134856-58-9Relevant articles and documents
Solvent-free Sonogashira coupling reaction via high speed ball milling
Fulmer, Dennis A.,Shearouse, William C.,Medonza, Shareika T.,MacK, James
, p. 1821 - 1825 (2009)
Herein, we report on the solvent-free Sonogashira reaction utilizing high speed ball milling. Sonogashira coupling of a variety of para substituted aryl halides were performed with trimethylsilylacetylene or phenylacetylene. We observed that iodo and bromo substituted aromatics successfully undergo Sonogashira coupling. However, chloro and fluoro substituted aryl compounds were unreactive. Conducting the coupling reaction in the absence of copper iodide led to low yields. Alternately, if the reaction is conducted with a copper ball in a copper vial in lieu of copper iodide, the coupling product is observed in high yields. This demonstrates the first report on the use of the vial and ball material as a catalyst in a ball milled chemical reaction. The Royal Society of Chemistry 2009.
Supramolecular hierarchy among halogen-bond donors
Aakeroey, Christer B.,Baldrighi, Michele,Desper, John,Metrangolo, Pierangelo,Resnati, Giuseppe
, p. 16240 - 16247 (2013)
Through a combination of structural chemistry, vibrational spectroscopy, and theory, we have systematically examined the relative structure-directing importance of a series of ditopic halogen-bond (XB) donors. The molecular electrostatic potential surfaces of six XB donors were evaluated, which allowed for a charge-based ranking. Each molecule was then co-crystallized with 21 XB acceptors and the results have made it possible to map out the supramolecular landscape describing the competition between I/Br-ethynyl donors, perfluorinated I/Br donors, and I/Br-phenyl based donors. The results offer practical guidelines for synthetic crystal engineering driven by robust and directional halogen bonds. Copyright
Synthesis, photophysical and thin-film self-assembly properties of novel fluorescent molecules with carbon-carbon triple bonds
Niu, Qingfen,Sun, Hongjian,Li, Xiaoyan
, p. 229 - 240 (2014)
Three novel fluorescent molecules with carbon-carbon triple bonds 2TBEA, 2TBDA and TEPEB are successfully designed and synthesized. Their thermal, photophysical, electrochemical, electronic and thin-film self-assembly properties were characterized. Three dyes showed typical photoluminescence (PL) emission behaviors, the PL intensities firstly increased and then decreased with gradually decreasing concentration. The appealing fluorescence properties indicated that three dyes could be used as good fluorescent materials. Additionally, the thin-film self-assembly behaviors of three dyes were also investigated. The microstructures of their optical microscopy (OM) images exhibited high flexibility. Furthermore, SEM and AFM surface morphology of these self-assembly nanostructures revealed that three well-defined long-range order of rod-like and tube-like self-assembly systems exhibited interesting morphology properties. Therefore, three compounds may be of great interest for the development of organic thin-film materials.
Multiple self-assembled nanostructures from an oligo(p-phenyleneethynylene) containing rod-coil-rod triblock copolymer
Li, Kun,Wang, Qing
, p. 4786 - 4788 (2005)
Induced by systematic variation of the initial polymer concentration in toluene, various morphologies of aggregates including vesicles, spheres, onion-like structures, and worm-like fibers from a rod-coil-rod triblock copolymer, oligo(p-phenyleneethynylene)-polystyrene-oligo(p-phenyleneethynylene) , were observed by transmission electron microscopy. The Royal Society of Chemistry 2005.
Palladium-Catalyzed Decarbonylative Iodination of Aryl Carboxylic Acids Enabled by Ligand-Assisted Halide Exchange
Boehm, Philip,Cacherat, Bastien,Lee, Yong Ho,Martini, Tristano,Morandi, Bill
supporting information, p. 17211 - 17217 (2021/07/02)
We report an efficient and broadly applicable palladium-catalyzed iodination of inexpensive and abundant aryl and vinyl carboxylic acids via in situ activation to the acid chloride and formation of a phosphonium salt. The use of 1-iodobutane as iodide source in combination with a base and a deoxychlorinating reagent gives access to a wide range of aryl and vinyl iodides under Pd/Xantphos catalysis, including complex drug-like scaffolds. Stoichiometric experiments and kinetic analysis suggest a unique mechanism involving C?P reductive elimination to form the Xantphos phosphonium chloride, which subsequently initiates an unusual halogen exchange by outer sphere nucleophilic substitution.
Photocatalyzed E→Z Contra-thermodynamic Isomerization of Vinyl Boronates with Binaphthol
Brégent, Thibaud,Bouillon, Jean-Philippe,Poisson, Thomas
supporting information, p. 13966 - 13970 (2021/08/25)
The photocatalytic contra-thermodynamic E→Z isomerization of vinyl boronates by using a binaphthol catalyst is disclosed. The reaction, based on the transient formation of a suitable chromophore with a BINOL derivative as the catalyst, allowed geometrical isomerization in good-to-excellent Z/E ratio and excellent-to-quantitative yields. The mechanism of this E→Z contra-thermodynamic isomerization was studied, and the formation of a transient chromophore species is suggested.
