Review
Chemistry, Multidisciplinary
Ashanul Haque, Khalaf M. Alenezi, Muhammad S. Khan, Wai-Yeung Wong, Paul R. Raithby
Summary: The design and development of functional materials with practical applications require high standards. Understanding and controlling inter- and intra-molecular interactions offer opportunities for designing new materials. Manipulating the molecular structure can significantly alter these interactions and enhance the properties and functions of the material. Non-covalent interactions (NCIs) have been found to have beneficial effects, indicating that manipulating NCIs can generate functional materials with various physical properties for applications in catalysis, drug delivery, crystal engineering, etc. This review aims to explore the implications of NCIs on molecular packing, optical properties, and applications of functional pi-conjugated materials. Additionally, it attempts to delineate the effects of weak interactions on opto-electronic (O-E) applications.
CHEMICAL SOCIETY REVIEWS
(2023)
Article
Biochemistry & Molecular Biology
Jay Quentin, Eric W. Reinheimer, Leonard R. MacGillivray
Summary: The ditopic halogen-bond donors 1,2-, 1,3-, and 1,4-diiodotetrafluorobenzene (1,2-, 1,3-, and 1,4-di-I-tFb) form binary cocrystals with the unsymmetrical ditopic X-bond acceptor trans-1-(2-pyridyl)-2-(4-pyridyl)ethylene (2,4-bpe). For (1,2-di-I-tFb).(2,4-bpe) and (1,3-di-I-tFb).(2,4-bpe), the X-bond donor supports the C=C bonds of 2,4-bpe to undergo a topochemical [2+2] photodimerization in the solid state.
Article
Chemistry, Physical
Alberto Lopez-Magano, Borja Ortin-Rubio, Inhar Imaz, Daniel Maspoch, Jose Aleman, Ruben Mas-Balleste
Summary: The functionalization of an imine-based layered covalent organic framework has allowed the obtention of a heterobimetallated material with photoactive Ir and Ni fragments immobilized within the porous structure. These heterogeneous light-mediated reactions showed enhanced activity and stability compared to analogous homogeneous systems.
Article
Chemistry, Multidisciplinary
Zeynab Imani, Venkateswara Rao Mundlapati, Valerie Brenner, Eric Gloaguen, Katia Le Barbu-Debus, Anne Zehnacker-Rentien, Sylvie Robin, David J. Aitken, Michel Mons
Summary: The delta conformation, a local secondary structure in proteins, is stabilized by specific side-chain/backbone N-H interactions in derivatives of a cyclic amino acid with a sulphur atom in the gamma-position. This allows the delta conformation to compete with classical C5 and C7 hydrogen bonded conformers, expanding the range of small-molecule models beyond rigid proline-type compounds.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Xiaofei Xie, Hong Pan, Tai-Ping Zhou, Man-Yi Han, Lei Wang, Xiao Geng, Yongmin Ma, Rong-Zhen Liao, Zhi-Ming Wang, Jianguo Yang, Pinhua Li
Summary: A highly regioselective and diastereoselective [2 + 2] cross-photocycloaddition between electron-poor and electron-rich/electron-neutral alkenes under visible-light irradiation was developed. The study demonstrates the importance of ortho-ethynyl and cyano groups in substrates as self-photocatalysts, leading to the formation of a five-membered ring diradical intermediate. X-ray structural analysis confirmed the obtained regioselectivity and diastereoselectivity of the products.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Materials Science, Paper & Wood
Sumit Mittal, Saurav Prasad, Rajdeep Singh Payal, Satyam Ravi
Summary: In this paper, the molecular interactions of cellobiose were studied using density functional theory. It was found that hydrogen bonding plays a crucial role in the dissolution of cellobiose. The study showed that the acetate ion breaks the existing intra-molecular interactions in cellobiose and forms new inter-molecular interactions. These findings have profound implications for the understanding of hydrogen bonding and dissolution of cellobiose at the molecular level.
Review
Chemistry, Multidisciplinary
Charles C. J. Loh
Summary: Non-covalent interactions are essential in bond-forming events, particularly in the realm of synthetic carbohydrate chemistry. The exploitation of NCIs has led to advancements in catalyzed glycosylations, glycofunctionalizations, and stabilization of intermediates. Additionally, emerging opportunities in utilizing halogen bonding and unconventional NCIs have shown promise in various aspects of carbohydrate chemistry.
