147492-76-0

Upstream product

• 134856-58-9 1-iodo-4-(trimethylsilylethynyl)benzene 
• 536-74-3 phenylacetylene 
• 17938-13-5 1,4-Bis(trimethylsilylethynyl)benzene 
• 603-36-1 triphenylantimony 
• 16116-78-2 (4-bromophenyl)(trimethylsilyl)acetylene 
• 589-87-7 1,4-bromoiodobenzene 
• 1066-54-2 trimethylsilylacetylene 
• 13667-12-4 1-bromo-4-phenylethynylbenzene 
• 591-50-4 iodobenzene 
• 66228-76-0 4-(trimethylsilylethynyl)phenylacetylene 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 
• 106-40-1 4-bromo-aniline 
• 624-38-4 para-diiodobenzene 
• 886989-34-0 4-[(trimethylsilyl)ethynyl]-1-(3-hydroxyl-3-methylbutynyl)benzene 

Downstream Products

• 92866-00-7 4-ethynyltolane 
• 356590-07-3 1-[(4-(acetylthio)phenyl)ethynyl]-4-[(phenyl)ethynyl]benzene 
• 518342-78-4 trimethyl[4-(4-(phenylethynyl)phenylethynyl)-3-trifluoromethylphenyl-ethynyl]silane 
• 518342-79-5 [3-ethyl-4-(4-phenylethynylphenylethynyl)phenylethynyl]trimethylsilane 
• 518342-77-3 2-(4-(phenylethynyl)phenylethynyl)-5-trimethylsilanylethynylbenzonitrile 
• 518342-76-2 [3-fluoro-4-(4-(phenylethynyl)phenylethynyl)phenylethynyl]trimethylsilane 
• 518342-75-1 trimethyl[4-(4-(phenylethynyl)phenylethynyl)phenylethynyl]silane 
• 106785-01-7 4,4'-bis(phenylethynyl)diphenylethyne 
• 484067-45-0 trimethyl-{4-[4-(4-phenylethynyl-phenylethynyl)-phenylethynyl]-phenylethynyl}-silane 
• 97765-42-9 1,4-bis(4-(phenylethynyl)phenylethynyl)benzene 

Relevant academic research and scientific papers

Zinc-Catalysed Hydroboration of Terminal and Internal Alkynes

A regioselective hydroboration of alkynes has been developed by using commercially available zinc triflate as a catalyst, in the presence of catalytic amount of NaBHEt3. The reaction tolerates a wide range of terminal alkynes having several synthetically useful functional groups and proceeds regioselectively to furnish hydroborated products in moderate to excellent yields. This system shows moderate chemoselectivity towards terminal C≡C bond over terminal and internal C=C bond and internal C≡C bond.

Nickel-Catalyzed Highly Regioselective Hydrocyanation of Terminal Alkynes with Zn(CN)2 Using Water as the Hydrogen Source

The first efficient and general nickel-catalyzed hydrocyanation of terminal alkynes with Zn(CN)2 in the presence of water has been developed. The reaction provides a regioselective protocol for the synthesis of functionalized vinyl nitriles with a range of structural diversity under mild reaction conditions while obviating use of the volatile and hazardous reagent of HCN. Deuterium-labeling experiments confirmed the role of water as the hydrogen source in this hydrocyanation reaction.

Molecular daisy chains: Synthesis and aggregation studies of an amphiphilic molecular rod

A water-soluble cyclophane as the loop subunit, monofunctionalized with a molecular rod, has been synthesized to introduce a new binding motif for mechanically interlinked oligomers. It has been demonstrated that this hermaphroditic compound forms [c2]dai

Stille couplings in water at room temperature

A nonionic amphiphile, TPGS-750-M, enables efficient Stille couplings between a wide range of substrates to be conducted in water as the only medium, in most cases at room temperature.

Fluoro-substituted phenyleneethynylenes: Acetylenic n-type organic semiconductors

Fluoro-substituted phenyleneethynylenes are synthesized by Sonogashira coupling and acetylide-nucleophilic substitution of fluorobenzenes. Fluoro-substitution of benzenes enables deep LUMO potential, and CF 3-substitution provides high electron

Systematic studies on photoluminescence of oligo(arylene-ethynylene)s: Tunability of excited states and derivatization as luminescent labeling probes for proteins

