IOCB covers 2022

The picture depicts the functional group tolerance in the conversion of aldehydes into secondary or tertiary amines via reduction of the intermediate imines with Cl3SiH, catalyzed by DMF. (Cover art: Tomáš Belloň / IOCB Prague)

• Article: Matouš, P.; Májek, M.; Kysilka, O.; Kuneš, J.; Maříková, J.; Růžička, A.; Pour, M.; Kočovský, P. Reaction Outcome Critically Dependent on the Method of Workup: An Example from the Synthesis of 1-Isoquinolones. J. Org. Chem. 2021, 86, 8078–8088. https://doi.org/10.1021/acs.joc.1c00561
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The cover art demonstrates the importance of proper computational methodology for predicting the structure of multicomponent solids that may exist as salts or cocrystals. An approach based on classical mechanics (represented by Newton's laws) favors salts, and an approach that includes quantum effects (hydrogen atom delocalization) predicts cocrystals. (Cover art: Tomáš Belloň / IOCB Prague)

• Article: Štoček, J. R.; Socha, O.; Císařová, I.; Slanina, T.; Dračínský, M. Importance of Nuclear Quantum Effects for Molecular Cocrystals with Short Hydrogen Bonds. J. Am. Chem. Soc. 2022, 144, 16, 7111–7116. https://doi.org/10.1021/jacs.1c10885 
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Tissue-transparent red light is used to release oleic acid, a signaling lipid, into cells, which induces Ca2+ oscillations accompanied by a turn-on fluorescence response. In their Communication (e202205855), Tomáš Slanina and co-workers show that π-extended BODIPY photocages substituted with sulfonate groups can selectively target inner or outer membranes and release carboxylic acid upon red-light illumination. (Cover art: Tomáš Belloň / IOCB Prague)

• Article: Poryvai, A.; Galkin, M.; Shvadchak, V.; Slanina, T. Red-Shifted Water-Soluble BODIPY Photocages for Visualisation and Controllable Cellular Delivery of Signaling Lipids. Angew. Chem. Int. Ed. 2022, e202205855. https://doi.org/10.1002/anie.202205855 
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Abstraction of an optimal control solid-state NMR experiment. A powdered sample is spun inside a solenoidal coil. The coil delivers sophisticated radio-frequency pulses (gold numbers fed into coil wires) to manipulate the magnetization vector. Transferring both vector components between nuclei allows systematic sensitivity gains in multidimensional NMR spectra of solids. (Cover art: Tomáš Belloň / IOCB Prague)

• Article: Blahut, J.; Brandl, M. J.; Pradhan, T.; Reif, B.; Tošner, Z. Sensitivity-Enhanced Multidimensional Solid-State NMR Spectroscopy by Optimal-Control-Based Transverse Mixing Sequences. J. Am. Chem. Soc. 2022, 144, 17336–17340. https://doi.org/10.1021/jacs.2c06568
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Cover art: Tomáš Belloň / IOCB Prague

• Article: Sakamoto, D.; Gay Sánchez, I.; Rybáček, J.; Vacek, J.; Bednárová, L.; Pazderková, M.; Pohl, R.; Císařová, I.; Stará, I. G.; Starý, I. Cycloiridated Helicenes as Chiral Catalysts in the Asymmetric Transfer Hydrogenation of Imines. ACS Catal. 2022, 12, 10793–10800. https://doi.org/10.1021/acscatal.2c01816 
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Cover art: Tomáš Belloň / IOCB Prague

• Article: Choutka, J.; Kratochvíl, M.; Císařová, I.; Pohl, R.; Kaminský, J.; Parkan, K. Silicon-bridged (1→1)-disaccharides: an umpoled glycomimetic scaffold. Org. Biomol. Chem. 2022, 20, 7613–7621. https://doi.org/10.1039/D2OB01161A 
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Crystal City in a chiral world: The Crystal City is illuminated by chiral suns shining left-circularly polarized light (L-CPL) or right-circularly polarized light (R-CPL). The light of the two suns interacts with the skyscraper crystals differently revealing differences in their inner crystal structure. (Cover art: Tomáš Belloň / IOCB Prague)

• Article: Krupová, M.; Leszczenko, P.; Sierka, E.; Emma Hamplová, S.; Pelc, R.; Andrushchenko, V. Vibrational Circular Dichroism Unravels Supramolecular Chirality and Hydration Polymorphism of Nucleoside Crystals. Chem. Eur. J. 2022, 28, e202201922. https://doi.org/10.1002/chem.202201922
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Thermoresponsive polymers have found many promising (bio)medical applications, e.g. in situ thermogelling with controlled drug-release, polymer-supported brachytherapy, immunotherapy, and wound dressing. Despite the benefits of thermoresponsive polymers, their biodistribution and fate remained largely unknown, hindering their clinical use. Herein, Ondřej Groborz, Richard Hoogenboom, Martin Hrubý, and co-workers elucidate the pharmacokinetics and fate of thermoresponsive polymers in mice, in article 2201344. Finally, they perform a property-to-pharmacokinetics analysis. (Cover art: Tomáš Belloň / IOCB Prague)

• Article: Groborz, O., Kolouchová, K., Pankrác, J., Keša, P., Kadlec, J., Krunclová, T., Pierzynová, A., Šrámek, J., Hovořáková, M., Dalecká, L., Pavlíková, Z., Matouš, P., Páral, P., Loukotová, L., Švec, P., Beneš, H., Štěpánek, L., Dunlop, D., Melo, C. V., Šefc, L., Slanina, T., Beneš, J., Van Vlierberghe, S., Hoogenboom, R., Hrubý, M. Pharmacokinetics of Intramuscularly Administered Thermoresponsive Polymers. Adv. Healthcare Mater. 2022, 11, 2201344. https://doi.org/10.1002/adhm.202201344 
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The molecular bending was identified as an important factor that has a profound effect on the self-assembly of originally rod-shaped organic molecules on a (111) gold surface. Combination of various analytical techniques and advanced computations revealed that originally straight molecular rods acquired a characteristic “J-shape” once adsorbed on a metallic surface. (Cover art: Tomáš Belloň / IOCB Prague)

• Article: Rončević, I.; Kaletová, E.; Varga, K.; Císařová, I.; Bastl, Z.; Jiang, J.-C.; Kaleta, J. Molecular Bending: An Important Factor Affecting the Packing of Self-Assembled Monolayers of Triptycene-Based Molecular Rods on a (111) Gold Surface. J. Phys. Chem. C 2022, 126, 7193–7207. https://doi.org/10.1021/acs.jpcc.1c10627