NATURE REVIEWS CHEMISTRY
(2021)
Article
Nanoscience & Nanotechnology
Xiaoyang Bi, Mengjia Xu, Zhengchao Xie, Yan Li, Jiyu Tian, Zhenmin Wang, Zuankai Wang
Summary: Metal-thermoplastic hybrid structures have shown effectiveness in achieving lightweight design in aircraft components. However, the differences in physical and chemical properties between metal and thermoplastic pose challenges in fabricating high-reliability hybrid structures. A study discovers that covalent bonding at metal/thermoplastic interfaces plays a crucial role in the interfacial reliability of these structures. By grafting carboxyl functional group on polyetheretherketone (PEEK), the density and strength of interfacial covalency is increased, leading to the fabrication of high-reliability hybrid structures between PEEK and A6061-T6 aluminum alloy.
ACS APPLIED MATERIALS & INTERFACES
(2022)
Article
Biochemistry & Molecular Biology
Fabian Rabe von Pappenheim, Marie Wensien, Jin Ye, Jon Uranga, Iker Irisarri, Jan de Vries, Lisa-Marie Funk, Ricardo A. Mata, Kai Tittmann
Summary: This study reveals the presence of a lysine-cysteine redox switch in various proteins across different domains of life. These switches play important roles in enzyme catalysis and substrate binding in many proteins, linking lysine chemistry and redox biology.
NATURE CHEMICAL BIOLOGY
(2022)
Article
Chemistry, Organic
Nao Shimizu, Hajime Shigemitsu, Toshiyuki Kida, Thorsten Bach, Tadashi Mori
Summary: A range of asymmetric photochemical transformations using visible light have recently become considerably attractive. Chiral Lewis acid association to enones for [2 + 2] and ortho photocycloadditions and oxadi-pi-methane rearrangements have shown to be very promising in achieving effective enantiodifferentiation. In this study, we investigated the regio- and enantiodifferentiation of [2 + 2] photocycloaddition reactions of naphthoquinone derivatives mediated by chiral oxazaborolidines. We found that the excited-state decomplexation is a key factor in achieving high regio- and enantioselectivities in the photocycloaddition reactions.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Fangmeng Sheng, Bin Wu, Xingya Li, Tingting Xu, Muhammad A. Shehzad, Xiuxia Wang, Liang Ge, Huanting Wang, Tongwen Xu
Summary: Research demonstrates that COF membranes with a channel size of approximately 1.4 nm exhibit efficient ion sieving properties, with high monovalent cation permeation rates and low multivalent cation permeabilities.
ADVANCED MATERIALS
(2021)
Review
Biochemistry & Molecular Biology
Ranita Pal, Pratim Kumar Chattaraj
Summary: This article discusses the bonding between noble gases and noble metals from a quantum chemical perspective. Despite their low reactivity, noble gases can form weak bonds with noble metals such as copper, gold, and silver. Factors such as electronic structure and geometric configuration contribute to this unusual bonding behavior. The study also analyzes the energetics of possible dissociation and internal isomerization channels, as well as the nature of the bond between noble gases and noble metals.
Article
Polymer Science
Ramkrishna Sarkar, Soumabrata Majumdar, Sierd Kuil, Jorg Mallens, Joost J. B. van Der Tol, Rint P. Sijbesma, Johan P. A. Heuts, Anja R. A. Palmans
Summary: Dynamic covalent networks (DCNs) utilize chemical bonds that can break and reform to allow for network reconfiguration under appropriate processing conditions. The addition of the acylsemicarbazide (ASC) motif, capable of hydrogen bonding and dynamic bond exchange, has expanded the repertoire of dynamic covalent bonds. This study demonstrates that the sulfur congener, thioacylsemicarbazide (TASC), also functions as a dynamic covalent bond, albeit with a slower exchange rate than ASC. DCNs based on siloxane incorporating ASC, TASC, or both, exhibit tunable relaxation dynamics that decrease with a higher proportion of TASC motifs. The reduction in stress relaxation is accompanied by a decrease in network creep, and can be controlled by adjusting the ASC/TASC ratio. These networks can be easily processed and dissolved using compression molding and excess hydrazide treatment, respectively. The ability to manipulate network properties and creep in dynamic covalent polymeric networks through minor modifications in dynamic bond structure provides a versatile synthetic approach that can be applied within a wide temperature range.
JOURNAL OF POLYMER SCIENCE
(2023)
Article
Biochemical Research Methods
Xueqin Wei, Jiecheng Ji, Yongxin Nie, Liangjian Tang, Ming Rao, Xiaoqian Wang, Wanhua Wu, Dan Su, Zhihui Zhong, Cheng Yang
Summary: Photochemical methods are increasingly used in organic synthesis, with supramolecular strategies playing a promising role in controlling stereochemistry in chiral photoreactions.
