Article
Biochemistry & Molecular Biology
Alessandra Forni, Rosario Russo, Giacomo Rapeti, Stefano Pieraccini, Maurizio Sironi
Summary: Through density functional theory calculations, it was found that there is an interdependence between halogen and hydrogen bonding in the shared pi-electron system of benzene, indicating that the two interactions are not strictly independent of each other.
Article
Chemistry, Multidisciplinary
Hayato Anetai, Yoshitaka Matsushita, Takahito Ohmura, Masayuki Takeuchi
Summary: Single crystals of simple benzene derivatives with different substituents were prepared and the flexibility of these crystals was investigated. The crystals can be classified into three types based on their bending behavior, which depends on the substituents. Furthermore, density functional theory calculation and nanoindentation test revealed the mechanical properties of the bendable crystals.
CRYSTAL GROWTH & DESIGN
(2023)
Article
Chemistry, Inorganic & Nuclear
Zhao Long, Chen Guan-Fan, Wen Yi-Hang, Xiao Xun-Wen
Summary: Two cocrystals with the same chemical composition [L1.L2] were synthesized using different solvent systems. Characterization confirmed the purity of both cocrystals. Photocurrent responses were tested, with only one cocrystal generating a signal, possibly due to different biphenyl conformations in one of the components.
CHINESE JOURNAL OF STRUCTURAL CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Taylor A. Bramlett, Adam J. Matzger
Summary: This study experimentally determined the relative strength of halogen bonding interactions in solution by Raman spectroscopic observation of complexes formed from interacting iodobenzene-derived XB donors and pyridine XB acceptors. The evaluation of binding energy coupling with ALMO-EDA analysis revealed a prominent role for charge transfer interactions in halogen bonding energy contributions. Raman spectra accurately predicted stronger interactions within IPFB complexes than with IDNB complexes, despite IPFB having similar electrostatics to IDNB and containing a smaller sigma-hole.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Alica C. Keuper, Kevin Fengler, Florian Ostler, Tobias Danelzik, Dariusz G. Piekarski, Olga Garcia Mancheno
Summary: A new approach to achieve highly enantioselective halogen-bonding catalysis has been developed by designing fine-tuned halogen-halogen interactions. This strategy utilizes both the electron cloud and sigma-hole site of the substrate's halogen substituent to form a tight chiral complex, enabling controlled induction of high levels of chirality transfer. Remarkable enantioselectivities of up to 95:5 e.r. (90% ee) have been achieved in a model dearomatization reaction using tetrakis-iodotriazole multidentate anion-binding catalysts.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Biochemistry & Molecular Biology
Tsai I-Ting, M. Merced Montero-Campillo, Ibon Alkorta, Jose Elguero, Manuel Yanez
Summary: Intramolecular interactions, particularly beryllium bonds in ortho-substituted benzene derivatives, play a crucial role in stabilizing conformers with newly formed five or six-membered heterocycles. The strength of the beryllium bond is quantified using Natural Bond Orbital approach, showing significant interaction energies between the donor and acceptor. Energy is mostly spent on deforming donor-acceptor pairs to form new rings in these systems.
Article
Chemistry, Physical
Gaber A. M. Mersal, A. A. H. Basry, M. Khodari
Summary: The study investigated the mechanism of interaction between metformin and halogen molecules using experimental and theoretical methods, highlighting the crucial role of orthogonal hydrogen bonds and halogen bonds in stabilizing molecular structures, as well as the significant impact of solvents on the stability of complexes.
JOURNAL OF MOLECULAR LIQUIDS
(2021)
Article
Chemistry, Physical
Liya Dai, Pengyao Xing, Aiyou Hao
Summary: In this study, the aryl-group achiral molecular tweezers were found to effectively include chiral guest molecules via halogen bonding and other noncovalent interactions. Experimental and computational calculations revealed the formation of stable 1:1 host-guest complexes, demonstrating the transfer of chirality to achiral host molecules at the supramolecular level.
JOURNAL OF PHYSICAL CHEMISTRY C
(2023)
Article
Chemistry, Multidisciplinary
Jan Alfuth, Beata Zadykowicz, Barbara Wicher, Katarzyna Kazimierczuk, Tadeusz Polonski, Teresa Olszewska
Summary: In this study, a series of new 4-iodoethynyl and 4,7-bis-(iodoethynyl)benzo-2,1,3-chalcogenadiazole derivatives were investigated for their crystal self-assembly behavior using X-ray diffraction and analysis of intermolecular interactions. The results revealed the influence of chalcogen atom nature on the solid-state arrangement and highlighted the importance of chalcogen and halogen bonding interactions in the molecular self-assembly process.
