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.
A CONVENIENT MASKING GROUP FOR ARYL IODIDES
Moore, Jeffrey S.,Weinstein, Edward J.,Wu, Ziyan
, p. 2465 - 2466 (1991)
1-Aryl-3,3-dialkyltriazenes give excellent yields of easily isolated aryl iodides upon treatment with methyl iodide.
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
Sequential catalytic synthesis of rod-like conjugated poly-ynes
Lavastre, Olivier,Ollivier, Laurence,Dixneuf, Pierre H.,Sibandhit, Sourisak
, p. 5495 - 5504 (1996)
Several poly-ynes X-[C ≡ C-C6H4-](n)C ≡ C-Si(i)Pr3 (X = H, SiMe3) with controlled length (n = 1, 2, 3, 4) have been prepared from the easily accessible 4-trimethylsilylethynyl iodobenzene by using iterative and convergent methods based on both Pd/Cu catalysed C-C cross-coupling and selective desilylation reactions.
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.
Synthesis and Solution Aggregation of Polystyrene-Oligo(p-phenyleneethynylene)-Polystyrene Triblock Copolymer
Li, Kun,Wang, Qing
, p. 1172 - 1174 (2004)
The solution aggregation and synthesis of polystyrene-oligo(p-phenyleneethynylene) (OPE)-polystyrene triblock copolymer are studied. Variation of physicochemical interactions between the relative lengths of the blocks and the constituent blocks allow a tailoring of morphologies. The use of the solvent composition to influence chain conformations is also demonstrated. It is found that the triblock copolymer exhibits unique solvatochromatic behaviors through planarization of the conjugated backbone and aggregation-induced π-π stacking.
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.
Regio- and stereoselective synthesis of bromoalkenes by homolytic hydrobromination of alkynes with hydrogen bromide
Kumaki, Wataru,Kinoshita, Hidenori,Miura, Katsukiyo
supporting information, (2022/03/07)
Homolytic hydrobromination of terminal and internal alkynes with a commercially available solution of hydrogen bromide in acetic acid has been investigated for regio- and stereoselective synthesis of bromoalkenes. Under an aerobic atmosphere at room temperature, the reaction of ethynylarenes with a small excess of HBr efficiently gave (2-bromoethenyl)arenes with good to high E-selectivity. (Alk-1-ynyl)arenes, or internal alkynes bearing both phenyl and alkyl groups at the sp-carbons also underwent the air-initiated hydrobromination to exhibit high Z-selectivity under kinetic conditions using a half equivalent of HBr.
Dendritic polyphenylene framework as a light-harvesting shell for highly emissive [2.2]Paracyclophane core
Antonov, Dmitrii Yu.,Krasnova, Irina Yu.,Shapovalov, Alexey V.,Shifrina, Zinaida B.
, (2021/10/07)
New polyphenylene type dendrimers of two generations were developed through attaching the aromatic dendron units to the highly emissive conjugated 4,7,12,15-tetra(phenylethynyl)[2.2]paracyclophane core via the Diels-Alder reaction. The polyphenylene moieties in dendrimers efficiently absorbed the UV light, followed by the energy transfer to the [2.2]paracyclophane core, resulting in photoluminescence with high quantum yields from the core unit and demonstrating efficient intramolecular energy transfer. The detailed analysis of optical properties of polyphenylene dendrimers with the [2.2]paracyclophane core was carried out using parent model compounds that resemble the constituents of respective dendrimers. The success of this study became possible to a certain extent due to an improvement of the synthetic procedure for 4,7,12,15-tetraethynyl substituted [2.2]paracyclophane derivatives allowing for high yields of target products.
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.