Cyclodextrin derivatives are widely applied chiral hosts for mediating photoreactions, leading to enhanced enantioselectivity.
The protocol for chiral photoreactions includes preparation of derivatives, host-guest inclusion behavior studies, operation of the photoreaction, and chiral HPLC analyses, resulting in excellent regio- and enantioselectivities.
Article
Chemistry, Multidisciplinary
Yi Zeng, Yuexin Zhao, Linhao Yang, Yang Jiang
Summary: Two alternative mechanisms involving non-covalent catalysis by hydrogen-bonding (Path I) and covalent catalysis via hydroxamic acid formation (Path II) are considered for the transamidation of acetamide and benzylamine. Our computational results demonstrate that Path II via O-path is the more favorable pathway.
Article
Chemistry, Multidisciplinary
Kamal K. Ray, Gonzalo Campillo-Alvarado, Hugo Morales-Rojas, Herbert Hopfl, Leonard R. MacGillivray, Alexei V. Tivanski
CRYSTAL GROWTH & DESIGN
(2020)
Article
Chemistry, Multidisciplinary
Jay Quentin, Leonard R. MacGillivray
CRYSTAL GROWTH & DESIGN
(2020)
Article
Chemistry, Multidisciplinary
Gonzalo Campillo-Alvarado, Rachel J. Liu, Daniel W. Davies, Ying Diao
Summary: This study demonstrates the use of perfluorophenyl embraces and boron coordination to enhance dichroism in single crystals of asymmetric azo chromophores. The alignment of molecular transition dipole moments in the supramolecular helices leads to increased dichroism compared to pure 4PAzP, as confirmed by polarized optical microscopy. This novel supramolecular strategy offers a promising approach to enhance dichroism in single-crystalline materials.
CRYSTAL GROWTH & DESIGN
(2021)
Article
Chemistry, Multidisciplinary
Christopher J. Hartwick, Shweta P. Yelgaonkar, Eric W. Reinheimer, Gonzalo Campillo-Alvarado, Leonard R. MacGillivray
Summary: Self-assembled complexes utilizing the ditopic dative bond acceptor 1,3-diboronic acid with catechol and complementary U-shaped donors generate discrete two-component structures with plug-in-socket geometries, supporting solvent inclusion and potentially serving as a basis for designing complex B-based structures.
CRYSTAL GROWTH & DESIGN
(2021)
Article
Chemistry, Physical
Gonzalo Campillo-Alvarado, Michael Bernhardt, Daniel W. Davies, Julio A. N. T. Soares, Toby J. Woods, Ying Diao
Summary: This study demonstrates the successful control of pi-stacking modes and photophysical properties of the anthracene-based organic semiconductor BP4VA through isosteric cocrystallization with 2,4,6-trihalophenols. The presence of 3X-ph-OH during cocrystallization effectively modulates the photoluminescence and molecular frontier orbital energy levels of BP4VA. The results suggest that cocrystallization with minimal changes in coformers can provide convenient access to structural and property diversification for advanced single-crystal electronics.
JOURNAL OF CHEMICAL PHYSICS
(2021)
Article
Chemistry, Multidisciplinary
Eva Cecilia Vargas-Olvera, Frank Jose Salas-Sanchez, Abraham Colin-Molina, Salvador Perez-Estrada, Braulio Rodriguez-Molina, Jose Alejandre, Gonzalo Campillo-Alvarado, Leonard R. MacGillivray, Herbert Hopfl
Summary: This study examined the dynamics of three guests (benzene, naphthalene, and xylene) included in isostructural cavities. The results showed that benzene is highly mobile with fast in-plane jumps, while naphthalene experiences 180-degree jumps at high temperatures. Xylene can only undergo 120-degree in-plane jumps at temperatures close to decomposition due to the methyl groups acting as effective stoppers.
CRYSTAL GROWTH & DESIGN
(2022)
Article
Biochemistry & Molecular Biology
Jay Quentin, Eric W. Reinheimer, Leonard R. MacGillivray
Summary: The ditopic halogen-bond donors 1,2-, 1,3-, and 1,4-diiodotetrafluorobenzene (1,2-, 1,3-, and 1,4-di-I-tFb) form binary cocrystals with the unsymmetrical ditopic X-bond acceptor trans-1-(2-pyridyl)-2-(4-pyridyl)ethylene (2,4-bpe). For (1,2-di-I-tFb).(2,4-bpe) and (1,3-di-I-tFb).(2,4-bpe), the X-bond donor supports the C=C bonds of 2,4-bpe to undergo a topochemical [2+2] photodimerization in the solid state.
