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A triple bond in chemistry is a chemical bond between two atoms involving six bonding electrons instead of the usual two in a covalent single bond. Triple bonds are stronger than the equivalent single bonds or double bonds, with a bond order of three. The most common triple bond is in a nitrogen N2 molecule; the second most common is that between two carbon atoms, which can be found in alkynes. Other functional groups containing a triple bond are cyanides and isocyanides. Some diatomic molecules, such as dinitrogen and carbon monoxide, are also triple bonded. In skeletal formulae the triple bond is drawn as three parallel lines (≡) between the two connected atoms. Bonding The types of bonding can be explained in terms of orbital hybridization. In the case of acetylene each carbon atom has two sp-orbitals and two p-orbitals. The two sp-orbitals are linear with 180° angles and occupy the x-axis (cartesian coordinate system). The p-orbitals are perpendicular on the y-axis an

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Reto Frei, Durga Prasada Rao Hari, Jérôme Waser, Matthew Wodrich

Among all functional groups, alkynes occupy a privileged position in synthetic and medicinal chemistry, chemical biology, and materials science. Thioalkynes, in particular, are highly useful, as they combine the enhanced reactivity of the triple bond with a sulfur atom frequently encountered in bioactive compounds and materials. Nevertheless, general methods to access these compounds are lacking. In this article, we describe the mechanism and full scope of the alkynylation of thiols using ethynyl benziodoxolone (EBX) hypervalent iodine reagents. Computations led to the discovery of a new, three-atom concerted transition state with a very low energy barrier, which rationalizes the high reaction rate. On the basis of this result, the scope of the reaction was extended to the synthesis of aryl- and alkyl-substituted alkynes containing a broad range of functional groups. New sulfur nucleophiles such as thioglycosides, thioacids, and sodium hydrogen sulfide were also alkynylated successfully to lead to the most general and practical method yet reported for the synthesis of thioalkynes.

2014

Copper-Catalyzed Alkynylation of Hydrazides: An Easy Access to Functionalized Azadipeptides

Julien Aymeric Borrel, Eliott Hugo Joran Le Du, Jérôme Waser

We report a copper-catalyzed alkynylation of azadipeptides using ethynylbenziodoxolone (EBX) reagents. Nonsymmetrical ynehydrazides could be obtained in 25–97% yield using azaglycine derivatives as nucleophiles. The transformation is compatible with most functional groups naturally occurring on amino acid side chains and allows the transfer of silyl-, alkyl-, and aryl-substituted alkynes. The obtained α-alkynyl azaglycine products could be further functionalized by nucleophilic attack or cycloaddition on the triple bond.

2022

Molecular Design of Anthracene-Bridged Metal-Free Organic Dyes for Efficient Dye-Sensitized Solar Cells

Ming Cheng, Ulf Anders Hagfeldt, Chao Yang

Metal-free org. dyes bridged by anthracene-contg. π-conjugations were designed and synthesized as new chromophores for dye-sensitized solar cells (DSSCs). Studies on the relation between the dye structure, photophys. properties, electrochem. properties and performances of the DSSCs are described. With the introduction of the anthracene moiety, together with a triple bond for the fine-tuning of mol. planar configurations and to broaden absorption spectra, the Jsc and Voc of DSSCs improved. The improvement of Jsc is attributed to a broader absorption spectra of the dyes with the anthracene moiety. EIS anal. reveals that the anthracene moiety suppresses charge recombination arising from electrons in TiO2 films with I3- ions in the electrolyte, thus improving Voc. From optimized mol. structures and DSSC test conditions, the dye TC501 shows a prominent solar energy conversion efficiency up to 7.03% (Jsc = 12.96 mA/cm2, VOC = 720 mV, ff = 0.753) under simulated AM 1.5 irradn. (100 mW/cm2).

2010

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Carbon () is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent—its atom making four electrons available to form covalent chemical bonds. It belongs to group 1

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