Article
Chemistry, Applied
Fabienne Hoffmann-Emery, Katrin Niedermann, Pankaj D. Rege, Manuel Konrath, Christian Lautz, Anne Katrin Kraft, Carine Steiner, Fritz Bliss, Andre Hell, Rolf Fischer, Diane E. Carrera, Danial Beaudry, Remy Angelaud, Sushant Malhotra, Francis Gosselin
Summary: A sustainable second-generation process for GDC-0134 was developed to meet the safety and greenness requirements of supplying pivotal clinical studies. The process involved the discovery of alternative solvents and improved reaction conditions, resulting in a significant reduction in process mass intensity and the successful production of a large amount of GDC-0134.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2022)
Article
Polymer Science
Naoki Shida, Kazuyuki Ninomiya, Natsuki Takigawa, Keiichi Imato, Yousuke Ooyama, Ikuyoshi Tomita, Shinsuke Inagi
Summary: A postpolymerization nucleophilic aromatic substitution reaction is used to efficiently diversify conjugated polymers, with complete substitution achieved by thiophenol derivatives and carbazole, while disubstitution occurs with para-selectivity by phenol derivatives.
Article
Chemistry, Multidisciplinary
Zhensheng You, Kosuke Higashida, Tomohiro Iwai, Masaya Sawamura
Summary: In this study, non-activated aryl fluorides were found to react with potassium diorganophosphinites through nucleophilic aromatic substitution to form tertiary phosphine oxides, with a mechanism involving nucleophile-dependent SNAr reaction pathways.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Correction
Chemistry, Multidisciplinary
Kun-Xu Teng, Li-Ya Niu, Yan-Fei Kang, Qing-Zheng Yang
Summary: This study discusses a rational design of a dual lock-and-key supramolecular photosensitizer based on aromatic nucleophilic substitution for specific and enhanced photodynamic therapy.
Article
Chemistry, Multidisciplinary
Eduardo Rodrigo, Rainer Wiechert, Magnus W. Walter, Wilfried Braje, Herve Geneste
Summary: By using KOH, the direct F to OH exchange of aromatic and heteroaromatic substrates can be achieved under mechanochemical conditions, making the process more atom economical and environmentally friendly compared to other methods.
Article
Chemistry, Organic
Karlis-Eriks Krikis, Irina Novosjolova, Anatoly Mishnev, Maris Turks
Summary: A new method utilizing 1,2,3-triazoles as leaving groups in SNAr-Arbuzov reactions to transform C-N bonds into C-P bonds was developed. C6-phosphonated 2-triazolylpurine derivatives were synthesized for the first time with yields reaching up to 82% in the C-P-bond-forming event. The regioselectivity pattern of C6-position being more reactive towards substitution in the SNAr-Arbuzov reaction of 2,6-bistriazolylpurines was conclusively proven through X-ray analysis.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Chemistry, Organic
Harry C. Sample, Mathias O. Senge
Summary: The study details the SNAr reactions of seven types of porphyrinoids with different pyrrole units, analyzing the substitution dependent on the type of nucleophile and the site of substitution. Nucleophilic substitution on porphyrinoids is found to be an cost-effective procedure with the ability to yield complex substituent patterns, regardless of the type of porphyrinoid.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Yunzhi Lin, Hang Shi
Summary: Aromatic organosilicon compounds are valuable synthetic materials due to their diverse reactivities and compatibility with various functional groups. However, (trialkylsilyl)arenes are considered unsuitable substrates for transition-metal-catalyzed cross-coupling reactions due to low polarity and steric hindrance. This study presents a rhodium-catalyzed addition method for (trialkylsilyl)arenes and electrophiles, and reveals an unexpected stepwise pathway for fluoride-induced desilylation through computational studies.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Review
Biochemistry & Molecular Biology
Ritesh Gautam, Ian Geniza, Scott T. Iacono, Chadron M. Friesen, Abby R. Jennings
Summary: Perfluoropyridine (PFPy) is a highly reactive organofluorine compound that has versatile applications, including chemical synthesis, fluoropolymers, and fluorinated network materials.
