Review
Chemistry, Inorganic & Nuclear
Vincenzo Balzani, Paola Ceroni, Alberto Credi, Margherita Venturi
Summary: [Ru(bpy)(3)](2+) and its related compounds are a unique family of clever molecules that can process optical and electrical signals, and perform a variety of interesting functions as components of chemical species.
COORDINATION CHEMISTRY REVIEWS
(2021)
Review
Chemistry, Inorganic & Nuclear
Federico Nicoli, Erica Paltrinieri, Marina Tranfic Bakic, Massimo Baroncini, Serena Silvi, Alberto Credi
Summary: Living systems rely on ions and molecules for information processing and motion control. Artificial mimics of biomolecular systems have been developed, and their combination can produce logic-controlled nanomachines with great potential for applications. These systems may lead to the development of 'molecular robots' capable of executing specific functions based on environmental stimuli.
COORDINATION CHEMISTRY REVIEWS
(2021)
Review
Chemistry, Inorganic & Nuclear
Joakim Andreasson, Uwe Pischel
Summary: This review discusses the use of light in addressing stimuli-responsive molecular and supramolecular systems, focusing on molecular photoswitches. Light provides advantages in terms of spatiotemporal control and remote triggering, allowing for precise design of excited state processes for desired logic operations or functions. Photons as traceless reagents enable the recycling and reconfiguration of devices, merging photoswitching with information processing.
COORDINATION CHEMISTRY REVIEWS
(2021)
Article
Biochemical Research Methods
Paula Novo, Marcos D. Garcia, Carlos Peinador, Elena Pazos
Summary: Many cellular processes in living organisms are regulated by complex regulatory networks involving relatively few proteins that switch between different assemblies to perform their functions. This study demonstrates that the conjugation of a specific scaffold to a transcription factor can control its dimerization through a supramolecular complex, allowing for reversible binding to DNA target in response to external stimuli.
BIOCONJUGATE CHEMISTRY
(2021)
Article
Chemistry, Organic
Yang Jiao, J. Fraser Stoddart
Summary: This Perspective summarizes the recent progress in electron/hole catalysis and highlights the methods for injecting or removing electrons in various fields including chemistry, electrochemistry, photochemistry, and mechanochemistry. Additionally, the applications of electron/hole catalysis in molecular switches and supramolecular assemblies are emphasized.
Article
Chemistry, Multidisciplinary
Daniel Hugenbusch, Marc Lehr, Jan-Simon von Glasenapp, Anna J. McConnell, Rainer Herges
Summary: We report the photo-switching properties of two regioisomeric diazocine ligands. The self-assembly of these ligands with Co-II ions was studied, and reversible transformation between different ligand configurations and Co-II complexes was achieved through light-controlled switching.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Esther Nieland, Jona Voss, Andreas Mix, Bernd M. Schmidt
Summary: This study demonstrates the use of visible light to shift dynamic covalent imine assemblies out of equilibrium. A fluorinated azobenzene building block was combined with different amines to create a library of imine macrocycles. The chiral amine provides access to a rich network of macrocycles that undergo isomerisation and interconversion between different species.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Physical
Cai-Cai Zhang, Yang Liu, Zhao-Ying Li, Li-Juan Xing, Xin Zhang, He-Lue Sun, Ke Xu, Jian-Wen Li, Hai-Tao Yu
Summary: Photoswitchable gel-sol systems have been developed using azobenzene derivatives as organic gelators, offering reversible gel-sol transition and tunable fluorescence intensity.
APPLIED SURFACE SCIENCE
(2022)
Article
Chemistry, Multidisciplinary
Andre Seco, Shilin Yu, Arnaud Tron, Nathan D. McClenaghan, Fernando Pina, A. Jorge Parola, Nuno Basilio
Summary: A linear double pyridinium-terminated thread with a central chalcone moiety provides two independent binding sites for cucurbit[7]uril macrocycles in water. The association leads to [2] and [3] pseudorotaxanes, which are pH and photosensitive, with enhanced association upon switching to the cationic flavylium form. Threading the flavylium moiety into CB7 results in a significant increase in fluorescence quantum yield.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Review
Chemistry, Multidisciplinary
Esther Nieland, Jona Voss, Bernd M. Schmidt
Summary: The utilization of light for manipulation and control of supramolecular assemblies is a promising approach in the development of complex, programmable, or multifunctional systems and nanoscopic machine-like entities.
