190-24-9

Basic information

• Product Name: 1.12,2.3,4.5,6.7,8.9,10.11-HEXABENZOCORONENE
• Synonyms: Hexabenzo[bc:ef:hi:kl:no:qr]coronene;1.12,2.3,4.5,6.7,8.9,10.11-HEXABENZOCORONENE;Nsc91579;[bc,ef,hi,kl,no,qr]-Hexabenzocoronene
• CAS NO: 190-24-9
• Molecular Formula: C₄₂H₁₈
• Molecular Weight: 522.59
• Mol File: 190-24-9.mol
• Article Data: 9

Chemical Properties

• Melting Point: >600 °C
• Appearance: /
• Density: 1.633 g/cm³
• Refractive Index: 2.402
• CAS DataBase Reference: 1.12,2.3,4.5,6.7,8.9,10.11-HEXABENZOCORONENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1.12,2.3,4.5,6.7,8.9,10.11-HEXABENZOCORONENE(190-24-9)
• EPA Substance Registry System: 1.12,2.3,4.5,6.7,8.9,10.11-HEXABENZOCORONENE(190-24-9)

Safety Data

• Hazardous Substances Data: 190-24-9(Hazardous Substances Data)

Usage

General Description

1,12,2,3,4,5,6,7,8,9,10,11-hexabenzocoronene is a polycyclic aromatic hydrocarbon (PAH) composed of six hexagonal rings fused together with a total of 66 carbon atoms. It is a large, flat, aromatic molecule that exhibits high thermal stability and strong π-π interactions. 1,12,2,3,4,5,6,7,8,9,10,11-hexabenzocoronene has been studied for its potential applications in organic electronics, such as organic field-effect transistors, due to its excellent charge transport properties. It is also being investigated for its use in various optoelectronic devices, such as organic light-emitting diodes and photovoltaic cells, because of its strong fluorescence and high quantum yield. Furthermore, 1,12,2,3,4,5,6,7,8,9,10,11-hexabenzocoronene has shown promise for use in materials for energy storage and conversion technologies, such as in supercapacitors and lithium-ion batteries, due to its unique structure and electrical properties.

InChI:InChI=1/C42H18/c1-7-19-21-9-2-11-23-25-13-4-15-27-29-17-6-18-30-28-16-5-14-26-24-12-3-10-22-20(8-1)31(19)37-38(32(21)23)40(34(25)27)42(36(29)30)41(35(26)28)39(37)33(22)24/h1-18H

Synthetic route

1,2,3,4-tetraphenyltriphenylene (36262-81-4) → hexabenzocoronene (190-24-9)

Conditions	Yield
With iron(III) chloride In nitromethane; dichloromethane for 2h; Inert atmosphere;	99.8%

hexaphenylbenzene (992-04-1) → hexabenzocoronene (190-24-9)

Conditions	Yield
With iron(III) chloride In nitromethane; dichloromethane at 20℃; for 4h; Inert atmosphere;	95%
With tetrabutylammonium tetrafluoroborate; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 20℃; Electrolysis; Inert atmosphere; Schlenk technique;	95%
With iron(III) chloride In nitromethane; dichloromethane for 0.5h; Inert atmosphere;	93%

1,3,5-tris(2'-biphenyl)ylbenzene (16322-10-4) → hexabenzocoronene (190-24-9)

Conditions	Yield
With iron(III) chloride In nitromethane; dichloromethane for 1h;	80%

hexabenzo[a,cd,f,j,lm,o]perylene (190-22-7) → hexabenzocoronene (190-24-9)

Conditions	Yield
at 500℃; under 0.1 Torr;
With aluminium trichloride; sodium chloride at 120 - 130℃;
at 500℃; under 0.1 Torr;

8H-benzo[fg]naphthacene (196-03-2) → hexabenzocoronene (190-24-9)

Conditions	Yield
With sulfur at 320℃;

benzo[fg]naphthacen-8-one (86854-05-9) → hexabenzocoronene (190-24-9)

Conditions	Yield
With zinc(II) chloride; zinc at 330 - 350℃;

C42H36 → hexabenzocoronene (190-24-9) + dibenzo[fg,ij]phenanthro[9,10,1,2,3-pqrst]pentaphene (188-00-1)

Conditions	Yield
With copper at 400℃; for 1.5h;

9,18-Bis-(4-tert-butyl-phenyl)-1,2,3,4,5,6,7,8,9,10,11,12,13,14,15,16,17,18-octadecahydro-phenanthro[9,10-b]triphenylene-9,18-diol → hexabenzocoronene (190-24-9) + dibenzo[fg,ij]phenanthro[9,10,1,2,3-pqrst]pentaphene (188-00-1)