Article
Chemistry, Multidisciplinary
Jie Zhang, Zuowei Xie
Summary: This study reported a pyridine-enabled transition-metal-free regioselective nucleophilic aromatic cage B(4)-H amination reaction, offering a selective amination strategy for o- and m-carboranes. Control experiments indicated the crucial role of magnesium complex, bidentate ligand, and reaction temperature in the process of cage isomerization.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Clayton P. Donald, Amy Boylan, Truong N. Nguyen, Po-An Chen, Jeremy A. May
Summary: The (IPr)GaCl3/AgSbF6, AgSbF6, and GaCl3 catalysts were found to efficiently catalyze the substitution of the hydroxyl group of secondary and tertiary propargylic alcohols with organoboronic acids via C-C bond formation, and GaCl3 catalyst effectively synthesized all-carbon quaternary propargylic centers. These catalysts demonstrated the ability to perform substitutions at carbons bearing alkyl substituents, a capability that was lacking in other systems. The study showed that highly hindered carbon stereocenters, including quaternary centers bearing doubly ortho-substituted aryl rings, could be accessed efficiently using this method.
Article
Chemistry, Multidisciplinary
Junu Kim, Yusuke Hayashi, Sara Badr, Kazuya Okamoto, Toshikazu Hakogi, Haruo Furukawa, Satoshi Yoshikawa, Hayao Nakanishi, Hirokazu Sugiyama
Summary: Extensive kinetic studies were conducted to identify new reaction pathways and evaluate their feasibility in resolving contradictions in the understanding of amination reaction via nucleophilic aromatic substitution. The use of different bases in the reaction system resulted in distinct concentration profiles, including sigmoidal profiles in both starting material and product. These profiles suggests that a species acting as a catalyst evolves during the reaction, indicating that the reaction mechanism changes depending on the specific base. The study presents novel identification of reaction conditions and additives that induce mechanism changes, while elucidating the catalytic effect of a newly discovered species formed during the reaction, thereby resolving the previously conflicting explanations of the reaction pathways.
REACTION CHEMISTRY & ENGINEERING
(2023)
Article
Chemistry, Multidisciplinary
Guangyu Zhang, Jiaxi Xu
Summary: In this study, a new cascade reaction involving the nucleophilic substitution, O[1,3] sigmatropic shift, Smiles rearrangement, and amide and ester exchange reaction was observed. It resulted in the synthesis of 2-((2/4-nitroaryl)amino)aryl carboxylate derivatives from 2/4-nitroaryl halides and N-acyl-N-arylhydroxylamines in the presence of sodium hydride in THF. This reaction provides a novel strategy for the synthesis of 2-hydroxydiarylamine derivatives under transition metal-free conditions.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Organic
Dmitry A. Vasilenko, Sevastian E. Dronov, Yuri K. Grishin, Elena B. Averina
Summary: The synthesis of hybrid isoxazole-triazole molecules is of great interest due to their significant applications in pharmaceutical chemistry. This study presents an efficient method for synthesizing 5-azidoisoxazoles through a chemoselective nitro-group substitution reaction. The resulting 5-azidoisoxazoles can be used in CuACC-reaction to synthesize biologically relevant 5-(1,2,3-triazol-1-yl)isoxazoles, with both reactions achieving excellent yields and functional group tolerance under mild conditions.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Engineering, Environmental
Kyunggu Kim, Junsik Kang, Hochun Lee
Summary: The hybrid thermoelectrochemical and concentration cell (i-TCC) based on carbonate solvents outperforms current n-type TECs, showing high Seebeck coefficient, figure of merit, and Carnot efficiency at temperatures above 40 degrees Celsius. It provides a new perspective in harvesting low-grade waste heat.
