Sustainability and Chaos in the Abiotic Polymerization of 3′,5′ Cyclic Guanosine Monophosphate: The Role of Aggregation

Glued by guanines: In this work, we show that the unique aggregation properties of H-form 3′,5′ cyclic guanosine monophosphate molecules enable the sustainable non-enzymatic template-free synthesis of oligonucleotide sequences from nucleotide precursors on timescales of several days even in the presence of water.

[Full Papers]

Dr. Giovanna Costanzo, Dr. Judit E. Šponer, Prof. Jiří Šponer, Dr. Angela Cirigliano, Prof. Piero Benedetti, Dr. Valeria Giliberti, Dr. Raffaella Polito, Prof. Ernesto Di Mauro

doi.org/10.1002/syst.202000011

P- and F-co-doped Carbon Nitride Nanocatalysts for Photocatalytic CO2 Reduction and Thermocatalytic Furanics Synthesis from Sugars

Brown sugar: A new synthetic protocol provides P,F-co-doped mesoporous carbon nitride (PFCN) with high surface area and low band gap. Inspired by its extended visible-light absorption and acid-base bifunctional nature, this new class of catalyst was explored for the photocatalytic reduction of CO2 into methanol and for the thermal catalytic conversion of carbohydrates into high-value furanics compounds.

[Full Papers]

Dr. Subodh Kumar, Prof. Manoj B. Gawande, Josef Kopp, Dr. Stepan Kment, Prof. Rajender S. Varma, Prof. Radek Zbořil

doi.org/10.1002/cssc.202001172

Synthesis and Cytotoxic and Antiviral Activity Profiling of All-Four Isomeric Series of Pyrido-Fused 7-Deazapurine Ribonucleosides

Isomers matter: All four isomeric series of novel 4-substituted pyrido-fused 7-deazapurine ribonucleosides possessing pyridine nitrogen at different positions were designed, synthesized, and tested for cytostatic and antiviral activity. The most active showed submicromolar cytotoxic effects and good selectivity for cancer cells. The mechanism of action was also investigated.

[Full Papers]

Lucia Veselovská, Natálie Kudlová, Dr. Soňa Gurská, Dr. Barbora Lišková, Martina Medvedíková, Dr. Ondřej Hodek, Eva Tloušťová, Nemanja Milisavljevic, Dr. Michal Tichý, Dr. Pavla Perlíková, Dr. Helena Mertlíková-Kaiserová, Jana Trylčová, Dr. Radek Pohl, Dr. Blanka Klepetářová, Dr. Petr Džubák, Prof. Dr. Marián Hajdúch, Prof. Dr. Michal Hocek

doi.org/10.1002/chem.202001124

Di(benzothienyl)cyclobutenes: Toward Strained Photoswitchable Fluorophores

Strained switching: Fluorescent photoswitchable dyes are essential for several super-resolution microscopy techniques. Dyes with enhanced photoswitching performance based on diarylethenes containing sterically constrained perfluorocyclobutene ring have been developed. The mechanism of the reaction of thianaphthenes with hexafluorocyclobutene leading to the target dyes was studied and formed byproducts were characterized. The photoswitching reaction was investigated using both optical and NMR-based methods and quantum yields of photoconversion were measured.

[Full Papers]

Dr. Dmytro Sysoiev, Dr. Eliška Procházková, Dr. Aleksander Semenenko, Dr. Radek Pohl, Prof. Dr. Svitlana Shishkina, Dr. Blanka Klepetářová, Dr. Volodymyr Shvadchak, Dr. Dmytro A. Yushchenko

doi.org/10.1002/cplu.202000481

In situ Near-Ambient Pressure X-ray Photoelectron Spectroscopy Reveals the Influence of Photon Flux and Water on the Stability of Halide Perovskite

Solar cell deactivation: For similar exposures, the soaking of light proves more detrimental to the perovskite film than water vapor. Absorbed photons create Frenkel defects in the perovskite crystal. The number of created Frenkel defects depends strongly on the used illumination. The higher the photon flux, the higher the creation of Frenkel defects, and thus the stronger the degradation of power conversion efficiency and the stronger the hysteresis in the J-V characteristics.

