Article
Nanoscience & Nanotechnology
Tyus J. Yeingst, Julien H. Arrizabalaga, Ferdousi S. Rawnaque, Lindsay P. Stone, Amar Yeware, Angelica M. Helton, Aman Dhawan, Julianna C. Simon, Daniel J. Hayes
Summary: This study developed an ultrasound-responsive polymer system that can degrade on demand when exposed to high-intensity focused ultrasound (HIFU). Diels-Alder cycloadducts were used to crosslink polycaprolactone (PCL) polymers and underwent a retro Diels-Alder reaction under HIFU stimulation. The relationship between reverse reaction energy barriers and polymer degradation rates was evaluated for two Diels-Alder polymer compositions. HIFU exposure time and amplitude were found to correlate with an increase in PCL degradation for Diels-Alder-based polymers. The study demonstrated that HIFU is an effective image-guided stimulus to control the degradation of Diels-Alder-based PCL polymers on-demand.
ACS APPLIED MATERIALS & INTERFACES
(2023)
Article
Chemistry, Physical
Alexander B. Tesler, Stefan Kolle, Lucia H. Prado, Ingo Thievessen, David Boehringer, Matilda Backholm, Bhuvaneshwari Karunakaran, Heikki A. Nurmi, Mika Latikka, Lena Fischer, Shane Stafslien, Zoran M. Cenev, Jaakko V. I. Timonen, Mark Bruns, Anca Mazare, Ulrich Lohbauer, Sannakaisa Virtanen, Ben Fabry, Patrik Schmuki, Robin H. A. Ras, Joanna Aizenberg, Wolfgang H. Goldmann
Summary: This study developed aerophilic titanium alloy surfaces with thermodynamically stabilized plastrons for antifouling applications. The surfaces have long-term stability and effectively reduce adhesion and contamination.
Article
Chemistry, Physical
Luis R. Domingo, Elham Mazarei, Ahmad Seif, Mar Rios-Gutierez, Ehsan Zahedi, Temer S. Ahmadi
Summary: Computational evidence suggests that the reaction between (3)Sigma(-) g-O-2 and spirovinylcyclopropyl oxindole is catalyzed by iodine radicals under dark conditions, leading to the formation of spiro-1,2-dioxolane. The mechanism involves stepwise reactions and the formation of new bonds is characterized by electron distribution in the intermediate state.
JOURNAL OF PHYSICAL CHEMISTRY A
(2021)
Article
Biochemical Research Methods
Umberto M. Battisti, Rocio Garcia-Vazquez, Dennis Svatunek, Barbara Herrmann, Andreas Loeffler, Hannes Mikula, Matthias Manfred Herth
Summary: Tetrazines have wide applications in biomedical field, including pretargeted imaging. In this study, a kinetic investigation on different tetrazine compounds reacting with trans-cyclooctene (TCO) was conducted. The results reveal that the reactivity of tetrazines in different solvents may not correlate well and tetrazines modified in the 2-position of the phenyl substituent show high intrinsic reactivity towards TCO, which is diminished in aqueous systems. These findings enable the prediction of bioorthogonal reactivity and facilitate the development of substituted aryltetrazines for in vivo applications.
BIOCONJUGATE CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Dong Luo, Zi-Jun Yuan, Lin-Jie Ping, Xiao-Wei Zhu, Ji Zheng, Chuang-Wei Zhou, Xian-Chao Zhou, Xiao-Ping Zhou, Dan Li
Summary: Post-synthetic modification is a general and efficient strategy to functionalize metal-organic cages. In this study, a covalent PSM approach was developed to modify PdnL2n metal-organic cages through Diels-Alder cycloaddition. The functionalized cages exhibited improved solubility and displayed concentration-dependent circular dichroism and aggregation-induced emission.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Chemistry, Multidisciplinary
Razvan C. Cioc, Marc Crockatt, Jan C. Waal, Pieter C. A. Bruijnincx
Summary: This article introduces biomass-derived furanic platform molecules as promising building blocks for renewable chemicals and functional materials, and explores the application of Diels-Alder cycloaddition in converting these renewable resources in an efficient way. The importance of understanding the interplay between kinetics and thermodynamics in the cycloaddition reactions is emphasized, and relevant examples and research findings are provided.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Nanoscience & Nanotechnology
Sophia J. Bailey, Friedrich Stricker, Erik Hopkins, Maxwell Z. Wilson, Javier Read de Alaniz
Summary: A new Diels-Alder-based photopatterning platform utilizing irreversible, light-induced decarbonylation and cleavage reactions has been developed. This platform allows spatially controlled cyclopentadiene reactions in polymer networks, enabling potential applications in photopatterning and various material applications.