Article
Biophysics
Shuai Cao, Le Zhou, Chang Liu, Huacheng Zhang, Yuxin Zhao, Yanli Zhao
Summary: The ingenious design and synthesis of novel macrocycles brought renewed vigor to supramolecular chemistry in the past decade. Pillarene and pillararene-based functional materials have seen rapid growth in electrochemical studies due to their unique structures and physiochemical properties. Challenges and future developments in this field have been discussed, providing a solid foundation for further bioelectrochemical applications of pillararene systems.
BIOSENSORS & BIOELECTRONICS
(2021)
Article
Chemistry, Multidisciplinary
Hao Hu, Hua Wang, Yuchong Yang, Jiang-Fei Xu, Xi Zhang
Summary: In this study, a cationic porphyrin derivative TMPyP was developed that could be used for specific bacteria-responsive antimicrobial treatment through adaptable photodynamic/photothermal therapy processes. The results showed that TMPyP exhibited strong antimicrobial activity (>99%) through photothermal therapy in hypoxic environments where facultative anaerobes with a strong reducing ability, such as E. coli and S. typhimurium, could reduce TMPyP to phlorin. In aerobic environments with aerobic bacteria, TMPyP functioned as a typical photosensitizer that effectively killed bacteria (>99.9%) through photodynamic therapy. The biocompatibility of TMPyP was significantly improved by forming a host-guest complex with cucurbit[7]uril. This bacteria-responsive porphyrin demonstrates specificity and adaptability in antimicrobial treatment and holds potential in non-invasive treatments of bacterial infections.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Miriam Colaco, Patricia Maximo, A. Jorge Parola, Nuno Basilio
Summary: The study focuses on the kinetics of a water-soluble host-guest system based on cucurbit[8]uril and two DTE photoswitches, demonstrating a method to control the binding kinetics in supramolecular systems using external stimuli. By modifying the structure of the DTE guest molecule, it is possible to significantly slow down the formation/dissociation rates of pseudorotaxane structures, leading to the emergence of a competitive metastable product with important impact on the overall binding kinetics. Additionally, the dissociation kinetics of the host-guest system can be controlled by approximately 100-fold by switching between closed and open DTE isomers.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Diane K. Smith
Summary: Hydrogen bonds play a significant role in organic electrode reactions by stabilizing charged intermediates and products, and facilitating proton-coupled electron transfer. The strength of hydrogen bonds can be altered via electron transfer, and recent research has shown that hydrogen bonds can facilitate reversible electron and proton transfer.
Article
Chemistry, Multidisciplinary
Weiquan Xu, Jin-Yu Chao, Bohan Tang, Zhan-Ting Li, Jiang-Fei Xu, Xi Zhang
Summary: A supramolecular organic framework-type photocatalyst named TM-SOF was constructed. It exhibited improved stability and performance for the photocatalytic oxidation of aryl boronic acids and thioethers.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Organic
Federica Cester Bonati, Andrea Secchi, Gianpiero Cera
Summary: Calixarenes are fascinating macrocycles with diverse applications in supramolecular chemistry. Larger calix[6] and calix[8] are ideal platforms for constructing efficient organometallic catalysts. This review provides an overview of recent advancements in this field, including CAC and C-H bond formations, as well as important inorganic transformations.
TETRAHEDRON LETTERS
(2022)
Article
Chemistry, Multidisciplinary
Giulio Ragazzon, Marco Malferrari, Arturo Arduini, Andrea Secchi, Stefania Rapino, Serena Silvi, Alberto Credi
Summary: The ability to autonomously harness electrical energy in nanosystems can lead to technological opportunities, and the threading and dethreading motions of a self-assembling system powered by current flow can achieve higher energy efficiency compared to other autonomous systems.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Biochemistry & Molecular Biology
Federica Cester Bonati, Margherita Bazzoni, Caterina Baccini, Valeria Zanichelli, Guido Orlandini, Arturo Arduini, Gianpiero Cera, Andrea Secchi
Summary: This work studies the ability of several bis-viologen axles to thread heteroditopic tris(N-phenylureido)calix[6]arene wheels, resulting in interwoven supramolecular complexes. The unidirectionality of the threading process allows the formation of highly preorganized pseudorotaxane and rotaxane species. These compounds possess the correct spatial arrangement, potentially leading to the realization of upper-to-upper molecular capsules based on calix[6]arene derivatives.
