Article
Chemistry, Multidisciplinary
Enzo Olivieri, Guilhem Quintard, Jean-Valere Naubron, Adrien Quintard
Summary: The study introduces a fueling method using trichloroacetic acid to create dissipative gelating materials that can switch between different acid/base states. The system is robust and resilient, with the chiral nature of amino acid gelator contributing to chiroptical switching properties.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Physical
Qin Huang, Ping Yu, Li-Hua He, Jing-Lin Chen, Sui-Jun Liu, He-Rui Wen
Summary: Two new monometallic copper(I) complexes have been synthesized and characterized, showing improved luminescence properties. The introduction of electron-donating methyl groups on the 6-cyano-2,2'-bipyridine ligands is favorable for enhancing the luminescence properties of the Cu(I) complexes.
JOURNAL OF MOLECULAR STRUCTURE
(2022)
Article
Chemistry, Organic
Esha H. Bhalodi, Krupa N. Patel, Ashutosh Bedekar
Summary: The synthesis of 2-amino-5-aza[6]helicene and its derivatives is reported. The diastereomeric (R)menthylcarbamate derivative of this aza[6]helicene is prepared and its isomers were physically separated by column chromatography and their optical properties were measured. Optically pure isomer (P)2-amino-5-aza[6]helicene was generated and its Boc-derivative was prepared.
Article
Chemistry, Inorganic & Nuclear
Shinichi Iba, Kohei Iwata, Taichi Sotani, Takahiro Ishida, Natsuhiro Sano, Hiromitsu Sogawa, Fumio Sanda
Summary: In this study, platinum complexes derived from L-alanine were synthesized with azobenzene moieties, showing isomerization between trans and cis forms under UV and visible light irradiation. DFT calculations and noncovalent interaction analysis revealed the formation of intramolecular hydrogen bonds and pi-pi interactions contributing to the conformational stability. Mirror-image CD spectroscopic patterns were exhibited by the D-alanine-derived counterparts, indicating different chiroptical properties compared to the L-alanine-derived complexes.
Article
Chemistry, Applied
Jun Ni, Zhongcui Guo, Qiong Zhu, Shuqin Liu, Jianjun Zhang
Summary: This article reports the synthesis and characterization of three novel square-planar platinum(II) complexes. These complexes exhibit sensitive response to volatile organic compound (VOC) vapors and show potential application prospects in visual detection.
Article
Chemistry, Organic
Gabriel Hoffrichter, Arne Luetzen
Summary: A new positively allosteric bis(beta-cyclodextrin) receptor 1 was synthesized and studied for its binding affinity towards sodium deoxycholate in aqueous solution. It was found that the addition of a zinc(ii) phenanthroline complex as an effector for the allosteric 2,2'-bipyridine motif resulted in more than an 18-fold increase in the receptor's binding constant towards the substrate.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Biochemistry & Molecular Biology
Laure Guy, Maelle Mosser, Delphine Pitrat, Jean-Christophe Mulatier, Mercedes Kukulka, Monika Srebro-Hooper, Erwann Jeanneau, Amina Bensalah-Ledoux, Bruno Baguenard, Stephan Guy
Summary: A series of molecules with chiral connections between two quinolines, benzoquinolines, or phenanthrolines were developed, and their photophysical and chiroptical switching activity upon protonation was studied. The results showed significant changes in the spectral properties of these molecules in acidic medium, making them promising multifunctional pH probes.
Article
Chemistry, Inorganic & Nuclear
Alexandre Abherve, Maurizio Mastropasqua Talamo, Nicolas Vanthuyne, Francesco Zinna, Lorenzo Di Bari, Maxime Grasser, Boris Le Guennic, Narcis Avarvari
Summary: Enantiopure helicene-based bis(pyrazol-1-yl)pyridine (bpp-[6]helicene) ligands have been synthesized and characterized. The chiroptical properties of these ligands have been studied and circularly polarized luminescence in the visible region has been observed in chiral Eu(III) complexes based on these ligands, supported by theoretical calculations suggesting the antenna effect of the bpp ligand.
