844-20-2

Usage

Uses

Used in Organic Chemistry:
9-Phenylphenanthrene is used as a building block in organic chemistry for various organic synthesis reactions. Its unique structure allows for the formation of a wide range of functionalized organic compounds, making it a valuable component in the synthesis of complex organic molecules.
Used in Material Science:
In the field of material science, 9-Phenylphenanthrene is used as a starting material for the preparation of other functionalized organic compounds. Its versatile structure enables the development of new materials with improved properties, such as enhanced stability, reactivity, or selectivity.
Used in Organic Semiconductor Materials:
9-Phenylphenanthrene is of interest in the study of organic semiconductor materials due to its potential electronic and optical properties. Its unique molecular structure allows for the development of new semiconductor materials with improved performance, such as higher charge carrier mobility or better light absorption.
Used in Medicinal Chemistry:
9-Phenylphenanthrene has been studied for its potential bioactive properties and is the subject of ongoing research in the field of medicinal chemistry. Its unique structure and potential biological activity make it a promising candidate for the development of new drugs and therapeutic agents.

InChI:InChI=1/C20H14/c1-2-8-15(9-3-1)20-14-16-10-4-5-11-17(16)18-12-6-7-13-19(18)20/h1-14H

Upstream product

• 110-89-4 piperidine 
• 60-29-7 diethyl ether 
• 947-72-8 9-chlorophenanthrene 
• 591-51-5 phenyllithium 
• 501680-77-9 1-biphenyl-2-yl-2-methoxy-ethanone 
• 58-72-0 Triphenylethylene 
• 86569-77-9 9-cyclohex-1-enyl-phenanthrene 
• 444915-08-6 9-phenyl-1,2,3,4,5,6,7,8-octahydrophenanthrene 
• 91083-70-4 9-methoxy-10-phenyl-phenanthrene 
• 855926-80-6 2-biphenyl-2-yl-3-oxo-3-phenyl-propionitrile 
• 412323-50-3 1-biphenyl-2-yl-2-phenoxy-1-phenyl-ethanol 
• 1174-67-0 4-benzyl-2,4-diphenyl-5,6,7,8-tetrahydro-4H-chromene 
• 4707-75-9 (2-(2-bromophenyl)ethene-1,1-diyl)dibenzene 
• 67093-57-6 9-Phenyl-1,2,4a,10a-tetrahydro-phenanthrene 

Downstream Products

• 5235-80-3 9,10-dihydro-9-phenylphenanthrane 
• 6630-85-9 2'-benzoyl[1,1'-biphenyl]-2-carboxylic acid 
• 851901-84-3 9-bromo-10-phenylphenanthrene 

Relevant academic research and scientific papers

Radiative depopulation of the excited intramolecular charge-transfer state of 9-(4-(N,N-dimethylamino)phenyl)phenanthrene

Intramolecular photoinduced electron transfer in 9-(p-N,N-dimethylanilino)phenanthrene (9DPhen) has been studied in solution. The solvent dependence of the fluorescence spectra of 9DPhen indicates that the emission occurs from a highly polar excited state

Rediscovering Bacon's hydrazine/phenylhydrazine mediated cyclization of 2,2′-dicarbonylbi(hetero)aryls: Construction of (5-azo)-/indazolo[2,3-: A] quinolines

Hydrazine/phenylhydrazine-mediated reductive dicarbonyl coupling reactions have been carried out under mild conditions to provide polycyclic aromatic compounds and azo-substituted polyaromatic compounds. This method has a broad substrate scope with good functional group compatibility. This journal is

Compound, electron transport material, organic electroluminescent device and display device

The present application provides a compound of general formula (I), which can be used in electron transport materials. The compound has a mother structure of sym-triphenyl diphenanthrene substituted triazine, has high bond energy between atoms, has good t

Palladium-Catalyzed Sequential Vinyl C–H Activation/Dual Decarboxylation: Regioselective Synthesis of Phenanthrenes and Cyclohepta[1,2,3-de]naphthalenes

The application of a C(vinyl), C(aryl)-palladacycle from vinyl-containing substrates is challenging due to the interference of a reactive double bond in palladium catalysis. This Letter describes a [4 + 2] or [4 + 3] cyclization based on a C(vinyl), C(aryl)-palladacycle by employing α-oxocarboxylic acids as the insertion units under a palladium/air system. The reaction proceeded through the key vinyl C–H activation and dual decarboxylation sequence, forming phenanthrenes and cyclohepta[1,2,3-de]naphthalenes regioselectively in good yields. The synthetic versatility of this protocol is highlighted by the gram-scale synthesis and synthesizing functional material molecule.

