An efficient three component reaction with enaminones, primary amines and aldehydes resulted in easy access to 1,4-dihydropyridines with different substituents at the 1-, 3-, 4- and 5-positions. Microwaves improved the reaction yield, reducing also considerably the reaction time and the amount of solvent used. Chiral primary amines gave chiral 1-substituted-1,4-dihydropyridines. The 4-(1-naphthyl) and 4-(phenanthren-9-yl)dihydropyridine derivatives exhibited an interesting photoluminescence behavior, which suggests their potential application as suitable photoinduced intramolecular electron-transfer systems.
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http://dx.doi.org/10.3762/bjoc.8.50 | DOI Listing |
Org Lett
January 2025
School of Pharmacy, Yantai University, Yantai 264005, P. R. China.
Compared with the energetically favorable 5- or 6-membered fluoro-functionalized heterocycles, the construction of medium-sized fluoro-heterocycles is relatively under-researched because of their inherently unfavorable enthalpic and entropic nature. Based on rational design and DFT calculations, a novel photocatalytic difluoromethyl radical-initiated intramolecular 7--trig cyclization was realized, thus affording a sustainable route for the synthesis of challenging fluoro-functionalized medium-sized -heterocycles. Depending on atomic dipole moment corrected Hirshfeld population (ADCH) charge calculations, the chemoselective 6--trig radical cyclizations were further replenished.
View Article and Find Full Text PDFDalton Trans
January 2025
Institute of Chemistry, Faculty of Science and Technology, University of Silesia, Szkolna 9, 40-006 Katowice, Poland.
Over the last five decades, diimine rhenium(I) tricarbonyl complexes have been extensively investigated due to their remarkable and widely tuned photophysical properties. These systems are regarded as attractive targets for design functional luminescent materials and performing fundamental studies of photoinduced processes in transition metal complexes. This review summarizes the latest developments concerning Re(I) tricarbonyl complexes bearing donor-acceptor (D-A) and donor-π-acceptor (D-π-A) ligands.
View Article and Find Full Text PDFJ Colloid Interface Sci
January 2025
College of Chemistry, Soochow University, Suzhou 215123, PR China. Electronic address:
In the manipulation of π-conjugated organic polymer, strategic alterations to the polymerization cascade facilitate the integration of donor (D) and acceptor (A) entities within the polymer's backbone. Such control is instrumental in broadening the photoresponse spectrum, enhancing photoinduced charge separation, and augmenting the efficiency of charge transfer processes. The oxygen-containing amino group (-ONH) was innovatively grafted into the polymerization process of the triazine-heptazine ring skeleton, and the -ONH was used as a capping agent to change the chain bonding in the polymerization process, thus a new intramolecular D-A structure was successfully constructed.
View Article and Find Full Text PDFChemistry
December 2024
School of Chemical and Biopharmaceutical Sciences, Technological University Dublin, City Campus, Grangegorman, Dublin 7, Ireland.
Donor-acceptor BODIPY dyads, functionalized at the 2 and 6 positions with benzyl ester (BDP-DE) or carboxylic acid (BDP-DA) groups, were synthesized, and their optoelectronic properties were investigated. Carbonyl groups were found to increase the reduction potential of the BODIPY core by 0.15-0.
View Article and Find Full Text PDFSmall
December 2024
Department of Chemistry, Indian Institute of Technology, Kharagpur, West Bengal, 721302, India.
Anticipating intramolecular excited-state proton-coupled electron transfer (PCET) process within dinuclear Ir-photocatalytic system via the covalent linkage is seminal, yet challenging. Indeed, the development of various dinuclear complexes is also promising for studying integral photophysics and facilitating applications in catalysis or biology. Herein, this study reports dinuclear [Ir(bis{imidazo-phenanthrolin-2-yl}-hydroquinone)(ppy)] (1) complex by leveraging both ligand-centered redox property and intramolecular H-bonding for exploring dual excited-state proton-transfer assisted PCET process.
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