Article
Chemistry, Multidisciplinary
Jonathan Trouve, Paolo Zardi, Shaymaa Al-Shehimy, Thierry Roisnel, Rafael Gramage-Doria
Summary: Utilizing secondary interactions between substrates and catalysts is a promising approach to discover selective transition metal catalysts for atom-economy C-H bond functionalization. The most powerful catalysts are often discovered through trial-and-error screening, as small stereo-electronic modifications within the substrate and catalyst can lead to vastly different reactivities.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Karolis Norvaisa, Sophie Maguire, Claire Donohoe, John E. O'Brien, Brendan Twamley, Ligia C. Gomes-da-Silva, Mathias O. Senge
Summary: Inspired by 'picket-fence' systems, this study utilized strain to introduce intramolecular tension, leading to selective compound atropisomer conversion and the formation of distinctive supramolecular nanostructures.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Karolis Norvaisa, John E. O'Brien, Daire J. Gibbons, Mathias O. Senge
Summary: This study sheds light on the fundamental issue of atropisomerism in porphyrins, using benzenesulfonic acid for host-guest interactions and NMR spectroscopy to characterize all four rotamers. The research suggests that charge-assisted complexation is key to unraveling the atropisomeric enigma in porphyrinoids. Additionally, X-ray structural analysis was used to investigate weak host-guest interactions in nonplanar porphyrins.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Maksym Matviyishyn, Agata Bialonska, Bartosz Szyszko
Summary: Crownphyrins are a class of hybrid macrocycles combining structural features of porphyrin and crown ethers. They possess the ability to bind neutral and ionic guests. The presence of dynamic covalent imine linkages connecting the dipyrrin segment with the ether chain enables unusual coordination behavior of crownphyrins.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Masafumi Okuno, Keita Yamana, Shogo Kawamura, Kotaro Nishimura, Shodai Hino, Riku Kawasaki, Atsushi Ikeda
Summary: Tetrakis(4-aminophenyl)porphyrin and tetrakis(4-acetamidophenyl)porphyrin were dissolved in water using a polysaccharide (λ-carrageenan) as a water-solubilizing agent. The photodynamic activity of the CGN-2 complex was lower than that of the CGN-1 complex, but the selectivity index (SI) of the CGN-2 complex was higher. In vivo experiments showed that the CGN-2 complex inhibited tumor growth with higher blood retention compared to the CGN-1 complex and Photofrin.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Review
Chemistry, Organic
Bartosz Szyszko
Summary: This review discusses recent developments in the field of synthetic chemistry of PAH-porphyrin hybrids, focusing on phenanthrene-embedded carbaporphyrinoids and related systems. The discussion covers various aspects of phenanthriporphyrin chemistry, including its spectroscopic features, aromaticity, core reactivity, and coordination properties. The review also highlights the use of phenanthriporphyrinoids as ligands for organometallic chemistry and for constructing conformational and stereochemical switches. The potential for using related macrocycles as building blocks for carbaporphyrinoid cages is also discussed.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Benedikt Platzer, Beatrice Berionni Berna, Martina Bischetti, Daniel O. Cicero, Roberto Paolesse, Sara Nardis, Tomas Torres, Dirk M. Guldi
Summary: This study investigates the non-covalent interaction between electron-donating corroles and electron-accepting phthalocyanines. It demonstrates that this interaction efficiently leads to the formation of charge-separated states, which in turn influences the light harvesting and charge transfer processes.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Ryou Kubota, Itaru Hamachi
Summary: Living cells are capable of integrating multiple bio-supramolecules to carry out complex physiological functions. Synthetic supramolecular systems that mimic cell-like responses and functions are desired. Recent progress in constructing multicomponent supramolecular soft materials through hybridization of supramolecules with functional molecules is highlighted. These materials exhibit bioinspired responses to stimuli and offer promise for applications in soft robotics, disease diagnosis, and tissue regeneration.