CHEMICAL ENGINEERING JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Laura Parejo, Mahdi Chaari, Sara Santiago, Gonzalo Guirado, Francesc Teixidor, Rosario Nunez, Jordi Hernando
Summary: Icosahedral metallacarboranes are unique molecules with two icosahedra sharing a metal center vertex. Among them, the anionic cobalt-based metallacarborane displays oxidation-reduction processes through outer sphere electron transfer. Tethering this molecule to a dye results in switchable luminescent molecules, which act as electrochemically-controlled fluorescent molecular switches in solution and have the ability to form gels through self-assembly. The interplay between dye pi-stacking and metallacarborane interactions governs the supramolecular arrangement, with one compound maintaining luminescent behavior in the gel state.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Acoustics
Amparo Ferrer-Vilanova, Yasmine Alonso, Jiri Dietvorst, Marta Perez-Montero, Rosalia Rodriguez-Rodriguez, Kristina Ivanova, Tzanko Tzanov, Nuria Vigues, Jordi Mas, Gonzalo Guirado, Xavier Munoz-Berbel
Summary: This technology utilizes sonochemical coating to create robust blue-colored textiles with bacterial sensing capability, enabling on-site detection of live bacteria. The textiles are sensitive to both Gram-positive and Gram-negative bacteria, recover their original blue color through oxidation-reduction reactions, and can be applied to various materials for controlling and preventing microbial infections in hospitals, industries, schools, and homes.
ULTRASONICS SONOCHEMISTRY
(2021)
Article
Biophysics
Sara Santiago-Malagon, Diego Rio-Colin, Haniyeh Azizkhani, Miguel Aller-Pellitero, Gonzalo Guirado, F. Javier del Campo
Summary: This study describes the construction of a self-powered electrochromic device for the determination of metabolites in sweat, which can be visualized by the naked eye. By utilizing screen-printing technology, the device is able to simplify the complexity of skin-patch wearable sensors, potentially leading to a powerful analytical tool without the need for external detection systems.
BIOSENSORS & BIOELECTRONICS
(2021)
Article
Chemistry, Analytical
Maryam Bayat, Hossein Izadan, Sara Santiago, Francesc Estrany, Mohammad Dinari, Dariush Semnani, Carlos Aleman, Gonzalo Guirado
Summary: In this study, three dye molecules and SDS were used as dopant agents for the electrochemical synthesis of PPy layers. The combination of dye molecules and SDS showed excellent synergistic effect on the electrochemical stability and optical properties of the layers, resulting in improved electrochromic parameters. The research suggests that increasing the number of anion groups in dye molecules and decreasing their dimensions as dopant agents may enhance the electrochemical and electrochromic properties of the resultant layer.
JOURNAL OF ELECTROANALYTICAL CHEMISTRY
(2021)
Article
Chemistry, Organic
Marc Villabona, Sandra Wiedbrauk, Florian Feist, Gonzalo Guirado, Jordi Hernando, Christopher Barner-Kowollik
Summary: By utilizing UV and visible light illumination, control of two-color light can be used to regulate covalent ligation, enabling precise manipulation within materials.
Article
Electrochemistry
Silvia Mena, Cyril Loault, Veronica Mesa, Iluminada Gallardo, Gonzalo Guirado
Summary: In this study, a new simple molecule was synthesized for controlling and tuning CO2 reactivity based on electrode potential. The compound showed different reaction processes in inert atmosphere and CO2 atmosphere, opening up new possibilities for manipulating reaction processes associated with CO2.
Article
Chemistry, Analytical
Jiri Dietvorst, Amparo Ferrer-Vilanova, Sharath Narayana Iyengar, Aman Russom, Nuria Vigues, Jordi Mas, Lluisa Vilaplana, Maria-Pilar Marco, Gonzalo Guirado, Xavier Munoz-Berbel
Summary: This study introduces a cyanotype-based photochemical amplification reaction for detecting low bacterial concentrations efficiently and simply, which is expected to have a significant impact on clinical diagnosis of infectious diseases.
ANALYTICAL CHEMISTRY
(2022)
Article
Electrochemistry
Sara Santiago, Clara Richart, Silvia Mena, Iluminada Gallardo, Jordi Hernando, Gonzalo Guirado
Summary: This manuscript discusses the use of carbon capture and utilization to synthesize high-added chemicals using CO2. The study reveals that carboxylated spiropyran derivatives can be synthesized with high yields and conversion rates through an electrocarboxylation process using a silver cathode and polar aprotic solvents. This research provides a new sustainable strategy for designing and building smart surfaces with switchable physical properties.