Conditions	Yield
With aluminium trichloride; copper; sodium chloride 1.) 120 deg C, 3 min; 2.) 400 deg C, 90 min; Yield given. Multistep reaction. Yields of byproduct given;

aluminium trichloride (7446-70-0) + hexabenzo[a,cd,f,j,lm,o]perylene (190-22-7) + NaCl → hexabenzocoronene (190-24-9)

Conditions	Yield
at 120 - 130℃;

hexaphenylbenzene (992-04-1) → C84H30 + hexabenzocoronene (190-24-9)

Conditions	Yield
With molybdenum(V) chloride In dichloromethane at 20℃; for 24h; Scholl reaction;

hexabenzocoronene (190-24-9) → C42Cl18

Conditions	Yield
With aluminum (III) chloride; Iodine monochloride In tetrachloromethane at 80℃; for 72h;	90%

hexabenzocoronene (190-24-9) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → C78H84B6O12

Conditions	Yield
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 3,4,7,8-Tetramethyl-o-phenanthrolin at 80℃; for 48h; Inert atmosphere; Schlenk technique;	27%

hexabenzocoronene (190-24-9) → C42H36

Conditions	Yield
With hydrogen; palladium on activated charcoal In tetrahydrofuran at 65℃; under 37503 - 45003.6 Torr; for 168000h;	10%

hexabenzocoronene (190-24-9) → pyrographite (7440-44-0)

Conditions	Yield
In solid heating the precursor in a sealed quartz ampules under vac. (1E-5 mbar) together with quartz plates at 400°C for 72 h, then at 800 or 650°C for 24 h; detected by mass-spectrometry;

Upstream product

• 992-04-1 hexaphenylbenzene 
• 190-22-7 hexabenzo[a,cd,f,j,lm,o]perylene 
• 196-03-2 8H-benzo[fg]naphthacene 
• 86854-05-9 benzo[fg]naphthacen-8-one 
• 7446-70-0 aluminium trichloride 
• 16322-10-4 3,5-di(2-biphenylyl)-o-terphenyl 
• 36262-81-4 1,2,3,4-tetraphenyltriphenylene 

Downstream Products

• 7440-44-0 pyrographite 

Relevant articles and documents

Synthesis and crystal packing of large polycyclic aromatic hydrocarbons: Hexabenzo[bc,ef,hi,kl,no,qr]coronene and dibenzo[fg,ij]phenanthro[9,10,1,2,3- pqrst]pentaphene

A detailed study of the oxidative cyclodehydrogenation of two oligophenylene precursors resulting in large polycyclic aromatic hydrocarbons (PAHs) which contain up to 42 carbon atoms gave insight into the reaction course. This study confirmed that the reaction occurs exclusively in an intramolecular fashion without the formation of organic side products. X-Ray diffraction, selected area electron diffraction, and low-dose high-resolution electron microscopy were used to analyse the effect of heat treatment and sublimation on the morphology and crystal structure of large PAHs, hexabenzo[bc,ef,hi,kl,no,qr]coronene (HBC) and dibenzo[fg,ij]phenanthro[9,10,1,2,3-pqrst]pentaphene (DBPP). HBC crystallizes in the γ-motif, as has been determined from single crystals previously. The experiments showed that small crystals exhibit some characteristic distortions of the unit cell. DBPP also crystallizes also in the γ-motif, but due to the 'double-bay area' in the periphery of the molecule channels with a diameter of about 4 A are formed in the crystal.

A slippery slope: Mechanistic analysis of the intramolecular scholl reaction of hexaphenylbenzene

DFT calculations support an arenium cation-based mechanism for the Scholl reaction converting hexaphenylbenzene to hexa-peri-benzocoronene. The curve connecting fully benzenoid intermediates on the potential energy diagram is convex. This "slippery slope" provides an explanation for the ease of this cascade Scholl reaction. The calculated reaction coordinate predicts that intermediates will not accumulate; this prediction is verified by experiment. Copyright

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.

Well-Defined Thiolated Nanographene as Hole-Transporting Material for Efficient and Stable Perovskite Solar Cells

Perovskite solar cells (PSCs) have been demonstrated as one of the most promising candidates for solar energy harvesting. Here, for the first time, a functionalized nanographene (perthiolated trisulfur-annulated hexa-peri-hexabenzocoronene, TSHBC) is employed as the hole transporting material (HTM) in PSCs to achieve efficient charge extraction from perovskite, yielding the best efficiency of 12.8% in pristine form. The efficiency is readily improved up to 14.0% by doping with graphene sheets into TSHBC to enhance the charge transfer. By the HOMO-LUMO level engineering of TSHBC homologues, we demonstrate that the HOMO levels are critical for the performance of PSCs. Moreover, beneficial from the hydrophobic nature of TSHBC, the devices show the improved stability under AM 1.5 illumination in the humidity about 45% without encapsulation. These findings open the opportunities for efficient HTMs based on the functionalized nanographenes utilizing the strong interactions of their functional groups with perovskite.