17573-94-3

Usage

Uses

Used in Chemical Synthesis:
4'-DIMETHYLAMINOPHENYL ACETYLENE is used as a synthetic intermediate for the creation of various complex organic molecules and materials. Its unique structure allows for further functionalization and incorporation into a wide range of applications.
Used in Copper(I) Arylacetylide Synthesis:
4'-DIMETHYLAMINOPHENYL ACETYLENE is used as a starting material for the synthesis of copper(I) arylacetylide via a reaction with copper(II) acetate. This application is significant in the development of new copper-based compounds with potential applications in various fields, such as catalysis and materials science.
Used in Sonogashira–Hagihara Coupling:
In the field of organic chemistry, 4'-DIMETHYLAMINOPHENYL ACETYLENE is used as a reactant in the Sonogashira–Hagihara coupling with 3-iodopyridine. This coupling reaction is a powerful method for the formation of carbon-carbon bonds, leading to the synthesis of N,N-dimethyl-4-(3-pyridinylethynyl)aniline, which can be further utilized in the development of novel organic compounds and materials.
Used in Porphyrin Chemistry:
4'-DIMETHYLAMINOPHENYL ACETYLENE is used as a key component in the synthesis of complex porphyrin derivatives, such as [5,15-bis[(40-dimethylamino)phenyl]ethynyl]-10,20-bis[(triisopropylsilyl)ethynyl]porphyrinato]magnesium(II), through a reaction with dibromo magnesium porphyrin. Porphyrin-based compounds have a wide range of applications, including in the fields of photovoltaics, catalysis, and biomedicine.

Upstream product

• 519-73-3 triphenylmethane 
• 136482-75-2 C₁₀H₁₀KN 
• 56512-48-2 4-(3-methyl-3-hydroxy-1-butynyl)-N,N-dimethylaniline 
• 156780-40-4 (Z)-β-bromo-4-(N,N-dimethylamino)styrene 
• 55894-19-4 p-dimethylamino-α-bromostyrene 
• 586-77-6 4-bromo-N,N-dimethylaniline 
• 1066-54-2 trimethylsilylacetylene 
• 2124-31-4 4'-dimethylaminoacetophenone 
• 56506-90-2 (dibromomethyl)(triphenyl)phosphonium bromide 
• 100-10-7 4-dimethylamino-benzaldehyde 
• 121-69-7 N,N-dimethyl-aniline 
• 698-70-4 4-Iodo-N,N-dimethylaniline 
• 193957-50-5 3-(4-(N,N-dimethylamino)phenyl)prop-2-yn-1-ol 
• 124-38-9 carbon dioxide 

Downstream Products

• 42289-93-0 [4-(4-Chloro-3,3,4-trifluoro-cyclobut-1-enyl)-phenyl]-dimethyl-amine 
• 40470-56-2 (E)-4,4'-(but-1-en-3-yne-1,4-diyl)bis(N,N-dimethylbenzenamine) 
• 58300-70-2 bis(p-dimethylaminophenyl)butadiyne 
• 59675-58-0 4-dimethylamino-ω-diphenylphosphinyl-trans-styrene 
• 242487-89-4 1-phenyl-5-(4-N,N-dimethylaminophenyl)-1,4-pentadiyn-3-ol 
• 242487-86-1 1,5-bis(4-N,N-dimethylaminophenyl)-1,4-pentadiyn-3-ol 
• 289481-37-4 5',3'-bis-O-tert-butyldimethylsilyl-5-[2-(4-N,N-dimethylaminophenyl)ethynyl]-2'-deoxyuridine 
• 288311-31-9 1-[4-(dimethylamino)phenyl]-6-(triisopropylsilyl)-4-[2-(triisopropysilyl)ethynyl]-3-[2-(trimethylsilyl)ethynyl]hex-3-ene-1,5-diyne 
• 480430-25-9 2-cyano-3-{[4-(dimethylamino)phenyl]ethynyl}but-2-ene-dinitrile 
• 885325-36-0 1-[p-(3-hydroxy-3-methyl-1-butynyl)phenyl]-2-(p-N,N-dimethylaminophenyl)ethyne 
• 193957-50-5 3-(4-(N,N-dimethylamino)phenyl)prop-2-yn-1-ol 

Relevant academic research and scientific papers

Benzobisimidazole Cruciform Fluorophores

A series of 11 cross-conjugated cruciform fluorophores based on a benzobisimidazole nucleus has been synthesized and characterized. Like in their previously reported benzobisoxazole counterparts, the HOMOs of these new fluorophores are localized along the vertical bisethynylbenzene axes, while their LUMOs remain relatively delocalized across the molecule, except in cruciforms substituted with electron-withdrawing groups along the vertical axis. Benzobisimidazole cruciforms exhibit a pronounced response to deprotonation in their UV/vis absorption and emission spectra, but their response to protonation is significantly attenuated. (Chemical Equation Presented).