Article
Chemistry, Organic
Silvia Cattani, Andrea Secchi, Lutz Ackermann, Gianpiero Cera
Summary: Iron-catalysed C-H alkylations with alkenes on benzamides were achieved using N-triazole assistance. The regioselectivity can switch from linear to branched depending on the nature of the olefin. This approach allows for the synthesis of a variety of decorated benzamides with high levels of chemo-, regio-, and site-selectivity.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Leonardo Andreoni, Giovanni Mariano Beneventi, Gabriele Giovanardi, Gianpiero Cera, Alberto Credi, Arturo Arduini, Andrea Secchi, Serena Silvi
Summary: We synthesized and characterized a dansyl calix[6]arene derivative and its pseudorotaxane complex, and found that it has remarkable complexation ability. The dansyl moieties in the derivative can signal the state of the system through fluorescence, be reversibly protonated to modulate the complexation abilities, and participate in photoinduced electron transfer processes to tune the stability of the complex.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Damian E. Yerien, Jessica Groppi, Al Postigo, Alberto Credi, Romina S. Conde, Massimo Baroncini, Sebastian Barata-Vallejo
Summary: Modified crown ethers are essential in supramolecular chemistry, and have applications in various fields such as phase transfer catalysis, metal extraction, smart materials, and molecular machines. In this study, a one-pot highly selective photocatalytic fluoroalkylation protocol was developed for the mono-functionalization of benzo substituted crown ethers. With broad applicability and high yield, this method allows for the late-stage functionalization of various aromatic crown ethers, including those involved in mechanically interlocked molecules.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Stefano Corra, Massimiliano Curcio, Alberto Credi
Summary: Accurate control of long-range motion at the molecular scale is crucial for energy storage and bionanotechnology. Recent developments have focused on directional operation of man-made molecular motors away from thermal equilibrium. This paper provides a critical assessment of light-driven artificial molecular motors, discussing design criteria and future advances in this research area.
Article
Chemistry, Organic
Gabriele Giovanardi, Gabriele Scarica, Valentina Pirovano, Andrea Secchi, Gianpiero Cera
Summary: We report the first example of gold(I)-catalyzed intramolecular hydroarylation of alkynes for the direct synthesis of inherently chiral calix[4]arenes. This efficient and atom-economical method allows for a formal meta-functionalization of the calix[4]arene macrocycle, leading to the synthesis of a wide range of N-heterocyclic, chiral compounds with high yields and functional group tolerance.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Leonardo Andreoni, Federica Cester Bonati, Jessica Groppi, Davide Balestri, Gianpiero Cera, Alberto Credi, Andrea Secchi, Serena Silvi
Summary: We synthesized and characterized [2]rotaxanes based on a stilbazolium dye and a calix[6]arene macrocycle. Due to the non-symmetry of both components, two orientational isomers were obtained. The two isomers exhibited distinct photophysical and photochemical properties in solution and solid state, surpassing the unencapsulated dye.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Nina Bukhtiiarova, Alberto Credi, Stefano Corra
Summary: In this study, we designed a rotaxane molecular shuttle that can precisely tune the distribution of the ring among two weak recognition sites by changing solvent polarity or the nature of counteranions. The shuttling of the ring can also be toggled by acid-base stimuli, providing a paradigmatic approach for sensing environmental changes and transducing them into a coconformational response.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Nina Bukhtiiarova, Alberto Credi, Stefano Corra
Summary: This is a rotaxane molecular shuttle that uses triazolium and tertiary ammonium units as weak recognition sites for the ring. The distribution of the ring among the two sites can be precisely tuned by changing the solvent polarity or the nature of the counteranions, and the shuttling of the ring between the two stations can be toggled by acid-base stimuli.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Fuying Zhu, Yamei Lin
Summary: In this study, a low-metal iron-supported catalyst (Fe20/NC-Mg) was reported for the efficient synthesis of quinoxaline compounds, using water as a solvent and without additional bases. The synergistic effect of FeNx site and Mg (OH)2 nanorods in the catalyst played a key role in achieving high yields (82-91%) in 16 examples. The gram-level synthesis and reusability of the catalysts after four cycles demonstrated its industrial application potential.
Article
Chemistry, Organic
Mikhail Kozlov, Alexey Tyurin, Andrey Dmitrenok, Vyacheslav Rusak, Aleksander Fedorov, Igor Zavarzin, Yulia Volkova
Summary: This study presents a novel and practical synthesis method for phosphorus-substituted 1,3,4-thiadiazolines using phosphorylthioformic acid hydrazides and ketones. The protocol demonstrates operational simplicity, availability of reagents, and tolerance towards different functional groups.
Article
Chemistry, Organic
Jisna Jose, Thomas Mathew
Summary: 2-Cyclopentenone and its derivatives are highly esteemed synthetic intermediates with exceptional utility in organic synthesis. They are favored structural motifs in numerous pharmaceutical drugs and natural products, highlighting their significance. The review discusses the various methods used to synthesize cyclopentenones from 2016 to 2023.