[Full Papers]

Dr. M. Kot, Dr. L. Kegelmann, H. Köbler, Dr. M. Vorokhta, Dr. C. Escudero, Dr. P. Kúš, Dr. B. Šmíd, Dr. M. Tallarida, Prof. S. Albrecht, Prof. A. Abate, Prof. I. Matolínová, Prof. D. Schmeißer, Prof. J. I. Flege

doi.org/10.1002/cssc.202001527

P- and F-co-doped Carbon Nitride Nanocatalysts for Photocatalytic CO2 Reduction and Thermocatalytic Furanics Synthesis from Sugars

The Cover Feature shows a novel synthetic protocol that provides P-, F-co-doped mesoporous carbon nitride (PFCN) with high surface area and lower bandgap. Encouraged by its extended visible light absorption and acid-base bifunctional nature, this new class of catalyst has been explored for the photocatalytic reduction of CO2 into methanol and thermal catalytic conversion of carbohydrates into high-value furanics compounds. More information can be found in the Full Paper by S. Kumar et al.

[Cover Pictures]

Dr. Subodh Kumar, Prof. Manoj B. Gawande, Josef Kopp, Dr. Stepan Kment, Prof. Rajender S. Varma, Prof. Radek Zbořil

doi.org/10.1002/cssc.202002041

Defect-Enhanced CO2 Reduction Catalytic Performance in O-Terminated MXenes

Enhancing catalytic performance through vacancies: Vacancies influence the binding energy of intermediates and further affect the limiting potential of the electrochemical carbon dioxide reduction reaction. The catalytic performance of MXenes can be enhanced by introducing a suitable defect type. Furthermore, the shift of Fermi level can be a simple yet promising descriptor to predict the effect exerted by vacancies.

[Full Papers]

Hetian Chen, Dr. Albertus D. Handoko, Tianshuai Wang, Jiale Qu, Jiewen Xiao, Xiaopeng Liu, Prof. Dominik Legut, Prof. Zhi Wei Seh, Prof. Qianfan Zhang

doi.org/10.1002/cssc.202001624

Cyanine-Flavonol Hybrids for Near-Infrared Light-Activated Delivery of Carbon Monoxide

Carbon monoxide (CO) is an endogenous signaling molecule with a remarkable therapeutic potential hindered by its inherent toxicity. The cross-breeding of a CO-releasing flavonol moiety with a cyanine dye enabled access to the family of CO-releasing molecules activatable upon irradiation with near-infrared light up to 820 nm. These hybrids liberate two molecules of CO with efficiencies surpassing those of the state-of-the-art systems by two orders of magnitude. The biocompatibility and applicability of this system were showcased both in vitro and in vivo. The cover image was created by Lenka Štacková, Peter Štacko, and Orazio Angelo Arcidiacono. More information can be found in the Full Paper by P. Štacko, P. Klán, et al. (DOI: 10.1002/chem.202003272).

[Cover Pictures]

Dr. Lenka Štacková, Marina Russo, Dr. Lucie Muchová, Vojtěch Orel, Prof. Libor Vítek, Dr. Peter Štacko, Prof. Petr Klán

doi.org/10.1002/chem.202004017

Reverse Semi-Combustion Driven by Titanium Dioxide-Ionic Liquid Hybrid Photocatalyst

Hybrid theory: An effective method to prepare TiO2@IL semiconductor-liquid junctions for CO2 photo-conversion is developed. The ionic liquid (IL) plays a dual role by inducing a shift of the valence band with simultaneously decreasing the band gap as well as continuous generation of formate radicals, which suggests a decrease of CO2 activation energy barrier and thus improves the catalyst performance (yield and selectivity to CO).

[Full Papers]

Dr. Muhammad I. Qadir, Dr. Marcileia Zanatta, Jose Pinto, Dr. Isabel Vicente, Dr. Aitor Gual, Dr. Emily F. Smith, Prof. Brenno A. D. Neto, Prof. Paulo E. N. de Souza, Dr. Sherdil Khan, Prof. Jairton Dupont, Dr. Jesum Alves Fernandes

doi.org/10.1002/cssc.202001717

Helquats as Promoters of the Povarov Reaction: Synthesis of 1,2,3,4-Tetrahydroquinoline Scaffolds Catalyzed by Helicene-Viologen Hybrids

“Helquats are structurally linked to helicenes and viologens. Here we explored their application as electron-transfer catalysts for the synthesis of 1,2,3,4 tetrahydroquinolines by the Povarov reaction…” Read more about the story behind the cover in the Cover Profile and about the research itself at 10.1002/cplu.2012000151.

