32870-98-7

Usage

Uses

Used in Chemical Research and Synthesis:
9-Ethynylphenanthrene is utilized as a reactive intermediate in chemical research and synthesis for its unique structure and reactivity. It serves as a building block in the creation of more complex organic molecules and materials, contributing to the advancement of organic chemistry and materials science.
Used in Environmental Analysis:
In environmental analysis, 9-ethynylphenanthrene is identified as a pollutant and a potential carcinogen. It is used in studies aimed at understanding its presence in the environment, its sources, and its effects on ecosystems and human health, thereby informing strategies for pollution control and prevention.
Used in Organic Synthesis:
9-Ethynylphenanthrene is employed as a key component in organic synthesis for the development of new compounds with specific properties. Its ethynyl group and aromatic structure make it a versatile reactant in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Materials Science:
In the field of materials science, 9-ethynylphenanthrene is explored for its potential applications in the creation of new materials with unique electronic, optical, or mechanical properties. Its incorporation into polymers or other materials could lead to advancements in areas such as sensors, electronic devices, or advanced composites.

InChI:InChI=1/C16H10/c1-2-12-11-13-7-3-4-9-15(13)16-10-6-5-8-14(12)16/h1,3-11H

Upstream product

• 2039-77-2 9-acetylphenanthrene 
• 90965-06-3 dimethyl 1-(1-diazo-2-oxopropyl)phosphonate 
• 4707-71-5 Phenanthrene-9-carboxaldehyde 
• 573-17-1 9-bromophenanthrene 
• 75-20-7 calcium carbide 
• 583-55-1 1-Bromo-2-iodobenzene 
• 18442-29-0 2,2′-bis(ethynyl)-1,1′-biphenyl 
• 18238-34-1 2,2′-bis[(trimethylsilyl)ethynyl]biphenyl 
• 38274-16-7 2-bromo-1-(trimethylsilylethynyl)benzene 
• 16331-54-7 phenanthrene-9-carbonyl chloride 
• 191996-61-9 trimethyl(phenanthren-9-ylethynyl)silane 

Downstream Products

• 855749-04-1 4-methyl-N-(2-phenanthren-9-ylethynyl-phenyl)-benzenesulfonamide 
• 1257399-30-6 C₂₇H₂₂Si 
• 1311312-27-2 1-(2-(phenanthren-9-ylethynyl)phenyl)-1H-pyrrole 
• 1384115-67-6 [4-(phenanthren-9-yl)-7,7-diphenyl-7λ5-phosphinino[2,3-b]-furan-6-yl](phenyl)methanone 
• 1421275-98-0 1-(biphenyl-4-yl)-4-(phenanthren-9-yl)-1H-1,2,3-triazole 
• 1448326-00-8 methyl 4-(4-methoxyphenyl)-7,7-diphenyl-7λ⁵-phosphinino[2,3-b]thiophene-6-carboxylate 
• 1448326-02-0 (2-methoxy-5-phenanthren-9-ylfuran-3-yl)(diphenyl)thiophen-2-ylphosphonium tetrafluoroborate 
• 1448326-09-7 methyl 4-(4-methoxyphenyl)-7,7-diphenyl-7λ⁵-phosphinino[2,3-b]furan-6-carboxylate 
• 1448326-11-1 furan-2-yl(2-methoxy-5-phenanthren-9-ylfuran-3-yl)diphenylphosphonium tetrafluoroborate 
• 1448325-88-9 (2-methoxy-5-phenanthren-9-ylfuran-3-yl)(triphenyl)phosphonium tetrafluoroborate 
• 1448325-89-0 methyl 4-(phenanthren-9-yl)-1,1-diphenyl-1λ⁵-phosphinoline-2-carboxylate 
• 2039-77-2 9-acetylphenanthrene 
• 1593267-96-9 1-(2-(hexyloxy)phenyl)-3-(phenanthren-9-yl)prop-2-yn-1-one 

Relevant academic research and scientific papers

Solvent-Dependent Cyclization of 2-Alkynylanilines and ClCF2COONa for the Divergent Assembly of N-(Quinolin-2-yl)amides and Quinolin-2(1 H)-ones

Herein, we present an expedient Cu-catalyzed [5 + 1] cyclization of 2-alkynylanilines and ClCF2COONa to divergent construction of N-(quinolin-2-yl)amides and quinolin-2(1H)-ones by regulating the reaction solvents. Notably, nitrile acts as a solvent and performs the Ritter reactions. ClCF2COONa is used as a C1 synthon in this transformation, which also represents the first example for utilization of ClCF2COONa as an efficient desiliconization reagent. The current protocol involves in situ generation of isocyanide, copper-activated alkyne, Ritter reaction and protonation.