Article
Biotechnology & Applied Microbiology
Naroa Uria-Molto, Ruben D. Costa, Cybeles Nunziata, Sara Santiago, Gonzalo Guirado, Xavier Munoz-Berbel, Lukasz Kowalski
Summary: The study aims to develop a compact, portable, and self-sustaining format of energy production based on Microbial Fuel Cell (MFC) technologies. By assembling and comparing three different MFC configurations, it was found that the hybrid-MFC performed the best, with sustained operation for over a month, making it suitable for long-term power supply of low-power electronic devices in the field.
ELECTRONIC JOURNAL OF BIOTECHNOLOGY
(2022)
Article
Chemistry, Analytical
Carolina Gasco, Luis Rodriguez-Santiago, Mariona Sodupe, Rosa Maria Sebastian, Gonzalo Guirado
Summary: This paper proposes a new electroinduced approach to increase the crosslinking density of electroactive polybenzoxazines by designing new monomers and investigating the electrochemical reactions of polybenzoxazines in solution or ionogel matrices. These studies lay the foundations for the design of smart polybenzoxazines that can undergo dual-cure mechanisms at low electrochemical potential values.
MICROCHEMICAL JOURNAL
(2022)
Article
Chemistry, Analytical
Sara Santiago, Hugo Cruz, Noemi Jordao, Pablo Gimenez-Gomez, Karolina Zalewska, Xavier Munoz-Berbel, Andreia F. M. Santos, Jordi Hernando, Luis C. Branco, Gonzalo Guirado
Summary: This study establishes the photoelectrochromic properties of four diarylethene ionic liquids (DAE-ILs) and demonstrates their potential applications in smart ionogels for photoelectrochemical devices.
MICROCHEMICAL JOURNAL
(2022)
Article
Chemistry, Physical
Alison N. Roth, Jemima Opare-Addo, Eunbyeol Gi, Silvia Mena, Gonzalo Guirado, Richard D. Schaller, Emily A. Smith, Javier Vela
Summary: Mixed-metal chalcohalide semiconductors, specifically Pb2SbS2I3 and Pb2BiS2I3, were synthesized in solution phase using readily available precursors. The reaction parameters were fine-tuned to produce rod-like structures with tunable dimensions. The quaternary chalcohalides exhibited photoluminescence both as an ensemble and at the single particle level, as observed through fluorescence microscopy. Electronic structure calculations were used to evaluate the stability and band gap of Pb2SbS2I3 polymorphs and their coloring patterns. These synthetic methods pave the way for further exploration of complex chalcohalides and other multinary semiconductors for new technological applications.
CHEMISTRY OF MATERIALS
(2023)
Article
Chemistry, Multidisciplinary
Arnau Marco, Gonzalo Guirado, Rosa Maria Sebastian, Jordi Hernando
Summary: This study develops optical chemosensors for CO2 by preparing hydrogels functionalized with spiropyrans, which exhibit acidochromic properties and undergo color changes upon exposure to CO2.
FRONTIERS IN CHEMISTRY
(2023)
Article
Biophysics
Joan Aymerich, Amparo Ferrer-Vilanova, Jose Cisneros-Fernandez, Roger Escude-Pujol, Gonzalo Guirado, Lluis Teres, Michele Dei, Xavier Munoz-Berbel, Francisco Serra- Graells
Summary: Early detection of low bacterial concentrations is crucial for minimizing healthcare and safety issues. In this study, a potentiostatic-amperometric Delta-Sigma modulator with the ability to cancel flicker noise and improve the limit of detection was developed. The integrated circuit, with an area of 2.3 mm2, was attached to an inkjet-printed electrochemical sensor. The disposable device was capable of detecting live bacterial concentrations as low as 102 CFU/mL within an hour.
BIOSENSORS & BIOELECTRONICS
(2023)
Article
Multidisciplinary Sciences
S. Mena, N. Karkour, V. Alaphilippe, J. P. Botero, M. Jimenez, D. Linget, L. Gibelin, V. Le Ven, A. Marquet, S. Mellouh, E. Josson, W. Benassou, X. Munoz-Berbel, G. Guirado, C. Guardiola
Summary: This work presents the validation of a new OptoElectro-Mechanical system for two-dimensional dose evaluation using radiochromic films. The results show that the proposed system is feasible and provides similar results to the standard method. Further developments are being conducted to improve the spatial resolution and real-time performance of the system for better clinical application of radiochromic films.
SCIENTIFIC REPORTS
(2023)
