, Luis Sanchez
Summary: This study described the synthesis of two pairs of enantiomeric cyano-luminogens and investigated their supramolecular polymerization under kinetic and thermodynamic control. The compounds exhibited different aggregation states and chiroptical properties, and the chiroptical features strongly depended on the nature of the central aromatic unit.
Review
Chemistry, Multidisciplinary
P. B. Chamorro, F. Aparicio
Summary: Various strategies have been used for constructing supramolecular hollow tubes, with an emphasis on controlling chirality at the supramolecular level. The review covers the main examples of using simple molecular structures for precise assembly into chiral supramolecular tubular systems.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Cristina Naranjo, Yeray Dorca, Goutam Ghosh, Rafael Gomez, Gustavo Fernandez, Luis Sanchez
Summary: The kinetically controlled amplification of asymmetry experienced in the co-assembly of chiral tribiphenylaminetricarboxamides (S)-1 and (R)-1 is investigated, with the formation of metastable monomeric species through intramolecular H-bonds retarding the efficient amplification of asymmetry due to a chain-capper effect.
CHEMICAL COMMUNICATIONS
(2021)
Review
Chemistry, Multidisciplinary
Dan He, Yawen Li, Fuwen Zhao, Yuze Lin
Summary: High trap density in organic solar cells leads to localized charge carriers and reduced carrier lifetime, limiting device efficiency. This feature article summarizes the recent advances of trap suppression by material design and device engineering.
CHEMICAL COMMUNICATIONS
(2024)
Review
Chemistry, Multidisciplinary
Olivier Monfort, Arshitha Madhusudhan, Martin Motola
Summary: This article presents the advantages of coupling photocatalysis and Fenton-based processes for environmental remediation and discusses their synergy. It critically examines the simultaneous triggering of these two processes and provides insights into research approaches. The study aims to enhance understanding of this complex process and highlight the potential integration of new catalysts in current wastewater treatment technology.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Manideepa Dhar, Chittaranjan Mishra, Avijit Das, Uttam Manna
Summary: An approach of 'polymerization of monomers in its aggregated form' has been introduced to tailor the water wettability of fibrous and porous substrates, achieving hydrophobicity to superhydrophobicity transition, as well as patterned wettability. This facile chemical method provides a durable coating with adjustable and patterned wettability for various potential applications.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Saswat Ranjan Bhoi, Chhanda Debnath, Shikha Gandhi
Summary: In this article, a novel catalytic reaction using Pd(0) and Bronsted acid is reported for the synthesis of biologically important imidazolidinone-fused N-heterocycles through redox-neutral intramolecular N-allylation of indoles and pyrroles with alkynes. This atom-economical method is applicable to a wide range of substrates and eliminates the need for leaving groups or oxidizing agents commonly used in traditional allylation reactions.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Longkun Chen, Mingshuai Zhang, Meichen Liu, Zhuoyuan Liu, Yuetong Qiu, Zhilai Zhang, Fuchao Yu, Jiuzhong Huang
Summary: In this study, an efficient Rh(III)-catalyzed selective mono- and dual-C-H bond functionalization/cyclization with iodonium ylide as the sole coupling partner was demonstrated. Fused benzodiazepine skeletons were obtained in excellent yields, providing an improved approach to dual C-H unsymmetrical functionalization.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Alice Kennett, Sven Epple, Gabriella van der Valk, Irene Georgiou, Evelyne Gout, Romain R. Vives, Angela J. Russell
Summary: This study presents the design and synthesis of sulfated disaccharide inhibitors based on IdoA(2S)-GlcNS(6S), which showed potent inhibition of Sulf-2. The results suggest that IdoA(2S)-GlcNS(6S) is the shortest fragment size required for effective inhibition of Sulfs, and a trisulfated disaccharide is identified as the minimal fragment size of heparan sulfate for effective endosulfatase inhibition.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Mauro Garbini, Andrea Brunetti, Riccardo Pedrazzani, Magda Monari, Massimo Marcaccio, Giulio Bertuzzi, Marco Bandini
Summary: The self-adaptability of galvanostatic electrolysis was found to be helpful in a multistage chemo- and diastereoselective electrochemically promoted cyclodimerization of chalcones. Through a series of reductive events, densely functionalized cyclopentanes with five contiguous stereocenters were obtained (25 examples, yields up to 95%, dr values up to >20:1). Further experimental and electrochemical investigations indicated the crucial role of dynamic kinetic resolution of the aldol intermediate in the reaction mechanism.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Dhananjay S. Nipate, Neha Meena, Prakash N. Swami, Krishnan Rangan, Anil Kumar
Summary: In this study, the synthesis of functionalized benzo[a]phenazines and indazolo[2,3-a]quinolines was achieved through Rh(III)-catalyzed oxidative annulation of 2-arylquinoxalines and 2-aryl-2H-indazoles with allyl alcohols. The method showed a wide substrate scope, excellent functional group tolerance, good to high yields of annulated products, and the capability for scaled-up synthesis. A tentative mechanism of the annulation reaction was proposed based on a preliminary mechanistic investigation.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Ruonan Zhang, Abudukadi Tudi, Xia Yang, Xuping Wang, Zhihua Yang, Shujuan Han, Shilie Pan
Summary: A new lead tellurium borate material with a unique fundamental building block [B4O10] was synthesized and found to exhibit high birefringence. The structure-property relationship was discussed using first-principles calculations.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Amresh Kumar Singh, Baishali Thakurta, Anupam Giri, Monalisa Pal
Summary: This study introduces three key concepts for the quick synthesis of large-scale high-quality 2D materials films and their utilization in device fabrication.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Reina Hagiwara, Shun Nishimura, Kosuke Okeyoshi
Summary: A copolymer-conjugated nanocatalytic system has been developed to improve electron transfer and enhance photoinduced H2 generation.
CHEMICAL COMMUNICATIONS
(2024)