Article
Chemistry, Multidisciplinary
Maria Guadalupe Vasquez-Rios, Gonzalo Campillo-Alvarado, Dale C. Swenson, Herbert Hopfl, Leonard R. MacGillivray
Summary: Cocrystallizations of diboronic acids and bipyridines generated hydrogen-bonded cocrystals with different dimensions, where some molecules underwent chemical reactions, forming frameworks with various hydrogen-bonded interactions.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Review
Chemistry, Multidisciplinary
Azzaya Khasbaatar, Zhuang Xu, Jong-Hoon Lee, Gonzalo Campillo-Alvarado, Changhyun Hwang, Brandon N. Onusaitis, Ying Diao
Summary: The assembly of conjugated organic molecules from solution to solid-state is crucial for determining the characteristics of thin films in organic electronics and photovoltaics. Various intermolecular interactions result in distinct aggregate structures, which greatly affect charge transport in solid-state. The assembly of neat materials in blend systems, including phase separation and crystallization, governs the morphology of blend films. This review focuses on molecular assembly processes in conjugated polymers and small molecule acceptors, as well as their impact on thin film morphology and optoelectronic properties. It also discusses the fundamentals of phase transition in blend systems relevant to organic solar cells and how assembly and processing conditions affect blend morphology and device performance.
Article
Chemistry, Multidisciplinary
Maria Guadalupe Vasquez-Rios, Gonzalo Campillo-Alvarado, Leonard R. MacGillivray
Summary: A photoactive cocrystal was obtained through mechanochemistry by coexisting (B)O-H...N hydrogen bonds and B <- N coordination. Specifically, the grinding of a boronic acid and an alkene using a ball mill and liquid-assisted grinding resulted in mixtures of hydrogen-bonded and coordinated complexes similar to those obtained in solution. The alkenes in the hydrogen-bonded assembly undergo a [2+2] photodimerization reaction, reflecting the self-assembly processes. Our findings demonstrate that noncovalent bonds under mechanochemical conditions can contribute to the formation of functional solids, with the weaker hydrogen bonding interactions dominating in this case.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Chemistry, Multidisciplinary
Wegood M. Awad, Daniel W. Davies, Daichi Kitagawa, Jad Mahmoud Halabi, Marieh B. Al-Handawi, Ibrahim Tahir, Fei Tong, Gonzalo Campillo-Alvarado, Alexander G. Shtukenberg, Tamador Alkhidir, Yuki Hagiwara, Mubarak Almehairbi, Linfeng Lan, Shodai Hasebe, Durga Prasad Karothu, Sharmarke Mohamed, Hideko Koshima, Seiya Kobatake, Ying Diao, Rajadurai Chandrasekar, Hongyu Zhang, Changquan Calvin Sun, Christopher Bardeen, Rabih O. Al-Kaysi, Bart Kahr, Pance Naumov
Summary: Molecular crystals have diverse physical properties and can be studied by responding to electric, magnetic, and light fields. The mechanical properties of molecular crystals enhance our understanding of weakly bound molecules under internal and external forces. The importance of mechanical properties to practical applications and the need for improvement in measurement techniques and conceptual tools are emphasized.
CHEMICAL SOCIETY REVIEWS
(2023)
Article
Chemistry, Multidisciplinary
Changan Li, Gonzalo Campillo-Alvarado, Dale C. Swenson, Leonard R. MacGillivray
Summary: By utilizing hydrogen bonds and cation⋯π interactions, a cascade-like [2 + 2] photodimerization of 4-stilbazole in a salt cocrystal is achieved with high yield. The single-crystal X-ray data provides insights into the movements during the photodimerization process in the salt cocrystal.
Article
Chemistry, Organic
Gonzalo Campillo-Alvarado, Leonard R. MacGillivray
Summary: This research highlights the opportunities to direct chemical reactivity in the organic solid state using organoboron molecules, focusing on achieving [2+2]-photocycloadditions in crystalline solids through hydrogen bonding of boronic acids and boron coordination in boronic esters. Organoboron molecules act as templates to organize alkenes for regio- and stereoselective reactions, and future developments in boron in materials and solid-state chemistry are discussed.
Article
Chemistry, Multidisciplinary
Gonzalo Campillo-Alvarado, Elizabeth A. Keene, Dale C. Swenson, Leonard R. MacGillivray
