135529-38-3Relevant academic research and scientific papers
Two-dimensional bricklayer arrangements of tolans using halogen bonding interactions
Frausto, Fanny,Smith, Zachary C.,Haas, Terry E.,Thomas, Samuel W.
, p. 8825 - 8828 (2015)
Diphenylacetylene (tolan) derivatives with self-complementary aryl halides and halogen bond-accepting nitriles form 2D bricklayer packing motifs when halogen bonding occurs. When halogen bonding is absent, as occurred with fluorinated aryl bromides, the molecules adopt other packing motifs. These results suggest halogen bonding is potentially useful for producing rarely observed 2D bricklayer motifs in organic semiconductors.
Direct preparation of arylethynylzinc bromides and their application to cross-coupling reactions
Joo, Seong-Ryu,Kim, Jong-Sung,Kim, Seung-Hoi
, p. 3267 - 3270 (2017/07/27)
A novel synthetic protocol for the preparation of arylethynylzinc bromides has been developed. Thus-obtained organozinc reagents were successfully employed in the subsequent cross-coupling reactions with a broad range of aryl halides providing the corresponding alkynylated compounds in good to excellent yields.
Palladium-Catalyzed Desulfitative Cross-Coupling of Arylsulfonyl Hydrazides with Terminal Alkynes: A General Approach toward Functionalized Internal Alkynes
Qian, Liang-Wei,Sun, Mengli,Dong, Jianyu,Xu, Qing,Zhou, Yongbo,Yin, Shuang-Feng
supporting information, p. 6764 - 6769 (2017/07/15)
A palladium-catalyzed Sonogashira-type coupling between arylsulfonyl hydrazides and terminal alkynes via Ar(C)-S bond cleavage is disclosed, which enables the general synthesis of functionalized internal alkynes, especially the Br-substituted ones, in good to excellent yields under acid- and base-free conditions.
Dual gold/photoredox-catalyzed C(sp)-H arylation of terminal alkynes with diazonium salts
Tlahuext-Aca, Adrian,Hopkinson, Matthew N.,Sahoo, Basudev,Glorius, Frank
, p. 89 - 93 (2015/12/30)
The arylation of alkyl and aromatic terminal alkynes by a dual gold/photoredox catalytic system is described. Using aryldiazonium salts as readily available aryl sources, a range of diversely-functionalized arylalkynes could be synthesized under mild, base-free reaction conditions using visible light from simple household sources or even sunlight. This process, which exhibits a broad scope and functional group tolerance, expands the range of transformations amenable to dual gold/photoredox catalysis to those involving C-H bond functionalization and demonstrates the potential of this concept to access AuI/AuIII redox chemistry under mild, redox-neutral conditions.
Synthesis of molecular chains: Application of cross-coupling and bromo by iodo exchange reactions
Fernández-Hernández, Jesús M.,Cámara, Verónica,Vicente, José
, p. 5506 - 5512 (2015/08/03)
The synthesis of a series of molecular chains by use of C-S, C-N and C-Alkyne cross coupling, as well as bromo by iodo exchange reactions, has been reported. Two different types of chains R-C6H4-S-C6H4-CC-C6H4-NH-C6H4-Br, and R-C6H4-S-C6H4-NH-C6H4-CC-C6H4-Br (R=MeO, CN, NO2) could be obtained starting from the same thioether but applying different reaction sequences. Compounds R-C6H4-CC-C6H4-S-C6H4-NH-C6H4-Br were prepared from diaryl acetylenes after two bromo by iodo replacements alternated with a C-S and a C-N cross coupling.
Melamine-based microporous network polymer supported palladium nanoparticles: A stable and efficient catalyst for the sonogashira coupling reaction in water
Shunmughanathan, Murugesan,Puthiaraj, Pillaiyar,Pitchumani, Kasi
, p. 666 - 673 (2015/03/05)
A template consisting of a melamine-based microporous polymer network was synthesized and utilized as a solid support to stabilize palladium nanoparticles; the resulting Pd/SNW1 material showed good catalytic activity in copper-free Sonogashira coupling in water. Various aryl iodides were efficiently coupled with arylacetylenes under very low catalyst loadings in an environmentally benign medium. Hot filtration tests confirmed the heterogeneity of the catalyst, which was reused under the optimized conditions without any significant change in its activity. This simple preparation of the catalyst, the stability of the catalyst, product selectivity, and easy recovery and regeneration indicate the possible utilization of this catalytic system in a multitude of catalyzed reactions and industrial processes. Networking possibilities: A template consisting of melamine-based microporous polymer network is synthesized and utilized as a solid support to stabilize palladium nanoparticles; the resulting Pd/SNW1 material shows good catalytic activity in copper-free Sonogashira coupling in water. Various aryl iodides are efficiently coupled with arylacetylenes under very low catalyst loadings in an environmentally benign medium.
Synthesis and spectroscopic study of phenylenee (poly) ethynylenes substituted by amino or amino/cyano groups at terminal(s):Electronic effect of cyano group on charge-transfer excitation of acetylenic φ-systems
Fang, Jing-Kun,An, De-Lie,Wakamatsu, Kan,Ishikawa, Takeharu,Iwanaga, Tetsuo,Toyota, Shinji,Akita, Shin-Ichi,Matsuo, Daisuke,Orita, Akihiro,Otera, Junzo
supporting information; experimental part, p. 5479 - 5485 (2010/08/19)
To gain insight into substituent electronic effect on charge-transfer excitation of acetylenic p-systems, phenylenee(poly)ethynylenes substituted by Ph2N or Ph2N/cyano groups were synthesized by combination of Sonogashira coupling and double elimination protocol of b-substituted sulfones.These substituted phenyleneethynylenes showed large molar absorption coefficients 3, and emitted strong fluorescence upon UV light irradiation.Phenylenee(poly)ethynylenes, which involve butadiyne or hexatriyne motifs, emitted fluorescence in remarkably lower fluorescence quantum yields FF as their polyethynylene motifs e(C^C)ne expanded.The drastic decrease of fluorescence quantum yields FF were explained in terms of increasing nonradiative reaction rate constants knr, which had been determined by the corresponding fluorescence quantum yields F F and lifetime values s.The emission underwent a large bathochromic shift in polar solvents because the charge-separated excited state is more stabilized than the ground state.Comparison of slope values r in Lippert/Mataga plot for the Ph2N and Ph2N/cyano-substituted phenylenee(poly)ethynylenes revealed that the latter underwent large change of dipole moments upon photo-excitation although highly expanded acetylenic p-systems with cyano group did little.
Efficient synthesis of thioamide terminated molecular wires
Dixon, Sally,Whitby, Richard J.
, p. 8147 - 8150 (2007/10/03)
Bis-thioamide terminated 'molecular wires' are formed in a high yield under mild conditions from readily synthesised bis-nitrile terminated molecules and aqueous ammonium sulfide in DMF.
Synthesis and non-linear properties of disubstituted diphenylacetylene and related compounds
Kondo, Koichi,Fujitani, Takumi,Ohnishi, Noriaki
, p. 429 - 433 (2007/10/03)
A variety of disubstituted diphenylacetylenes and related compounds have been synthesized by a modified Horner-Emmons reaction, and their second harmonic generation (SHG) has been evaluated by the Kurtz powder method. The diphenylacetylenes with weak electron-donating and -withdrawing groups are found to be efficient for SHG, as well as having the lowest cut-off wavelength.