Functionalized oligo(phenylene-ethynylene)s (OPEs) with different conjugation lengths, p-X(C6H4C≡C) nSiMe3 (n = 1-4; X = NH2, NMe2, H) were synthesized by Sonogashira coupling of (phenylene-ethynylene)s and 1-iodo-4-(trimethylsilylethynyl)benzene, followed by desilylation of the p-substituted (trimethylsilylethynyl)benzenes with potassium hydroxide. The photoluminescent properties for the OPE series with different chain lengths and their solvatochromic responses were examined. The absorption maxima were red-shifted with increasing numbers of -(C6H4C≡C)- units (n), and a linear plot of the absorption energy maxima vs. 1/n was obtained for each series. The emission spectra in dichloromethane showed a broad and structureless band, the energies of which (in wavenumbers) also fit linearly with 1/n. Both the absorption and emission wavelength maxima of the NH2- and NMe2-substituted OPEs exhibited significant solvent dependence, whereas the parent OPEs (X = H) showed only minor shifts of the λmax values in different solvents. Substituent effects upon the photoluminescent characteristics of the OPEs and the tunability of the excited states were examined with the p-X(C6H4C≡C) nSiMe3 (n = 2, 3; X = NH2, NMe2, H, SMe, OMe, OH, and F) series. The H- and F-substituted counterparts exhibited high-energy vibronically structured emissions attributed to the 3(ππ*) excited states of the (arylene-ethynylene) backbone. For compounds bearing NH2 and NMe2 groups, a broad red-shifted emission with a remarkable Stokes shift from the respective absorption maximum was observed, which can be assigned to an n → π* transition. The n → π* assignment was supported by MO calculations on the model compounds p-X(C6H4C≡C) 2SiH3 (X = NH2, H). Functionalization of the oligo(arylene-ethynylene)s with the N-hydroxysuccinimidyl (NHS) moiety enabled covalent attachment of the fluorophore to HSA protein molecules. A series of fluorescent labels, namely p-X(C6H4C≡C) n-C6H4NHS, (n = 1, X = NH2, NMe 2, SMe, OMe, OH, F; n = 2, X = NH2, NMe2) and p-Me2NC6H4C≡C(C4H 2S)-C≡CC6H4NHS were synthesized, and their conjugates with HSA (human serum albumin) were characterized by MALDI-TOF mass spectrometry, UV/Vis absorption spectroscopy, and gel electrophoresis. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

New fluorophores with rod-shaped polycyano π-conjugated structures: Synthesis and photophysical properties

Novel rod-shaped polycyano-oligo(phenyleneethynylene)s were synthesized by Pd cross-coupling reaction. Polycyano groups were found to greatly improve the emission efficiency (Φf) of OPEs. By the end donor modification, we achieved the creation of very intense blue light-emitting fluorophore with the SMe group (Φf) = 0.972, log ε 4.89, λ em 455 nm) and very intense yellow light-emitting fluorophore with the NMe2 group (Φf = 0.999, log ε 4.75, λem 555 nm). Contrasting Φf solvent dependency of 6 and 7 and a linear relationship between Φf and σp-X over the whole region of σp-X were also found.

Light-emitting efficiency tuning of rod-shaped π conjugated systems by donor and acceptor groups

In view of the increasing importance of highly efficient light-emitting materials in chemistry, biological science, and materials science, we investigated the light-emitting efficiency tuning of rod-shaped oligo(p-phenylene ethynylene)s (OPEs, trimeric to pentameric systems) by donor and acceptor groups, so that they emit the very intense fluorescence (Φf ≈ 1.0, log ε ≈ 5) at 460 nm as the desired wavelength region. This goal was achieved by side modification by MeO (donor) groups and end modification by a CN-substituted benzene ring or CF3-substituted pyridine ring (acceptor) of tetrameric p-phenylene ethynylene rod-shaped molecules (Φf = 0.96, λem = 458 nm, log ε = 4.96 for the former and Φf = 0.99, λem = 459 nm, log ε = 4.92 for the latter). The high Φf values for 11 and 12 are interpreted in terms of kr (radiative rate constant) and kd (radiationless rate constant). The linear relationship with a positive slope between Φf and the Hammett σ constant was found for the first time. It is found that kd rather than kr varies with σp-X. The photophysical properties (Φf, λem, λabs, log ε) were not so altered with the solvent polarity, which could be explained by the dipole moments in the excited and ground states. The results would be valuable for the molecular design of highly efficient light-emitting materials. Copyright

A simple "palladium-free" synthesis of phenyleneethynylene-based molecular materials revisited

Nucleophilic attack of acetylide anions at the two carbonyl moieties of para-quinones readily affords the corresponding diols. Subsequent reduction with stannous chloride affords a number of useful compounds, including 1,4-bis[(trimethylsilyl)ethynyl]benzene, 1,4-bis[(trimethylsilyl)ethynyl] naphthalene and 9,10-bis[(trimethylsilyl)ethynyl]anthracene. Sequential attack by different acetylide anions followed by reduction provides a useful route to differentially substituted compounds including 1-[(4-nonyloxyphenyl)ethynyl]-4- (phenylethynyl)benzene, a new luminescent liquid-crystalline material. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2005.

Aqueous ammonia as a new activator for Sonogashira coupling

Sonogashira coupling, which is a coupling reaction of terminal alkynes with organic halides, takes place with dilute aqueous ammonia as an activator. The reaction of several terminal alkynes and aryl iodides in the presence of small excess of aqueous ammonia at room temperature furnishes the cross-coupling product in good-to-excellent yields. A water-soluble amine with a high boiling point is alternatively employed for reactions at higher temperatures. A related coupling reaction in the presence of carbon monoxide also proceeded at room temperature and under ambient pressure to afford α,β-alkynyl ketones efficiently.