[Cover Profile]

Dr. Paul E. Reyes-Gutiérrez, Dr. Tynchtyk T. Amatov, Dr. Pavel Švec, Dr. Ivana Císařová, Dr. David Šaman, Dr. Radek Pohl, Dr. Filip Teplý, Dr. Lubomír Pospíšil

doi.org/10.1002/cplu.202000552

Cyanine-Flavonol Hybrids for Near-Infrared Light-Activated Delivery of Carbon Monoxide

CO worker: Carbon monoxide (CO) is a signaling molecule with potent therapeutic properties hampered by its inherent toxicity. Here, cross-breeding a CO-releasing flavonol moiety with heptamethine cyanine dye leads to highly efficient transition-metal-free photoCORMs (CO-releasing molecules). These photoCORMs operate in the middle of the phototherapeutic window, release two molecules of CO upon irradiation, and are shown to be applicable in vivo.

[Full Papers]

Dr. Lenka Štacková, Marina Russo, Dr. Lucie Muchová, Vojtěch Orel, Prof. Libor Vítek, Dr. Peter Štacko, Prof. Petr Klán

doi.org/10.1002/chem.202003272

Predicting protein stability and solubility changes upon mutations: data perspective

In silico predictions have become an integral part of successful biocatalyst design. Modern computational analysis for protein engineering applies machine learning to predict changes in protein stability and solubility on introducing mutations. Here we summarize state-of-the-art for the most critical part of the approach: mutational datasets used for training and validation.

[Minireviews]

Dr. Stanislav Mazurenko

doi.org/10.1002/cctc.202000933

A General Synthetic Approach and Photophysical Properties of Regioselectively Fluorinated [5]- and [6]-Helical Bispiroindenofluorenes

Fluorinated helical dispirodihydroindenofluorenes: Fluorinated haloarylcarbaldehydes serve as starting material for rapid 5-step synthesis of selectively fluorinated [n]helical bispirodohydrondeno[2,1-c]fluorenes (n=5, 6). Intramolecular catalytic cyclotrimerization was used to assemble the basic molecular framework. The fluorinated dihydroindenofluorenes had emission fluorescence maxima in the range of 386-413 nm, with quantum yields up to 0.92.

[Full Papers]

Dr. Ilaria Caivano, Dr. Zdeněk Tošner, Ivana Císařová, Dr. David Nečas, Prof. Dr. Martin Kotora

doi.org/10.1002/cplu.202000434

Helquats as Promoters of the Povarov Reaction: Synthesis of 1,2,3,4-Tetrahydroquinoline Scaffolds Catalyzed by Helicene−Viologen Hybrids

The Front Cover shows how helquat molecules (shown as solar panels) can be used as organocatalysts in the Povarov reaction. The background combines historical monuments of Prague and the new research centre of the Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences, while the yellow plants represent alternative fuels. More information can be found in the Full Paper by P. E. Reyes-Gutiérrez, L. Pospíšil, and co-workers.

[Cover Pictures]

Dr. Paul E. Reyes-Gutiérrez, Dr. Tynchtyk T. Amatov, Dr. Pavel Švec, Dr. Ivana Císařová, Dr. David Šaman, Dr. Radek Pohl, Dr. Filip Teplý, Dr. Lubomír Pospíšil

doi.org/10.1002/cplu.202000565

Kinetic and mechanistic study of CO oxidation over nanocomposite Cu−Fe−Al oxide catalysts

Active species in catalyst: Mechanism of CO oxidation over nanocomposite CuFeAl oxide catalyst has been studied by mechanistic approach: combination of catalytic and kinetic measurements and near ambient pressure XPS. We have found that small amount of copper (3-5 wt%) forms the active component - CuO/CuFeOx clusters while increase in copper content leads to decrease of catalytic activity due to formation of low active spinel phase - CuxAlyFe3-x-yO4.