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Qiwei Zhu, Chenxia Kan, Yucai Cao, Zefeng Tang, Kang Xu, Pengjie Hang, Biao Li, Yuxin Yao, Ming Lei, Xuegong Yu
Summary: A tandem electro-oxidative reaction was used to efficiently construct a key intermediate and derivatives of aza[7]helicene, demonstrating high selectivity and rapid synthesis of functionalized organic conjugated materials. The synthesized compounds were further studied for their photoelectrical properties and potential application in perovskite solar cells.
Article
Chemistry, Organic
Changgong Xu, Phillip Nader, Jonathan Xavier, Burjor Captain, Norito Takenaka
Summary: Helicene-derived 2,2'-bipyridine N-monoxide was used as a Lewis base catalyst for the enantioselective propargylation of non-activated acylhydrazones, showing moderate-to-good reactivity and enantioselectivity for a range of acylhydrazones. This is the first example of asymmetric propargylation of non-activated acylhydrazones using this catalyst.
Article
Chemistry, Multidisciplinary
Fanrui Gao, Xingke Yu, Ling Liu, Jinlei Chen, Yongjun Lv, Ting Zhao, Jiecheng Ji, Jiabin Yao, Wanhua Wu, Cheng Yang
Summary: In this study, pillar[5]arene-based molecular universal joints (MUJs) were synthesized and enantio-differentiated. The MUJs with fused crown ether subring showed significant chiral inversion upon the addition of sodium cations, while the MUJ2 with alkyl subring showed no chiral inversions. It was found that the sodium ion triggered rolling-in motion of the subring to the pillar[5]arene cavity, and the stabilized self-included conformers were attributed to the synergistic noncovalent interaction of cation-pi interactions and C -H...pi interactions. The addition of MeOH or competitive hosts disassembled the complex and triggered reversible chiroptical switching.
CHINESE CHEMICAL LETTERS
(2023)
Article
Chemistry, Multidisciplinary
Yi Jiang, Hyeonjung Jung, Se Hun Joo, Qi Kun Sun, Changqing Li, Hyuk-Jun Noh, Inseon Oh, Yu Jin Kim, Sang Kyu Kwak, Jung-Woo Yoo, Jong-Beom Baek
Summary: Developing new linkage-based conductive COFs is a major focus in reticular chemistry due to their potential applications in energy storage. The solvent- and catalyst-free synthesis of ABBPM-COF shows promise in providing a chemically stable conductive material with semiconducting properties. The structure of ABBPM-COF, elucidated through various techniques, demonstrates its crystalline nature and excellent stability in various solutions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Physical
Sondes Raouafi, Basim H. Asghar, Faouzi Aloui
Summary: New nitrile grafted [6]Helicene derivatives with hexacyclic structures were synthesized through a UV-light photochemical pathway, showing potential as donor materials for polymer solar cells and promising candidates for electronic and optoelectronic devices due to their strong fluorescence in the blue region of the visible spectrum.
JOURNAL OF MOLECULAR STRUCTURE
(2021)
Article
Optics
Anuj Dalal, Kapeesha Nehra, Anjli Hooda, Devender Singh, Rajender Singh Malik, Sumit Kumar
Summary: This paper highlights the synthesis of fluorescent derivatives of 2,2'-bipyridine, showcasing their applications in electroluminescent devices. The compounds were characterized using various spectroscopic techniques and photophysical properties were identified through photoluminescence spectra. Additionally, the compounds' electrochemical behavior was studied and their kinetic stability and chemical inertness were confirmed through optical band gap data analysis.
Article
Chemistry, Inorganic & Nuclear
Peter D. Hall, Michael A. Stevens, Jiao Yu J. Wang, Le Nhan Pham, Michelle L. Coote, Annie L. Colebatch
Summary: This article investigates monometallic and bimetallic complexes formed by the ligand MeL with copper and zinc, and discovers that the ligand can exist in four redox states.
INORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Kais Dhbaibi, Maxime Grasser, Haiet Douib, Vincent Dorcet, Olivier Cador, Nicolas Vanthuyne, Francois Riobe, Olivier Maury, Stephan Guy, Amina Bensalah-Ledoux, Bruno Baguenard, Geert L. J. A. Rikken, Cyrille Train, Boris Le Guennic, Matteo Atzori, Fabrice Pointillart, Jeanne Crassous
Summary: The combination of physical properties sensitive to molecular chirality in a single system allows the observation of interesting phenomena such as magneto-chiral dichroism (MChD) and circularly polarized luminescence (CPL), which have potential applications in optical data readout and display technology. By coordinating a chiral organic chromophore to Yb(hfac)(3) units, homochiral one-dimensional coordination polymers of Yb-III were designed, which exhibit strong magnetic anisotropy and show single-molecule magnet behavior and room temperature magneto-chiral dichroism (MChD). Computational investigations support the correlation between MChD and the structure.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Etienne S. Gauthier, Laura Abella, Elsa Caytan, Thierry Roisnel, Nicolas Vanthuyne, Ludovic Favereau, Monika Srebro-Hooper, J. A. Gareth Williams, Jochen Autschbach, Jeanne Crassous
Summary: Describes the photophysical and chiroptical properties of a novel, chiral helicene-NHC-Re(I) complex with an N-(aza[6]helicenyl)-benzimidazolylidene ligand, showing its capability of emitting yellow circularly polarized luminescence. A comparative analysis with other helicene-Re(I) complexes reported to date highlights the impact of structural modifications on the emissive and absorptive properties.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Medicinal
Aurelie Mace, Khaoula Hamrouni, Paola Matozzo, Max Coehlo, Jakub Firlej, Faouzi Aloui, Nicolas Vanthuyne, Elsa Caytan, Marie Cordier, Gregory Pieters, Monika Srebro-Hooper, Fabienne Berree, Bertrand Carboni, Jeanne Crassous
Summary: 2-Amino[2.2]paracyclophane reacts with salicylaldehyde or 2-hydroxyacetophenone to yield imines that can form a new series of boranils upon complexation with BF2. These boron-containing compounds exhibit both planar and axial chiralities and have been studied experimentally and computationally. The photophysical and chiroptical properties of these compounds were compared to simpler boranils exhibiting axial chirality only, and it was found that the simpler chiral architectures demonstrate stronger circularly polarized luminescence activity.
Article
Chemistry, Medicinal
Elina Buitrago, Clarisse Faure, Marcello Carotti, Elisabetta Bergantino, Renaud Hardre, Marc Maresca, Christian Philouze, Nicolas Vanthuyne, Ahcene Boumendjel, Luigi Bubacco, Amaury du Moulinet d'Hardemare, Helene Jamet, Marius Reglier, Catherine Belle
Summary: In this study, the inhibition activities of 2-Hydroxypyridine-N-oxide analogs (HOPNO) on tyrosinase were enhanced by the combination with a reference inhibitor or a natural substrate. The (S) enantiomer of the racemic amino acid HOPNO-AA showed the strongest inhibitory effect.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2023)
Article
Chemistry, Physical
Kais Dhbaibi, Pierpaolo Morgante, Nicolas Vanthuyne, Jochen Autschbach, Ludovic Favereau, Jeanne Crassous
Summary: This study reports the experimental measurement of the photophysical and chiroptical properties of helicene-based pi-conjugated emitters with electron-accepting or donating moieties at low temperature. The samples exhibit strong circularly polarized phosphorescence with high luminescence dissymmetry factor and long lifetime for the most active molecule, the nitro compound. The theoretical investigation reveals that the emissions of singlet and triplet excited states mainly come from the helicene core with different rotatory strengths due to the absence of strong mixing between these states.
JOURNAL OF PHYSICAL CHEMISTRY LETTERS
(2023)
Article
Chemistry, Multidisciplinary
Ke-Feng Zhang, Nidal Saleh, Michal Swierczewski, Arnulf Rosspeintner, Francesco Zinna, Gennaro Pescitelli, Celine Besnard, Laure Guenee, Thomas Burgi, Jerome Lacour
Summary: A chiral bispyrene macrocycle was synthesized for intermolecular excimer fluorescence upon aggregation using a double hydrothiolation method followed by intramolecular oxidation. High stereoselectivity was achieved for the thiol-ene additions under templated conditions. The structural evolution upon aggregation was monitored by ECD/CPL.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Medicinal
Fuwei Gan, Peng Yang, Juncong Liang, Chengshuo Shen, Jeanne Crassous, Huibin Qiu
Summary: We describe a facile method to produce circularly polarized luminescence (CPL) from helicene racemates via supramolecular association with DNA in aqueous solution. Racemic cationic helicene derivatives are immobilized in the grooves of commercially available double-stranded right-handed DNA, and the discrimination of left- and right-handed helicenes by chiral DNA is monitored by single molecule force spectroscopy. This strategy provides a distinctive insight into the fabrication of CPL-emitting systems.