CRYSTAL GROWTH & DESIGN
(2022)
Article
Chemistry, Physical
Lucia Gonzalez, Sara Graus, Blanca Gaspar, Sheila Espasa, Adrian Velazquez-Campoy, Julen Munarriz, Jose Luis Serrano, Rosa M. Tejedor, Santiago Uriel
Summary: The study reveals that bromide anions act as doubly connected nodes in halogen-bonded co-crystals, forming linear or angular chains; NCI analysis demonstrates that the balance of halogen bonds, hydrogen bonds, and van der Waals interactions determines the crystal structures.
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
(2021)
Article
Chemistry, Inorganic & Nuclear
Thanthapatra Bunchuay, Andrew Docker, Nicholas G. White, Paul D. Beer
Summary: This study reports the synthesis of a series of halogen bonding acyclic anion receptors based on a novel 1,2-iodo-triazoliumtriazole benzene motif, and elucidates key conformational effects and coordination modes associated with ortho-substituted iodotriazole based XB donors through NMR spectroscopic techniques and X-ray crystal structure analysis.
Article
Chemistry, Applied
Dhananjoy Pal, Tim Steinke, Lukas Vogel, Elric Engelage, Sascha Heinrich, Dana Kutzinski, Stefan M. Huber
Summary: This article describes the synthesis of a mixed chalcogen- and halogen-bond donor and provides a first indication of its catalytic activity in a benchmark reaction.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Sophie C. Patrick, Robert Hein, Andrew Docker, Paul D. Beer, Jason J. Davis
Summary: In this study, a comprehensive investigation of the electrochemical anion sensing performance of novel halogen bonding (XB) and hydrogen bonding (HB) bis-ferrocene-(iodo)triazole receptors was conducted in competitive aqueous organic solvent media. The XB sensor outperformed the HB sensor in solution, particularly showing superior anion recognition capability even in highly competitive aqueous solvent media. Additionally, a significant surface-enhancement effect was observed for both XB/HB receptive films in all solvent systems.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Cody Loy, Jana M. Holthoff, Robert Weiss, Stefan M. Huber, Sergiy V. Rosokha
Summary: Halogen-bonded complexes between halide anions and a cyclopropenylium-based anionic XB donor were characterized in solution for the first time, showing that halogen bonding is strong enough to overcome electrostatic repulsion. The formation constants of these complexes are comparable to others, but their UV-Vis spectra are determined by the electronic excitations within the XB donor.
Article
Biochemistry & Molecular Biology
Jun Luo, Hongjing Dai, Chenglu Zeng, Dawang Wu, Maoqi Cao
Summary: This study investigates the structural characteristics and interaction energies of the halogen bond between heteronuclear halogens (ClF, BrCl, IBr, ICl, BrF, and IF) and benzene using density functional theory. The results show that the interaction energies increase with the polarity between the atoms and are proportional to the angles between the Z axis and the covalent bond of the heteronuclear halogen. The electron density and Laplacian values indicate that the interaction is a long-range weak interaction similar to a hydrogen bond. The main interaction in the complexes varies depending on the halogen species, with van der Waals forces dominating in some and electrostatic interactions dominating in others.
Article
Chemistry, Multidisciplinary
Oliver Dumele, Benedikt Schreib, Ulrike Warzok, Nils Trapp, Christoph A. Schalley, Francois Diederich
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2017)
Article
Chemistry, Organic
Sizhou M. Liu, Dino Wu, Jeffrey W. Bode
Article
Chemistry, Multidisciplinary
Dino Wu, Nicole A. Fohn, Jeffrey W. Bode
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2019)
Review
Chemistry, Multidisciplinary
Oliver Dumele, Jiahao Chen, James V. Passarelli, Samuel I. Stupp
ADVANCED MATERIALS
(2020)
Correction
Chemistry, Multidisciplinary
Birgit S. Lauber, Leo A. Hardegger, Alam K. Asraful, Bjarte A. Lund, Oliver Dumele, Michael Harder, Bernd Kuhn, Richard A. Engh, Francois Diederich
CHEMISTRY-A EUROPEAN JOURNAL
(2020)
Article
Chemistry, Physical
Niklas Grabicki, Oliver Dumele, Hiroaki Sai, Natalia E. Powers-Riggs, Brian T. Phelan, M. Hussain Sangji, Craig T. Chapman, James Passarelli, Adam J. Dannenhoffer, Michael R. Wasielewski, Samuel Stupp
Summary: This study investigated the formation of supramolecular polymers in water by carboxylated naphtho-p-quinodimethane amphiphiles. It was found that the polymorphism of crystalline assemblies, including ribbons, helically rolled ribbons, and twisted filaments, was controlled by the degree of protonation of the carboxylic head groups. Different protonation levels led to varying morphologies and visible absorption shifts in the resulting assemblies, making them potential candidates for solar energy materials and photocatalytic systems.