[Full Papers]

Dr. Aleksandr Fedorov, Dr. Andrey Saraev, Anna Kremneva, Aleksandra Selivanova, Dr. Mykhailo Vorokhta, Dr. Bretislav Šmíd, Dr. Olga Bulavchenko, Prof. Vadim Yakovlev, Dr. Vasily Kaichev

doi.org/10.1002/cctc.202000852

Photochemistry of a 9-Dithianyl-Pyronin Derivative: A Cornucopia of Reaction Intermediates Lead to Common Photoproducts

The Cover Feature shows the interrelationships of some of the key intermediates generated upon irradiation of a 9-dithianyl-pyronin derivative with yellow light. This complex photochemical oxidative transformation leads to a 9H-xanthen-9-one derivative, formic acid, and carbon monoxide as the main photoproducts. This work provides insights into the (photo)reactivity of substituted xanthene/pyronin dyes, the photobleaching of which can be a serious obstacle in their applications. More details can be found in the Full Paper by J. Roithová, P. Klán, and co-workers. Graphic designed by Marek Martínek.

[Cover Pictures]

Dr. Marek Martínek, Dr. Jiří Váňa, Dr. Peter Šebej, Dr. Rafael Navrátil, Dr. Tomáš Slanina, Dr. Lucie Ludvíková, Prof. Jana Roithová, Prof. Petr Klán

doi.org/10.1002/cplu.202000587

Turning Donepezil into a Multi-Target-Directed Ligand through a Merging Strategy

Strike! Starting from a proposed drug combination of idebenone and donepezil, we rationally designed and synthesized a small library of highly merged donepezil-based multi-target-directed ligands (MTDLs), obtained by indanone bioisosteric substitution. The new MTDL 9 has been shown to hit Alzheimer's disease by cholinesterase inhibition, together with Aβ and oxidative pathway modulation.

[Full Papers]

Dr. Rosaria Perone, Claudia Albertini, Dr. Elisa Uliassi, Flaminia Di Pietri, Pedro de Sena Murteira Pinheiro, Dr. Sabrina Petralla, Nicola Rizzardi, Prof. Romana Fato, Dr. Lenka Pulkrabkova, Dr. Ondrej Soukup, Dr. Anna Tramarin, Prof. Manuela Bartolini, Prof. Maria Laura Bolognesi

doi.org/10.1002/cmdc.202000484

Electron-Withdrawing Substituted Quinazoline Push-Pull Chromophores: Synthesis, Electrochemical, Photophysical and Second-Order Nonlinear Optical Properties

4-Cyanoquinazoline, 2-(4-cyanophenyl)quinazoline and 2-(4-trifluorophenyl)quinazoline chromophores bearing 5-(4-aminophenyl)thiophen-2-yl or 4-aminophenyl electron-donor (D) units have been synthesized. Data of UV/Vis and emission spectroscopy, cyclic voltammetry, electric field induced second harmonic generation (EFISH) method and quantum-chemical calculations for all compounds have been analyzed.

[Full Papers]

Tatiana N. Moshkina, Dr. Pascal Le Poul, Dr. Alberto Barsella, Prof. Oldřich Pytela, Prof. Filip Bureš, Prof. Françoise Robin-Le Guen, Dr. Sylvain Achelle, Prof. Emiliya V. Nosova, Prof. Galina N. Lipunova, Prof. Valery N. Charushin

doi.org/10.1002/ejoc.202000870

Advances in Organic Anode Materials for Na-/K-Ion Rechargeable Batteries

Sustainable electrodes: Sodium-ion and potassium-ion batteries are likely to contribute significantly in the upcoming years to global energy security. Sustainable electrode materials must be developed to enable this growth. Organic molecules are at the core of this technology and materials offering low-voltage redox are improving. This Minireview tracks the progress and remaining challenges in this domain.