Article
Chemistry, Multidisciplinary
Patricia Izquierdo-Garcia, Jesus M. Fernandez-Garcia, Samara Medina Rivero, Michal Samal, Jiri Rybacek, Lucie Bednarova, Sergio Ramirez-Barroso, Francisco J. Ramirez, Rafael Rodriguez, Josefina Perles, David Garcia-Fresnadillo, Jeanne Crassous, Juan Casado, Irena G. Stara, Nazario Martin
Summary: This study compares the properties of three helical bilayer nanographenes with different helicenes, and finds that the length of the helicene has a significant impact on their properties. A shorter helicene length leads to stronger electron donor character and greater optical properties in [9]HBNG.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Inorganic & Nuclear
Jennifer Morvan, Francois Vermersch, Ziyun Zhang, Thomas Vives, Thierry Roisnel, Christophe Crevisy, Laura Falivene, Luigi Cavallo, Nicolas Vanthuyne, Guy Bertrand, Rodolphe Jazzar, Marc Mauduit
Summary: The development of highly efficient enantioselective olefin metathesis catalysts is a major challenge. By using optically pure chiral cyclic (alkyl)(amino)carbene (ChiCAAC) ligands and preliminary mechanistic insights and density functional theory (DFT) computations, it was observed that the formation of rotamers before the enantio-determining step can impair catalytic performances in this field. DFT calculations also demonstrated that these findings can help accelerate ligand discovery by providing faster methods to differentiate potential candidates.
Article
Chemistry, Physical
Antonio Del Vecchio, Jakub Talcik, Sophie Colombel-Rouen, Jan Lorkowski, Melinda R. Serrato, Thierry Roisnel, Nicolas Vanthuyne, Guy Bertrand, Rodolphe Jazzar, Marc Mauduit
Summary: New Blechert-type ruthenium complexes with cyclic(alkyl)(amino)carbene (CAAC) ligands show remarkable thermal stability in solution and excellent catalytic performances in various metathesis reactions. They exhibit high catalytic activity at low loading and can achieve high enantiomeric excess in asymmetric metathesis reactions.
Article
Chemistry, Multidisciplinary
Javier Mateos-Martin, Kais Dhbaibi, Manuel Melle-Franco, Aurelio Mateo-Alonso
Summary: This study describes the synthesis of a new set of twisted dibenzotetraazahexacenes and analyzes their optical and redox properties. The twisted structure of these compounds is confirmed through single-crystal X-ray diffraction. The effects of the substituents and twists on the properties are studied using absorption, fluorescence, electrochemical, and theoretical studies.
CHEMISTRY-A EUROPEAN JOURNAL
(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
Physics, Fluids & Plasmas
A. Deptuch, T. Jaworska-Golab, M. Dziurka, J. Hooper, M. Srebro-Hooper, M. Urbanska, M. Tykarska, M. Marzec
Summary: Density functional theory (DFT) calculations and x-ray diffraction techniques were used to determine the tilt angle in ferroelectric smectic C* and antiferroelectric smectic CA* phases for five chiral compounds. The study considered two conformations for the terminal chains and three types of deviation from the rodlike shape of the molecules. The results showed that C-shaped structures, in both fully extended or gauche conformations, agreed well with the experimentally measured tilt angle values.
Article
Chemistry, Multidisciplinary
Pieter J. Gilissen, Quentin Duez, Guilherme L. Tripodi, Magda M. J. Dekker, Jiangkun Ouyang, Kais Dhbaibi, Nicolas Vanthuyne, Jeanne Crassous, Jana Roithova, Johannes A. A. W. Elemans, Roeland J. M. Nolte
Summary: The kinetic enantio-recognition of chiral viologen guests by planar-chiral porphyrin cage compounds is determined by the planar chirality of the host and influenced by its size, but not the chirality of its substituents.
CHEMICAL COMMUNICATIONS
(2023)
