36262-81-4

Upstream product

• 5660-91-3 1,3-diphenyl-2H-cyclopenta<1>phenanthren-2-one 
• 501-65-5 diphenyl acetylene 
• 10403-50-6 2,2'-Bis(phenylethynyl)<1,1'-biphenyl> 
• 36262-79-0 phenanthro[9,10-d][1,2,3]triazol-1-ylamine 
• 479-33-4 2,3,4,5-tetraphenylcyclopenta-2,4-dienone 
• 573-17-1 9-bromophenanthrene 

Downstream Products

• 190-24-9 hexabenzocoronene 

Relevant academic research and scientific papers

Preparation method for constructing hexabenzocoronene by utilizing polycyclic aromatic hydrocarbon phenanthrene in coal tar

The invention discloses a preparation method for constructing hexabenzocoronene by utilizing polycyclic aromatic hydrocarbon phenanthrene in coal tar. According to the method, polycyclic aromatic hydrocarbon phenanthrene in coal tar is used as a raw material and is subjected to an oxidation addition reaction with chromium trioxide to generate phenanthrenequinone, phenanthrenequinone and dibenzyl ketone are subjected to a nucleophilic addition elimination reaction in a potassium hydroxide methanol solution to generate 9, 10-phenanthro 1, 12-diphenyl cyclopentadiene ketone, 9, 10-phenanthro 1, 12-diphenyl cyclopentadiene ketone and diphenyl acetylene are subjected to a Diels-Alder cycloaddition reaction in a diphenyl ether solution to obtain 1, 2, 3, 4-tetraphenyl triphenylene, and finally,1, 2, 3, 4-tetraphenyl triphenylene and anhydrous ferric chloride are subjected to an oxidative cyclization dehydrogenation reaction to generate hexabenzocoronene. According to the invention, hexabenzocoronene is prepared by taking polycyclic aromatic hydrocarbon substance-phenanthrene in coal tar as a raw material. By reasonably planning the synthesis route, the yield of each step is increased, and the yield of hexabenzocoronene is increased. The method can be popularized and applied to the process of synthesizing graphene from other polycyclic aromatic hydrocarbons in the coal tar, so that high-added-value utilization of coal tar resources is improved.

Palladium-catalyzed annulation of 9-halophenanthrenes with alkynes: Synthesis, structural analysis, and properties of acephenanthrylene-based derivatives

The palladium-catalyzed annulation of 9-bromoand 9-chlorophenanthrenes with alkynes gave 4,5-disubstituted acephenanthrylenes in yields of 58-95% (9 examples). Asymmetric alkynes, such as 1-phenyl-1-propyne, 1-phenyl-1-hexyne, and 1-cyclopropyl-2-phenylethyne, regioselectively form (cyclo)alkyl-substituted products, following the regular rule that governs the carbopalladation of alkynes. This synthetic protocol can also be utilized in annulations with several p-extended bromoarenes, such as 7-bromo[5]helicene, 5-bromo[4]helicene, 9-bromoanthracene, 3-bromoperylene, and 3-bromofluoranthene, to give the corresponding annulated products in moderate to good yields (51-86%; 6 examples). Similarly, bromocorannulene produced highly curved 1,2-disubstituted cyclopentacorannulenes. Reactions of 6,12-dibromochrysene and 4,7-dibromo[4]helicene with di(4-tolyl) ethyne provided the twofold annulated products in moderate yields. 4,5-Diphenylacephenanthrylene and 6,7-diphenylbenzo[ a]acephenanthrylene thus generated were converted into phenanthro[9,10-e]acephenanthrylene and benzo[ a]phenanthro[9,10-e]acephenanthrylene, respectively, by oxidative cyclodehydrogenation. The structures of 4,5-diphenylacephenanthrylene, 4,5-diphenyldibenzo[a,l]acephenanthrylene, 1,2-diarylcyclopentacorannulenes, and benzo[ a]-phenanthro[9,10-e]acephenanthrylene were verified by X-ray crystallography. The photophysical and electrochemical properties of the selected annulated products were investigated.

Solvent free, phosphine free Pd-catalyzed annulations of aryl bromides with diarylacetylenes

Palladium nanoparticles and sodium acetate catalyze the reaction of aryl bromide with diarylacetylene to produce annulated products in good yield. One equivalent of PEG-600 serves as the solvent. This procedure is compatible with a wide variety of functional groups.

Palladium-catalyzed pentannulation of polycyclic aromatic hydrocarbons

We present a new and versatile one-step synthesis of a series of small molecular chromophores based on cyclopentannulated polycyclic aromatic hydrocarbons (PAH). Easily available pyrene, anthracene, and perylene bromides serve as starting materials for th

Palladium-catalyzed formation of highly substituted naphthalenes from arene and alkyne hydrocarbons

Several highly substituted naphthalenes 3 have been synthesized in a one-pot reaction by treatment of arenes 1 with alkynes 2 in the presence of palladium acetate and silver acetate. In this Pd-catalyzed protocol, an arene provides a benzo source for the construction of a naphthalene core through twofold aryl C - H bond activation. Reaction of triphenylphosphine with diphenylethyne (2 a) under the catalysis of PdIV complexes produced 1,2,3,4-tetraphenylnaphthalene (3ba) in 62% yield. Here, triphenylphosphine undergoes one aryl C - P bond cleavage and one aryl C - H bond activation to serve as a benzo moiety. Crystal structures of cycloadducts 3ea, 3ga, and 3ac have been analyzed. The twisted naphthalenes arise not only from the overcrowded substituents but also from the contribution of the CH3-π interaction.

Polycyclic Aromatic Compounds: Part VIII - A New Synthesis of Polycyclics Containing Phenanthrene Nucleus

A new series of polycyclic aromatic compounds with phenanthrene nucleus have been prepared.The method involves Diels Alder cycloaddition reaction of 1,3-diaryl-2H-cyclopentaphenanthren-2-one (I) with various dienophiles, viz. bicyclohepta-2,5-di