Synthesis and non-linear optical properties of new ionic species: Tolan and diphenylbutadiyne with trimethylammonio and dimethylamino groups

As new ionic organic species for second-order non-linear optical (NLO) materials, 4-{[4-(dimethylamino)phenyl]ethynyl)phenyltrimethylarnmonium iodide (1a), 4-{[4-(dimethylamino)phenyl]butadiynyl}phenyltri-methylammoniura iodide (2a) and their derivatives

A Porous and Solution-Processable Molecular Crystal Stable at 200 °c: The Surprising Donor-Acceptor Impact

We report a curious porous molecular crystal that is devoid of the common traits of related systems. Namely, the molecule does not rely on directional hydrogen bonds to enforce open packing, and it offers neither large concave faces (i.e., high internal f

Synthesis and optical properties of conjugated N,N-dimethyl and thienyl end-capped 2,5-(arylethynyl)thiophene oligomer structures

End-capped (N,N-dimethylaminophenyl) and 2′-thienylethynyl 2,5-thiophene oligomer structures were synthesized by heterocoupling between the terminal acetylenes such as: p-(N,N-dimethylaminophenyl)ethyne (3) [or 1-(p-(N,N-dimethylaminophenyl)-2-p-(ethynylp

Synthesis, Crystal Structures, and Solid-State Polymerization of 8?[4-(Dimethylamino)phenyl]octa-5,7-diynyl Carbamates

Six butadiyne monomers with (dimethylamino)phenyl and N-substituted urethane substituents were synthesized and their crystal structures and solid-state polymerization were investigated. In five of the six monomers, directions of the butadiyne stacking and

A twisted-intramolecular-charge-transfer (TICT) based ratiometric fluorescent thermometer with a mega-Stokes shift and a positive temperature coefficient

The fluorescence intensity of N,N-dimethyl-4-((2-methylquinolin-6-yl)ethynyl)aniline exhibits an unusual intensification with increasing temperature, by activating more vibrational bands and leading to stronger TICT emissions upon heating in dimethyl sulfoxide. Based on the different temperature dependence at various wavelengths, as shown in the TICT fluorescence spectrum, this dye can be employed to ratiometrically detect temperature.

Synthesis and Solid-State Polymerization of 4-(Dimethylamino) phenylbutadiyne Derivatives and Their Charge-Transfer Complexes

(Five urethane derivatives of 8-[4-(dimethylamino)phenyl]octa-5,7-diyn-1-ol were synthesized. They could be polymerized in the solid state to give conjugated backbones although structural regularity seemed to be not so high. Formability of chargetransfer

Are alkynyl spacers in ancillary ligands in heteroleptic bis(diimine)copper(I) dyes beneficial for dye performance in dye-sensitized solar cells?

The syntheses of 4,40-bis(4-dimethylaminophenyl)-6,60-dimethyl-2,20-bipyridine (1), 4,40-bis(4-dimethylaminophenylethynyl)-6,60-dimethyl-2,20-bipyridine (2), 4,40-bis(4-diphenylaminophenyl)-6,60-dimethyl-2,20-bipyridine (3), and 4,40-bis(4-diphenylaminophenylethynyl)-6,60-dimethyl-2,20-bipyridine (4) are reported along with the preparations and characterisations of their homoleptic copper(I) complexes [CuL2][PF6] (L = 1-4). The solution absorption spectra of the complexes exhibit ligand-centred absorptions in addition to absorptions in the visible region assigned to a combination of intra-ligand and metal-to-ligand charge-transfer. Heteroleptic [Cu(5)(Lancillary)]+ dyes in which 5 is the anchoring ligand ((6,60-dimethyl-[2,20-bipyridine]-4,40-diyl)bis(4,1-phenylene))bis(phosphonic acid) and Lancillary = 1-4 have been assembled on fluorine-doped tin oxide (FTO)-TiO2 electrodes in dye-sensitized solar cells (DSCs). Performance parameters and external quantum efficiency (EQE) spectra of the DSCs (four fully-masked cells for each dye) reveal that the best performing dyes are [Cu(5)(1)]+ and [Cu(5)(3)]+. The alkynyl spacers are not beneficial, leading to a decrease in the short-circuit current density (JSC), confirmed by lower values of EQEmax. Addition of a co-absorbent (n-decylphosphonic acid) to [Cu(5)(1)]+ lead to no significant enhancement of performance for DSCs sensitized with [Cu(5)(1)]+. Electrochemical impedance spectroscopy (EIS) has been used to investigate the interfaces in DSCs; the analysis shows that more favourable electron injection into TiO2 is observed for sensitizers without the alkynyl spacer and confirms higher JSC values for [Cu(5)(1)]+,.

Combinatorial synthesis of new fluorescent scaffolds using click chemistry

Azides and acetylenes are bio-orthogonal functional groups that can be readily coupled using copper(I)- or ruthenium(II)- catalyzed 1,3-dipolar cycloaddition reactions. Using non-fluorescent aromatic azides and aromatic acetylenes, covering a range of electron rich and poor building blocks, the Huisgen cycloaddition afford 1,4-disubstituted or 1,5-disubstituted 1,2,3-triazoles. Using a combinatorial approach by running reaction in parallel in polypropylene 96-well plates we discovered several new fluorescent 1,2,3-triazoles scaffolds. These compounds show diverse interactions with biomolecules that could find applications in biology in, for example, fluorescence microscopy or biomolecule quantification.

Cobalt-Catalyzed Hydroalkynylation of Vinylaziridines

Transition metal-catalyzed hydroalkynylation reactions are efficient transformations allowing the straightforward formation of functionalized alkynes. Therein, we disclose the cobalt-catalyzed hydroalkynylation of vinylaziridines giving rise to both linea