CHEMISTRY OF MATERIALS
(2021)
Article
Chemistry, Multidisciplinary
Niklas Grabicki, Khoa T. D. Nguyen, Steffen Weidner, Oliver Dumele
Summary: A set of strained aromatic macrocycles based on [n]cyclo-2,7-(4,5,9,10-tetrahydro)pyrenylenes with size-dependent photophysical properties is presented. The rim confinement strategy makes cycloparaphenylenes an attractive supramolecular host family with strong binding capabilities. The structural and thermodynamic reasons for the exceptionally strong binding have been elucidated through combination of experimental and computational methods.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Oliver Dumele, Luka Dordevic, Hiroaki Sai, Thomas J. Cotey, M. Hussain Sangji, Kohei Sato, Adam J. Dannenhoffer, Samuel I. Stupp
Summary: This study investigates the synthesis of supramolecular polymers capable of sensitizing catalysts for photocatalytic hydrogen production and successfully develops a supramolecular photocatalytic system that retains long-term photocatalytic activity in all aqueous media. The findings demonstrate the potential of tailored supramolecular polymers as renewable energy and sustainability materials.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Niklas Grabicki, Oliver Dumele
Summary: Strained aromatic macrocycles based on cycloparaphenylenes (CPPs) show strong binding with fullerenes, and highly functionalized CPP derivatives are capable of supramolecular binding with other molecules.
Article
Chemistry, Multidisciplinary
Oleksandr Kysliak, Simon H. F. Schreiner, Niklas Grabicki, Phil Liebing, Florian Weigend, Oliver Dumele, Robert Kretschmer
Summary: Many chemicals known today have aromaticity, which is achieved through the delocalization of pi-electrons in a ring structure. We report the synthesis of a dipotassium cyclopentagallene, a rare example of a five-membered aromatic ring stabilized by only two pi-electrons. Experimental and computational data confirm its aromatic character.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Konstantin Guenther, Niklas Grabicki, Beatrice Battistella, Lutz Grubert, Oliver Dumele
Summary: We synthesized and operated two all-organic molecular spin-state switches that can be switched from a diamagnetic to a paramagnetic form through a reversible electrocyclic reaction. These switches can be easily activated by LED light source at low temperatures. The switches have significant research and application prospects.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Josefine Sprachmann, Tommy Wachsmuth, Manik Bhosale, David Burmeister, Glen J. Smales, Maximilian Schmidt, Zdravko Kochovski, Niklas Grabicki, Robin Wessling, Emil J. W. List-Kratochvil, Birgit Esser, Oliver Dumele
Summary: Despite being unstable, 4n pi systems have gained attention for their unique optical and electronic properties. The first antiaromatic framework materials were synthesized and a series of highly crystalline and porous COFs based on DBP were obtained. These antiaromatic COFs show potential applications in positive electrode materials for Li-organic batteries and exhibit photoconductivity upon visible light irradiation.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Trung Tran Ngoc, Niklas Grabicki, Elisabeth Irran, Oliver Dumele, Johannes F. Teichert
Summary: In this study, a class of stable neutral homoaromatic molecules was successfully synthesized and their existence was confirmed by experimental evidence and computational analysis. Additionally, it was discovered that one of these molecules can undergo reversible photochemical rearrangement, acting as a photoswitch. These findings provide important insights into the study of homoconjugative interactions in organic molecules and the design of responsive molecular materials.
Article
Chemistry, Multidisciplinary
Niklas Grabicki, Sergey Fisher, Oliver Dumele
Summary: Researchers synthesized an ethylene glycol-decorated [6]cyclo-meta-phenylene (CMP) macrocycle, which was used as a subunit to construct a fourfold Au-2(I)-aryl metallacycle with a square arrangement. The corners of the metallacycle consisted of rigid dinuclear gold(I) complexes, which were previously known to form only triangular metallacycles. The conformational flexibility of the [6]CMP macrocycle and the rigid dinuclear gold(I) moieties allowed for the square geometry, as confirmed by single-crystal X-ray diffraction. The gold complex formation showed size-selectivity compared to an alternative route using platinum(II) corner motifs. Upon reductive elimination, an all-organic ether-decorated carbon nanoring was obtained. Investigation as a host for the complexation of large guest molecules with suitable convex pi-surfaces was conducted using isothermal NMR binding titrations, and association constants for [6]cycloparaphenylene ([6]CPP), [7]CPP, C-60, and C-70 were determined.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Josefine Sprachmann, Tommy Wachsmuth, Manik Bhosale, David Burmeister, Glen J. Smales, Maximilian Schmidt, Zdravko Kochovski, Niklas Grabicki, Robin Wessling, Emil J. W. List-Kratochvil, Birgit Esser, Oliver Dumele
Summary: In recent years, 4n pi systems have attracted significant attention due to their unique optical and electronic properties. We synthesized the first antiaromatic framework materials based on dibenzopentalene and obtained highly crystalline and porous covalent organic frameworks (COFs). These COFs exhibit excellent conductivity and photoconductivity, and show enhanced performance as positive electrode materials in Li-organic batteries.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