[Minireviews]

Dr. Aamod V. Desai, Prof. Russell E. Morris, Dr. A. Robert Armstrong

doi.org/10.1002/cssc.202001334

Transition-Metal-Mediated versus Tetrazine-Triggered Bioorthogonal Release Reactions: Direct Comparison and Combinations Thereof

Direct comparison: Two different metal-promoted as well as the tetrazine-triggered bioorthogonal cleavage reactions were investigated with the goal to directly compare the release yield, reaction rates and efficiency of the transformations under identical experimental conditions. In addition, this study shows that some of these reactions are mutually orthogonal, which opens up the possibility to perform simultaneous multiple decaging experiments.

[Communications]

Francesca Mancuso, Michal Rahm, Dr. Rastislav Dzijak, Dr. Helena Mertlíková-Kaiserová, Dr. Milan Vrabel

doi.org/10.1002/cplu.202000477

Photochemistry of a 9-Dithianyl-Pyronin Derivative: A Cornucopia of Reaction Intermediates Lead to Common Photoproducts

A hunt for intermediates: The photochemistry of a 9-dithianyl-pyronin derivative, which undergoes an oxidative transformation at the meso-position to give a 3,6-diamino-9H-xanthen-9-one derivative, formic acid, and carbon monoxide as the main photoproducts, is presented. The identification of many intermediates and their interrelationships is presented and was used to provide a complete picture of the transformation that brings new inputs to a rational design of new photoactivatable pyronin or xanthene derivatives.

[Full Papers]

Dr. Marek Martínek, Dr. Jiří Váňa, Dr. Peter Šebej, Dr. Rafael Navrátil, Dr. Tomáš Slanina, Dr. Lucie Ludvíková, Prof. Jana Roithová, Prof. Petr Klán

doi.org/10.1002/cplu.202000370

Bovine Serum Albumin Catalysed Hydrogen and Deuterium Evolution at Mercury Electrodes

The stronger deuteron bond than that of a proton 1) contributed to less effective transport of deuterons mediated by protein bovine serum albumin (BSA) at the Hg|D2O interface and 2) enhanced structural stability of the surface-attached deuteronated native BSA in D2O solution (BSA−D) where its transition current (Istr1/2) was less intense than that of the protonated BSA in H2O solution (BSA−H).

[Full Papers]

Dr. Vlastimil Dorčák, Dr. Hana Černocká, Prof. Emil Paleček

doi.org/10.1002/cplu.202000348

SQM/COSMO Scoring Function: Reliable Quantum-Mechanical Tool for Sampling and Ranking in Structure-Based Drug Design

Scoring functions on tour: The minireview covers a challenging journey of a semiempirical QM-based scoring function (SQM/COSMO SF) toward its successful application in structure-based drug design. On the way, the SQM/COSMO SF has acquired sampling and ranking powers, giving promise for library enrichment. It has proven its superiority over conventional SFs in a dozen of protein targets and is thus ready for new challenges, e. g. a large-scale testing of diverse data sets.

[Minireviews]

Dr. Adam Pecina, Saltuk M. Eyrilmez, Dr. Cemal Köprülüoğlu, Dr. Vijay Madhav Miriyala, Dr. Martin Lepšík, Dr. Jindřich Fanfrlík, Dr. Jan Řezáč, Prof. Pavel Hobza

doi.org/10.1002/cplu.202000120

Helquats as Promoters of the Povarov Reaction: Synthesis of 1,2,3,4-Tetrahydroquinoline Scaffolds Catalyzed by Helicene-Viologen Hybrids

Helquats in action: Helquats (HQs), compounds structurally linked to helicenes and viologens, are used for the first time as organocatalysts. The HQ-catalyzed Povarov reaction between an N-Arylimine and different olefins gave us the possibility to achieve the synthesis of 1,2,3,4-Tetrahydroquinolines in good yields and in moderate diastereoselectivities. Mechanistic studies revealed that helquats act as single-electron transfer oxidants through a cation-radical mechanism.

[Full Papers]

Dr. Paul E. Reyes-Gutiérrez, Dr. Tynchtyk T. Amatov, Dr. Pavel Švec, Dr. Ivana Císařová, Dr. David Šaman, Dr. Radek Pohl, Dr. Filip Teplý, Dr. Dr. Lubomír Pospíšil

doi.org/10.1002/cplu.202000151