Article
Chemistry, Organic
Karolis Norvaisa, Kathryn Yeow, Brendan Twamley, Marie Roucan, Mathias O. Senge
Summary: This study explores the benefits of combining nonplanar porphyrins with traditional molecular designs to introduce new concepts. Selective demethylation based on less hindered positions, isolation of symmetrical and unsymmetrical porphyrin compounds, and analyzing intramolecular interactions via X-ray crystallography highlight the importance of nonplanar systems in supramolecular ensemble design.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Chong-Bin Tian, Qing-Fu Sun
Summary: Discrete organopalladium coordination cages have great potential in various applications such as molecular recognition and sensing, drug delivery, and enzymatic catalysis. Heteroleptic cages with complex architectures and anisotropic cavities have received increasing attention recently. This concept article discusses a powerful self-assembly strategy for constructing a family of organopalladium cages from a given library of ligands, including both homoleptic and heteroleptic structures. The heteroleptic cages often exhibit fine-tuned structures and emergent properties, distinct from their homoleptic counterparts. The concepts and examples provided in this article offer rational guidance for the design of new coordination cages with advanced functions.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Maksym Matviyishyn, Bartosz Szyszko
Summary: Porphyrin and crown ether hybrids, with elements of a tetrapyrrole macrocycle and an oligo(ethylene glycol) segment, have emerged as promising molecules. These hybrids exhibit excellent ligand and host capabilities, intriguing redox chemistry, interesting optical properties, and reactivity towards transition metals.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Wei-Bao He, Sai-Jie Zhao, Jing-Yang Chen, Jun Jiang, Xiang Chen, Xinhua Xu, Wei-Min He
Summary: A practical method for the synthesis of 4-thiocyanato-1H-pyrazoles was established through an electrochemical cascade reaction of hydrazines, 1,3-diones and NH4SCN under metal-, chemical oxidant- and external electrolyte-free conditions. Importantly, both a gram-scale synthesis of 4-thiocyanato-1H-pyrazoles and five one-pot sequential transformations starting from hydrazine were successfully achieved.
CHINESE CHEMICAL LETTERS
(2023)
Article
Chemistry, Multidisciplinary
Mo Sun, Jie Deng, Andreas Walther
Summary: Nature achieves hierarchical control of biofunctions in complex sensory landscapes through cross-regulation of multiple fuel-driven chemical/enzymatic reaction networks (CRNs/ERNs). We present a simple example of communication and cross-regulation between two fuel-driven DNA-based ERNs using a concatenated RNA transcription regulator. The RNA produced by ERN1 can activate or deactivate DNA in ERN2, establishing communication between the two ERNs. The incorporation of RNase H enables RNA degradation and autonomous recovery of ERN2. We propose that concatenation of multiple CRNs/ERNs can be used to design more elaborate autonomous regulatory mechanisms in systems chemistry and synthetic biology.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Multidisciplinary Sciences
Xiaoping Wang, Mao Quan, Huan Yao, Xin-Yu Pang, Hua Ke, Wei Jiang
Summary: The authors report a pair of water-soluble naphthotubes with a pH-responsive cavity for switchable bifunctional recognition in water. These hosts have a switchable cavity and can be used for the construction of smart self-assembly systems and water-soluble molecular machines.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Andrew. T. Turley, Magnus W. D. Hanson-Heine, Stephen. P. Argent, Yaoyang Hu, Thomas. A. Jones, Michael Fay, Simon Woodward
Summary: Large S-8-corona[n]arene macrocycles with alternating aryl and 1,4-C6F4 subunits were successfully synthesized on large scales using new high acceleration SNAr substitution protocols. The size and functionality of the macrocycles can be adjusted by selecting the appropriate precursor and catalyst. Furthermore, the inclusion of solvent controls the conformation and fluorine-fluorine interactions of the macrocycles, leading to spontaneous self-assembly into honeycomb-like lattices.