Polycyclic aromatic hydrocarbon-substituted push-pull chromophores: An investigation of optoelectronic and nonlinear optical properties using experimental and theoretical approaches

A series of new push-pull chromophores were synthesized in moderate to very high yields (65%-97%) by treating TCNE and TCNQ with alkynes substituted by electron-rich diethylaniline and polycyclic aromatic hydrocarbons. Some of the chromophores exhibit strong intramolecular charge-transfer bands in the near-IR region with λmax values between 695 and 749 nm. With the help of experimental and theoretical analysis, it is concluded that the trend in λmax values is affected by PAH substituents sterically, not electronically. Steric constraints led to the increased dihedral angles, reducing conjugation efficiencies. The absorption properties of push-pull compounds have been investigated in solvents possessing different polarities. All chromophores exhibited positive solvatochromism. As an additional proof of efficient charge-transfer in push-pull chromophores, quinoid character (dr) values were predicted using calculated bond lengths. Remarkably, substantial dr values (0.045-0.049) were predicted for donor diethylaniline rings in all compounds. The effects of various polycyclic aromatic hydrocarbons on optical and nonlinear optical properties were also studied by computational methods. Several parameters, such as band gaps, Mulliken electronegativity, chemical hardness and softness, dipole moments, average polarizability, first hyperpolarizability, were predicted for chromophores at the B3LYP/6-31++G(d,p) level of theory. The predicted first hyperpolarizability β(tot) values vary between 198 to 538 × 10-30 esu for the reported push-pull chromophores in this study. The highest predicted β(tot) value in this study is 537.842 × 10-30 esu, 8150 times larger than the predicted β(tot) value of benchmark NLO material urea, suggests possible utilization of these chromophores in NLO devices. The charge-transfer character of the synthesized structures was further confirmed by HOMO-LUMO depictions and electrostatic potential maps.

Direct Exploitation of the Ethynyl Moiety in Calcium Carbide Through Sealed Ball Milling

Ball milling of calcium carbide (CaC2) enables the reaction of its ethynyl moiety with organic electrophiles. This was realized simply by co-milling CaC2 with organic substrates in a sealed jar without the need for an additive or a catalyst. Various ketones including those bearing α-hydrogens were ethynylated in good yields at short reaction times. Aryl halides are also amenable substrates for this protocol as they furnish aryl ethynes through a benzyne intermediate. This method offers a practical and cheap alternative to the established procedures for introducing ethynyl functionalities.

Efficient Microwave-Assisted Synthesis of Sonogashira-Coupled Perylene Monoimide Derivatives: Impact of Electron-Donating Groups on Optoelectronic Properties

An efficient microwave-assisted Sonogashira-coupling protocol for the synthesis of peri-functionalized perylene monoimide dye derivatives was developed. This method was found to be significantly faster than the conventional coupling method and provided pr

Ruthenium-Catalyzed Cycloisomerization of 2,2′-Diethynyl- biphenyls Involving Cleavage of a Carbon-Carbon Triple Bond

A ruthenium complex catalyzes a new cycloisomerization reaction of 2,2′-diethynylbiphenyls to form 9-ethynylphenanthrenes, thereby cleaving the carbon-carbon triple bond of the original ethynyl group. A metal-vinylidene complex is generated from one of th

Aerobic oxynitration of alkynes with tBuONO and TEMPO

An efficient method for stereoselective nitroaminoxylation of alkyne has been reported. The reaction enjoys a broad substrate scope, good functional group tolerance, and high yields. Synthetically useful α-nitroketones can be accessed through these products in a single step.

