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The Unusual Mesophases and Properties Exhibited by a Family of Glycosteroids.
Chemistry
January 2025
Universite Claude Bernard Lyon 1, ICBMS, Bâtiment Lederer, 1 Rue Victor Grignard, F-69622, Villeurbanne, FRANCE.
In this article we describe research on the synthesis and characterization of a family of "Janus" amphiphiles composed of disaccharide head groups and alkaloid units joined together via a methylene linker, and bearing a lateral aliphatic chain of varying length. The condensed phases formed by self-organization of the products as a function of temperature were characterized by differential scanning calorimetry, thermal polarized light microscopy, and small angle X-ray scattering, allied with computational modelling and simulations. Structural studies on heating specimens from the solid showed that some homologues exhibited lamellar, columnar and bicontinuous mesophases, whereas the same homologues revealed different phase sequences on cooling from the amorphous liquid.
View Article and Find Full Text PDFAn intrinsic goal when designing synthetic methodology is to identify approaches whereby readily accessible precursors are converted into an array of products, which efficiently tap into new 3D-chemical space. In these studies, readily available bicyclic lactam-bromolactones have been interrogated in several fragment growth protocols by utilizing the halogen and lactone motifs as versatile linchpins for strategic construction of C-C, C-N, C-O, and C-S bonds. Diastereospecific C(sp)-C(sp) Kumada coupling of sterically imposing [5,5]-bicyclic lactam-bromolactones with several aryl Grignard reagents, under palladium catalysis, furnishes diarylmethane-tethered lactam-lactones in synthetically attractive yields, stereoinvertive fashion, and with a tolerance for many functional groups.
View Article and Find Full Text PDFMerging Carbonyl Addition with Photocatalysis.
Acc Chem Res
April 2022
Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149 Münster, Germany.
The carbonyl group stands as a fundamental scaffold and plays a ubiquitous role in synthetically important chemical reactions in both academic and industrial contexts. Venerable transformations, including the aldol reaction, Grignard reaction, Wittig reaction, and Nozaki-Hiyama-Kishi reaction, constitute a vast and empowering synthetic arsenal. Notwithstanding, two-electron mechanisms inherently confine the breadth of accessible reactivity and topological patterns.
View Article and Find Full Text PDFLight Directs Monomer Coordination in Catalyst-Free Grignard Photopolymerization.
J Am Chem Soc
November 2021
Department of Chemistry, Northwestern University, 2145 Sheridan Rd, Evanston, Illinois 60208, United States.
π-Conjugated polymers can serve as active layers in flexible and lightweight electronics and are conventionally synthesized by transition-metal-mediated polycondensation at elevated temperatures. We recently reported a photopolymerization of electron-deficient heteroaryl Grignard monomers that enables the catalyst-free synthesis of n-type π-conjugated polymers. Herein, we describe an experimental and computational investigation into the mechanism of this photopolymerization.
View Article and Find Full Text PDFThiophene-fused boracycles as photoactive analogues of diboraanthracenes.
Chem Commun (Camb)
October 2021
School of Chemical Sciences, National Institute of Science Education and Research (NISER), HBNI, Bhubaneswar-752050, Odisha, India.
The construction of thiophene-fused analogues of diboraanthracenes with different aryl substituents through boron-mercury exchange followed by the nucleophilic replacement of the chlorines of dichlorodiboradithiophene 2 with Grignard reagents is reported. These diboradithiophenes exhibited unusual photophysical and electrochemical properties. They all undergo photoisomerisation, which can be traced using photophysical and H NMR spectroscopy studies.
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