Review
Chemistry, Multidisciplinary
Rik R. Tykwinski
ACCOUNTS OF CHEMICAL RESEARCH
(2019)
Article
Chemistry, Multidisciplinary
Constantin Hetzer, Bettina S. Basel, Sebastian M. Kopp, Frank Hampel, Fraser J. White, Timothy Clark, Dirk M. Guldi, Rik R. Tykwinski
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2019)
Article
Chemistry, Multidisciplinary
Miriam Hauschild, Lan Chen, Sebastian H. Etschel, Michael J. Ferguson, Frank Hampel, Marcus Halik, Rik R. Tykwinski
Article
Chemistry, Multidisciplinary
Yueze Gao, Vroni Walter, Michael J. Ferguson, Rik R. Tykwinski
CHEMISTRY-A EUROPEAN JOURNAL
(2020)
Article
Chemistry, Multidisciplinary
David Guzman, Ilias Papadopoulos, Giulia Lavarda, Parisa R. Rami, Rik R. Tykwinski, M. Salome Rodriguez-Morgade, Dirk M. Guldi, Tomas Torres
Summary: The study demonstrates the efficient energy transfer between a subporphyrazine and a pentacene dimer through intramolecular Forster resonance energy transfer and intramolecular singlet fission. The polarity of the solvent plays a crucial role in adjusting spectral overlap, ensuring a significant Forster rate constant, and maximizing triplet quantum yields.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Multidisciplinary Sciences
Johannes Zirzlmeier, Stephen Schrettl, Jan C. Brauer, Emmanuel Contal, Laurent Vannay, Eric Bremond, Eike Jahnke, Dirk M. Guldi, Clemence Corminboeuf, Rik R. Tykwinski, Holger Frauenrath
NATURE COMMUNICATIONS
(2020)
Editorial Material
Chemistry, Physical
Rik R. Tykwinski, Dirk M. Guldi
Article
Chemistry, Multidisciplinary
Thaddeus W. Golbek, Ryan A. Faase, Mette H. Rasmussen, Rik R. Tykwinski, Jeffrey M. Stryker, Simon Ivar Andersen, Joe E. Baio, Tobias Weidner
Summary: Petroleum asphaltenes are surface active compounds found in crude oils, with interactions with surfaces and interfaces impacting reservoir exploitation. This study used functionalized model asphaltenes on SAM surfaces to demonstrate different adsorption behaviors on hydrophobic and hydrophilic surfaces. Understanding pure and fractionated asphaltenes at the molecular level is crucial for predicting their varied surface interactions.
Article
Chemistry, Organic
Matthew A. Johnson, Max M. Martin, Kevin Cocq, Norbert Jux, Michael J. Ferguson, Rik R. Tykwinski
Summary: The Friedel-Crafts acylation of hexaphenylbenzene selectively produces monoacylated products. The resulting ketones are used as precursors for the synthesis of [5]cumulenes, with one of the derivatives exhibiting significant stability due to the presence of a sterically demanding group. The rotational barrier for diethynyl[5]cumulenes is estimated using VT NMR studies.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
David E. Scott, Matthias Schulze, Jeffrey M. Stryker, Rik R. Tykwinski
Summary: Asphaltenes, comprising the heaviest and least understood fraction of crude petroleum, are a diverse and complex mixture of organic and organometallic molecules. Efforts to model asphaltene characteristics and aggregation behavior through synthetic model compounds have started to impact the field, offering opportunities to better understand the characteristics and reactivity of asphaltenes.
CHEMICAL SOCIETY REVIEWS
(2021)
Article
Chemistry, Multidisciplinary
Johannes Zirzlmeier, Giulia Lavarda, Henrik Gotfredsen, Ilias Papadopoulos, Lan Chen, Timothy Clark, Rik R. Tykwinski, Tomas Torres, Dirk M. Guldi
Article
Chemistry, Multidisciplinary
Yueze Gao, Yuxuan Hou, Fernando Gordillo Gamez, Mike J. Ferguson, Juan Casado, Rik R. Tykwinski
Article
Chemistry, Multidisciplinary
Diana-Paola Medina, Ilias Papadopoulos, Giulia Lavarda, Henrik Gotfredsen, Parisa R. Rami, Rik R. Tykwinski, M. Salome Rodriguez-Morgade, Dirk M. Guldi, Tomas Torres
Article
Chemistry, Multidisciplinary
Bettina S. Basel, Ryan M. Young, Matthew D. Krzyaniak, Ilias Papadopoulos, Constantin Hetzer, Yueze Gao, Nathan T. La Porte, Brian T. Phelan, Timothy Clark, Rik R. Tykwinski, Michael R. Wasielewski, Dirk M. Guldi
Article
Chemistry, Multidisciplinary
Bettina Sabine Basel, Constantin Hetzer, Johannes Zirzlmeier, Dominik Thiel, Rebecca Guldi, Frank Hampel, Axel Kahnt, Timothy Clark, Dirk Michael Guldi, Rik R. Tykwinski