Regio- and stereoselective dimerization of arylacetylenes and optical and electrochemical studies of (E)-1,3-enynes

The N-heterocyclic carbene palladium complex (SIPr)Pd(cinnamyl)Cl [SIPr=N,N'-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene) promotes regio- and stereospecific dimerization of a variety of arylalkynes to give (E)-1,3-enynes in good to excellent yields. An efficient and practical procedure for their synthesis was developed using a biphasic aqueous alkali/heptane system. Optical and electronic properties of (E)-1,3-enynes are highly tunable. Depending on the nature of the substituents, HOMO energies vary in the range 5.3-6.0eV. (E)-1,3-Enynes can exhibit intense photoluminescence in the spectral region 350-500nm.

Synthesis and optical properties of molecular rods comprising a central core-substituted naphthalenediimide chromophore for carbon nanotube junctions

The synthesis of a series of molecular rods 1-5, designed to bridge the gap of a carbon nanotube junction in order to emit light as a characteristic signal of integrated molecules, is reported. The molecular rods consist of a central naphthalenediimide (NDI) core, which itself is substituted with benzylamino and benzylsulfanyl groups, providing distinct absorption and emission properties. The NDI core is embedded in an oligo(phenylene ethynylene) (OPE) system providing the rod-like structure required to bridge gaps between nanoelectrodes. The number of repeating units of the OPE is varied to adjust the length of the target compounds between 2.3 and 6.6 nm. The OPE parts are terminally functionalized with polyaromatic hydrocarbon groups (naphthalene, phenanthrene, anthracene or pyrene), which possess affinity with the surface of the carbon nanotubes due to van der Waals interactions. Synthetic protocols based on Sonogashira-Hagihara couplings were developed to build up the OPE backbone. Bifunctional iodophenyl acetylene derivative 33 served as a key building block in a coupling-deprotecting-coupling sequence. The NDI building block was synthesized by an aromatic nucleophilic substitution reaction of 2,6-dichloro-1,4,5,8-tetracarboxylic acid naphthalenediimide derivative 9 and the corresponding amine and sulfide (i.e., 11, 12), respectively. The convergent synthesis allows modular assembly of the NDI and OPE parts in a final Sonogashira-Hagihara coupling reaction. The target structures were fully characterized by NMR spectroscopy and mass spectrometry. Further, the optical properties of compounds 3-5 in solution, and on a graphene surface were qualitatively investigated. A Dexter-type energy transfer from the OPE unit to the NDI unit was observed. The studies of target structures 3-5 revealed that diamino-functionalized compound 3 is ideally suited for the envisaged single molecule electroluminescence experiments. The synthesis of a series of over 6-nm long modular rods with a central decoupled naphthalenediimide (NDI) chromophore isreported. Their spectroscopic properties are adjusted by varying the substituents of the NDI core

Pentacene-based polycyclic aromatic hydrocarbon dyads with cofacial solid-state π-stacking

An efficient, stepwise route to unsymmetrically 6, 13-disubstituted pentacenes for the formation of pentacene-based polycyclic aromatic hydrocarbons (PAH) dyads has been reported. PAH are a class of compounds that has received attention from the fields of organic chemistry, materials chemistry, theoretical chemistry, cancer research, environmental science, and astronomy. The stability of PAH materials was assessed by thermal gravimetric analysis (TGA) and differential scanning calorimetry. UV/Vis spectroscopy (CH2CL 2) was used to explore the electronic outcome of varying the PAH partner connected to the pentacene moiety. X-ray crystallography reveals that with increasing size of the pendent PAH group, cofacial packing is maximized between nearest neighbors. This fact should provide for a larger transfer integral, and, thus, enhanced conduction and improved charge-carrier mobility.

Sequential Seyferth-Gilbert/CuAAC reactions: Application to the one-pot synthesis of triazoles from aldehydes

A reliable and operationally simple one-pot reaction for a one-carbon homologation of various aldehydes followed by a Cu-catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuAAC) is reported. 1,4-Disubstituted 1,2,3-triazoles are obtained in good to excellent yields from a variety of readily available aldehydes without the need for isolation of the alkyne intermediates. The reaction has a broad scope, allows the formation of new bioconjugates and is applied for the synthesis of new boronic acid based fluorescent sensors. Georg Thieme Verlag Stuttgart.