Alumina-Mediated π-Activation of Alkynes

The ability to induce powerful atom-economic transformation of alkynes is the key feature of carbophilic π-Lewis acids such as gold- and platinum-based catalysts. The unique catalytic activity of these compounds in electrophilic activations of alkynes is explained through relativistic effects, enabling efficient orbital overlapping with π-systems. For this reason, it is believed that noble metals are indispensable components in the catalysis of such reactions. In this study, we report that thermally activated γ-Al2O3activates enynes, diynes, and arene-ynes in a manner enabling reactions that were typically assigned to the softest π-Lewis acids, while some were known to be triggered exclusively by gold catalysts. We demonstrate the scope of these transformations and suggest a qualitative explanation of this phenomenon based on the Dewar-Chatt-Duncanson model confirmed by density functional theory calculations.

Tris-NHC-propagated self-supported polymer-based Pd catalysts for heterogeneous C-H functionalization

Three-dimensionally propagated imidazolium-containing mesoporous coordination polymer and organic polymer-based platforms were successfully exploited to develop single-site heterogenized Pd-NHC catalysts for oxidative arene/heteroarene C-H functionalization reactions. The catalysts were efficient in directed arene halogenation, and nondirected arene and heteroarene arylation reactions. High catalytic activity, excellent heterogeneity and recyclability were offered by these systems making them promising candidates in the area of heterogeneous C-H functionalization, where efficient catalysts are still scarce.

Cobalt?NHC Catalyzed C(sp2)?C(sp3) and C(sp2)?C(sp2) Kumada Cross-Coupling of Aryl Tosylates with Alkyl and Aryl Grignard Reagents

The first cobalt-catalyzed cross-coupling of aryl tosylates with alkyl and aryl Grignard reagents is reported. The catalytic system uses CoF3 and NHCs (NHC=N-heterocyclic carbene) as ancillary ligands. The reaction proceeds via highly selective C?O bond functionalization, leading to the corresponding products in up to 98 % yield. The employment of alkyl Grignard reagents allows to achieve a rare C(sp2)?C(sp3) cross-coupling of C?O electrophiles, circumventing isomerization and β-hydride elimination problems. The use of aryl Grignards leads to the formation of biaryls. The C?O cross-coupling sets the stage for a sequential cross-coupling by exploiting the orthogonal selectivity of the catalytic system.

Amino-Induced 2D Cu-Based Metal–Organic Framework as an Efficient Heterogeneous Catalyst for Aerobic Oxidation of Olefins

With the assistance of hydrogen bonds of the o-amino group, we have successfully tuned a coordination structure from a metal–organic polyhedron (MOP) to a two-dimensional (2D) metal–organic framework (MOF). The amino group forms hydrogen bonds with the two vicinal carboxylic groups, and induces the ligand to coordinate with copper ions to form the 2D structure. The obtained 2D Cu-based MOF (Cu-AIA) has been applied as an efficient heterogeneous catalyst in the aerobic epoxidation of olefins by using air as oxygen source. Without the aggregation problem of active sites in MOPs, Cu-AIA possesses much higher reactivity than MOP-1. Furthermore, the amino group of the framework has been used as a modifiable site through post-synthetic metalation (PSMet) to prepare a 2D MOF-supported Pd single-site heterogeneous catalyst, which shows excellent catalytic performance for the Suzuki reaction. It indicates that Cu-AIA can also work as a good 2D MOF carrier for the derivation of other heterogeneous catalysts.

σ-Bond initiated generation of aryl radicals from aryl diazonium salts

σ-Bond nucleophiles and molecular oxygen transform aryl diazonium salts into aryl radicals. Experimental and computational studies show that Hantzsch esters transfer hydride to aryl diazonium species, and that oxygen initiates radical fragmentation of the diazene intermediate to produce aryl radicals. The operational simplicity of this addition-fragmentation process for the generation of aryl radicals, by a polar-radical crossover mechanism, has been illustrated in a variety of bond-forming reactions.

Catalytic Dehydrogenative Cyclization of o-Teraryls under pH-Neutral and Oxidant-Free Conditions

A cobaloxime-catalyzed acceptorless dehydrogenative cyclization of o-teraryls was developed. In stark contrast to the established methods such as the Scholl or Mallory reactions, this method does not require any strong acids or oxidants, and shows high atom economy and a broad substrate scope. It operates at near room temperature with light as the source of energy. Acid- or oxidant-sensitive functional groups, such as 4-methoxyphenyl, unprotected benzyl alcohol, silyl ether, and thiophene groups are tolerated. Remarkably, aryls with electron-withdrawing groups, and electron-poor heteroarenes, such as pyridine and pyrimidine, can also react. Preliminary mechanistic study reveals that hydrogen gas is released during the reaction, and both light and the cobalt catalyst are important for the dehydrogenation step.