ACS APPLIED MATERIALS & INTERFACES
(2021)
Article
Chemistry, Organic
Kseniya A. Alekseeva, Maryana A. Nadirova, Vladimir P. Zaytsev, Evgeniya V. Nikitina, Mikhail S. Grigoriev, Anton P. Novikov, Irina A. Kolesnik, Bernhard Mayer, Thomas J. J. Mueller, Fedor I. Zubkov
Summary: Diversely substituted, partially saturated benzo-[f]-isoindole-4-carboxylic acids were synthesized through a new three-component reaction. The reaction showed high regio- and stereoselectivity, resulting in the formation of a chiral center and a diastereoisomer.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Polymer Science
Paul van den Tempel, Francesco Picchioni, Ranjita K. Bose
Summary: This review critically assesses the kinetic behavior of the furan/maleimide Diels-Alder click reaction and explores its application in forming thermoreversible crosslinks in polymer networks. The study finds differences in kinetics from various studies, potentially caused by chemical side groups, mass transfer limitations, and different analysis methods. The review offers a general guide to assess the feasibility of this reaction in real-life products.
MACROMOLECULAR RAPID COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Samuel Lauzon, Lionel Schouwey, Thierry Ollevier
Summary: A chiral ligand was successfully synthesized and its structure and configuration were determined by single-crystal diffraction analysis. The newly synthesized ligand displayed excellent catalytic activity and selectivity in iron-catalyzed asymmetric reactions.
Article
Chemistry, Organic
Ramalingam Boobalan, Rong-Jie Chein
Summary: The emergence of second-generation sulfur-stabilized borenium cations by halophilic Lewis acid SnCl4 results in highly active chiral Lewis acids that are effective catalysts for [4 + 2] cycloaddition, exhibiting excellent enantioselectivity for a variety of substrates and demonstrating good catalytic efficiency.
Article
Chemistry, Applied
Hanbyeol Kim, Jung Rae Kim, Young-Kwon Park, Jeong-Myeong Ha, Jungho Jae
Summary: In this study, metal phosphates were used as catalysts for biomass conversion to produce sustainable aromatics through DielsAlder cycloaddition reactions. The effects of synthesis method, activation method, and P/Ti molar ratio on the structure and acid properties of titanium phosphate catalysts were systematically studied. The mesoporous titanium phosphate catalyst synthesized by hydrothermal method at 180℃ for 12 h followed by ethanol refluxing at 60℃ for 24 h at a molar P/Ti ratio of 1 showed the highest surface area and acid site density.
Article
Chemistry, Multidisciplinary
Guanghao Huang, Cyrille Kouklovsky, Aurelien de la Torre
Summary: The first enantioselective total synthesis of (+)-lucidumone is described, involving key steps such as an enantioselective inverse-electron-demand Diels-Alder cycloaddition and C-O bond formation. The synthesis is scalable and produced over one gram of natural product in one batch.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Multidisciplinary Sciences
Yuwen Wang, Patrick Czabala, Monika Raj
Summary: In this study, the authors report a one-pot multicomponent Furan-Thiol-Amine reaction inspired by enzymes, which can generate stable pyrrole heterocycles independent of diverse functionalities. The reaction has wide applicability, including selective and irreversible labeling of peptides, synthesis of macrocyclic and stapled peptides, selective modification of different proteins with varying payloads, and labeling of lysine and cysteine in a complex human proteome.
NATURE COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Nicole Houszka, Hannes Mikula, Dennis Svatunek
Summary: 1,2,4,5-Tetrazines are widely used in bioorthogonal chemistry for their high reactivity in Diels-Alder reactions. The substituents in the 3- and 6-positions of the tetrazine scaffold significantly affect the rate of cycloadditions, but this is not explained by frontier molecular orbital interactions. Instead, the high reactivity of mono-substituted tetrazines is due to decreased Pauli repulsion, leading to a more asynchronous approach and reduced distortion energy. Additionally, ethylene is not a good model compound for other alkenes in Diels-Alder reactions.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
William Laure, David Fournier, Patrice Woisel, Joel Lyskawa
Article
Chemistry, Multidisciplinary
Talitha F. Stefanello, Benoit Couturaud, Anna Szarpak-Jankowska, David Fournier, Benoit Louage, Francielle P. Garcia, Celso V. Nakamura, Bruno G. De Geest, Patrice Woisel, Boudewijn van der Sanden, Rachel Auzely-Velty
Article
Polymer Science
Couturaud Benoit, Stefanello Talitha, Fournier David, Sliwa Michel, Szarpack-Jankowska Anna, Auzely-Velty Rachel, Woisel Patrice
Article
Chemistry, Physical
Matthieu Fumagalli, Khaled Belal, Hui Guo, Francois Stoffelbach, Graeme Cooke, Alba Marcellan, Patrice Woisel, Dominique Hourdet
Article
Chemistry, Multidisciplinary
William Laure, Kevin De Bruycker, Pieter Espeel, David Fournier, Patrice Woisel, Filip E. Du Prez, Joel Lyskawa
Article
Polymer Science
Bastian Ebeling, Khaled Belal, Francois Stoffelbach, Patrice Woisel, Muriel Lansalot, Franck D'Agosto
MACROMOLECULAR RAPID COMMUNICATIONS
(2019)
Article
Chemistry, Multidisciplinary
Hui Guo, Dominique Hourdet, Alba Marcellan, Francois Stoffelbach, Joel Lyskawa, Lieselot de Smet, Aurelien Vebr, Richard Hoogenboom, Patrice Woisel
CHEMISTRY-A EUROPEAN JOURNAL
(2020)
Article
Chemistry, Multidisciplinary
Pauline Salaun, Alexandre Fadel, Mario Pelaez-Fernandez, Bahae-Eddine Mouloud, Jean-Francois Tahon, Christophe Volkringer, Ahmed Addad, Patrice Woisel, Gaelle Le Fer
Summary: This study reports the first example of hybrid COF-polymer particles, in which polymers are used to manipulate the growth of 2D COF nanostructures. The study investigates how the nature and molar mass of the polymer influence the shaping of hybrid particles, and different polymers result in different particle structures.
