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Stereoelectronic Effect of Protecting Groups on the Stability of Galactosyl Donor Intermediates.
Molecules
January 2025
Department of Chemistry, Hunter College, The City University of New York, 695 Park Ave., New York, NY 10065, USA.
Using methods of DFT, we investigated the effect of electron withdrawing and electron donating groups on the relative stability of tentative glycosyl donor reaction intermediates. The calculation shows that by changing the stereoelectronic properties of the protecting group, we can influence the stability of the dioxolenium type of intermediates by up to 10 kcal mol, and that by increasing nucleophillicity of the 4--Bz group, the dioxolenium intermediate becomes more stable than a triflate-donor pair. We exploited this mechanism to design galactosyl donors with custom protecting groups on O2 and O4, and investigated the outcome of the reaction with cyclohexanol.
View Article and Find Full Text PDFPhotoluminescent Properties of Tb-UiO-66 Metal-Organic Framework Analogues.
Inorg Chem
January 2025
Department of Chemistry and Biochemistry and Centre for NanoScience Research, Concordia University, 7141 Sherbrooke Street West, Montreal, Quebec H4B 1R6, Canada.
Three new analogues of Tb-UiO-66 with various functional groups (-F, -Br, -NH) on the terephthalic acid linker of the metal-organic framework (MOF) are synthesized and characterized. The photoluminescent properties of these analogues, as well as Tb-UiO-66 and Tb-UiO-66-(OH), are studied and correlated to the calculated energies for the triplet (T) states of each linker. The results show that the addition of electron withdrawing groups, such as -F and -Br, lead to higher T energies, resulting in quantum yields in the range of 6-31%.
View Article and Find Full Text PDFMolecular Design, Synthesis and Anti-cancer Activity of Novel Pyrazolo[3,4-b]pyridine-based Glycohybrid Molecules.
Bioorg Chem
January 2025
Department of Chemistry, Institute of Science, Banaras Hindu University, Varanasi 221005, India; Glycochemistry Laboratory, School of Physical Sciences, Jawaharlal Nehru University, New Delhi 110067, India. Electronic address:
Molecular hybridization is an emerging strategy in medicinal chemistry for designing new bioactive molecules that link pharmacophores covalently and shows synergistic enhanced properties. Herein, we have developed pyrazolo[3,4-b]pyridine-based new glycohybrids considering the Warburg effect. A microwave-assisted, copper-catalyzed efficient synthesis of new triazole-linked glycohybrids based on pyrazolo[3,4-b]pyridines scaffold was achieved successfully in high yields with inherent stereochemical diversity from d-glucose, d-galactose, and d-mannose.
View Article and Find Full Text PDFNHC-Based Deep-Red Phosphorescent Iridium Complexes Featuring Three-Charge (0, -1, -2) Ligands.
Inorg Chem
January 2025
School of Environmental and Chemical Engineering, Jiangsu University of Science and Technology, Zhenjiang 212003, P. R. China.
N-heterocyclic carbene (NHC)-based phosphorescent iridium complexes have attracted extensive attention due to their good optical properties and high stability in recent years. However, currently reported NHC-based iridium complexes can easily achieve emission of blue, green, or even ultraviolet light, while emission of red or deep-red light is relatively rare. Here, we report a new family of NHC-based deep-red iridium complexes (Ir1, Ir2, Ir3, and Ir4) featuring three-charge (0, -1, -2) ligands.
View Article and Find Full Text PDFThe elimination of the A' unit from -type Y6-derivatives has led to the development of a new class of -benzodipyrrole (-BDP)-based A-DBD-A-type NFAs. In this work, two new A-DBD-A-type NFAs, denoted as CFB and CMB, are designed and synthesized, where electron-withdrawing fluorine atoms and electron-donating methyl groups are substituted on the benzene ring of the -BDP moiety, respectively. CFB exhibits a blue-shifted absorption spectrum, stronger intermolecular interactions, shorter π-π stacking distances, and more ordered 3D intermolecular packing in the neat and blend films, enabling it to effectively suppress charge recombination in the PM6:CFB device showing a higher PCE of 16.
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