Article
Materials Science, Multidisciplinary
Aprimedam Viktor Joo, Jonathan Potier, Nouzha Ouhssou, Barbara Pepino Mendes, Gaelle Le Fer, Patrice Woisel, Kedafi Belkhir
Summary: In this study, hydrophobic self-immolative polymer (SIP) segments were combined with hydrophilic polyethylene glycol (PEG) to form diblock and triblock amphiphilic copolymers. The designed architectures showed complete cleavage of the triggering units in the SIP segments under UV irradiation, and the depolymerization rates of the SIP backbones were up to 60%. Self-assemblies prepared from the diblock copolymers exhibited rapid disintegration under UV light and the ability to encapsulate and release hydrophobic model molecules on demand.
ACS APPLIED POLYMER MATERIALS
(2023)
Article
Chemistry, Multidisciplinary
Solenne Ritaine, Valentin Ternel, Patrice Woisel, Jerome P. Claverie, Jonathan Potier
Summary: To address VOCs pollution, researchers developed high performance thermosets using Pillar[5]arenes, which can absorb chlorine and bromide-based VOCs. The thermosets were synthesized by modifying poly(2-vinyl-4,4-dimethylazlactone) with mono-amino substituted P[5]A followed by crosslinking with isophore diamine. The results showed that the P[5]A-based thermosets efficiently absorbed carcinogenic VOCs, and the efficiency depended on the affinity of the cavities for the VOCs, indicating selectivity towards certain VOCs.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Materials Science, Multidisciplinary
Lieselot De Smet, Khaled Belal, Aurelien Vebr, Joel Lyskawa, Francois Stoffelbach, Richard Hoogenboom, Patrice Woisel
Summary: In this study, a supramolecular approach was developed to create a smart polymeric hydrogel that can measure temperature and the duration of heat exposure. The hydrogel utilizes a double memory principle based on kinetic control of the dissociation of host-guest complexes within a thermoresponsive polymer hydrogel. By determining the reswelling capability of the hydrogel, the heating temperature and time can be determined.
ACS MATERIALS LETTERS
(2023)
Article
Polymer Science
Erigene Bakangura, David Fournier, Fanny Coumes, Patrice Woisel, Daniel Grande, Benjamin Le Droumaguet
Summary: Functional nanoporous polymeric materials were prepared from novel PS-b-PEO diblock copolymer precursors containing reversible boronate ester junction. The generation of oriented cylindrical nanopores was achieved by selective etching of PEO under mild acidic conditions.
Article
Polymer Science
Hui Guo, Gaelle Le Fer, Thi Nga Tran, Aurelie Malfait, Dominique Hourdet, Alba Marcellan, Francois Stoffelbach, Joel Lyskawa, Richard Hoogenboom, Patrice Woisel
Summary: The combination of thermo-responsive polymers with supramolecular chemistry has led to the development of adaptive materials based on reversible regulation of host-guest complexation. The study found that the phase separation mechanism of thermoresponsive polymers is a key factor that dominates the host-guest complexation behavior.
Article
Polymer Science
Florine Nonque, Audrey Sahut, Nicolas Jacquel, Rene Saint-Loup, Patrice Woisel, Jonathan Potier
Article
Chemistry, Multidisciplinary
Zhanyao Hou, Wim Dehaen, Joel Lyskawa, Patrice Woisel, Richard Hoogenboom
CHEMICAL COMMUNICATIONS
(2017)
