100516-61-8

Basic information

• Product Name: hexaethynylbenzene
• Synonyms: hexaethynylbenzene;1,2,3,4,5,6-Hexaethynylbenzene
• CAS NO: 100516-61-8
• Molecular Formula: C₁₈H₆
• Molecular Weight: 222.24024
• Mol File: 100516-61-8.mol

Chemical Properties

• Boiling Point: 382.4±42.0 °C(Predicted)
• Appearance: /
• Density: 1.14±0.1 g/cm3(Predicted)
• CAS DataBase Reference: hexaethynylbenzene(CAS DataBase Reference)
• NIST Chemistry Reference: hexaethynylbenzene(100516-61-8)
• EPA Substance Registry System: hexaethynylbenzene(100516-61-8)

Safety Data

• Hazardous Substances Data: 100516-61-8(Hazardous Substances Data)

Usage

Uses

Used in Materials Science:
Hexaethynylbenzene is utilized as a building block for the synthesis of novel materials due to its highly conjugated structure, which contributes to its electronic and optical characteristics. This makes it suitable for the development of advanced materials with specific properties tailored for various applications.
Used in Organic Electronics:
In the realm of organic electronics, hexaethynylbenzene serves as a component in the creation of organic semiconductors. Its electronic properties are leveraged to enhance the performance of devices such as organic light-emitting diodes (OLEDs), organic solar cells, and organic field-effect transistors (OFETs).
Used in Molecular Electronics:
Hexaethynylbenzene is employed as a molecular component in molecular electronics, where its unique structure and properties are harnessed to construct molecular-scale electronic devices. This includes the development of molecular wires and other nanoscale components that can be integrated into larger electronic systems.
Used in Nanotechnology:
In nanotechnology, hexaethynylbenzene is used as a precursor or building unit for the fabrication of nanostructures. Its properties are exploited to create nanomaterials with specific electronic, optical, or mechanical characteristics, which can be applied in various high-tech fields, including medicine, computing, and energy production.

Synthetic route

1,2,3,4,5,6-hexa(2-trimethylsilylethynyl)benzene (100516-62-9) → 1,2,3,4,5,6-hexaethynylbenzene (100516-61-8)

Conditions	Yield
With potassium fluoride In 1,2-dimethoxyethane at 0℃; for 2.5h;	99%
With potassium fluoride; 18-crown-6 ether In 1,2-dimethoxyethane at 23℃;
With potassium fluoride; 18-crown-6 ether In 1,2-dimethoxyethane at 23℃; for 0.5h; Hydrolysis;

2-Methyl-4-[pentakis-(3-hydroxy-3-methyl-but-1-ynyl)-phenyl]-but-3-yn-2-ol (70603-27-9) → 1,2,3,4,5,6-hexaethynylbenzene (100516-61-8)

Conditions	Yield
With potassium tert-butylate In tert-butyl alcohol

hexabromobenzene (87-82-1) + trimethylsilylacetylene (1066-54-2) → 1,2,3,4,5,6-hexaethynylbenzene (100516-61-8)

Conditions	Yield
With potassium fluoride; copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride; 18-crown-6 ether 1.) 100 deg C, 72 h; 2.) glyme, 10 min; Yield given. Multistep reaction;

1,2,3,4,5,6-hexaethynylbenzene (100516-61-8) → 1,2,3,4,5,6-hexa(2-chloroethynyl)benzene

Conditions	Yield
With N-chloro-succinimide; tetrabutyl-ammonium chloride; silver carbonate In acetonitrile at 20℃; for 12h;	63%

iodobenzene (591-50-4) + 1,2,3,4,5,6-hexaethynylbenzene (100516-61-8) → Hexakis(phenylethynyl)benzene (110846-75-8)

Conditions	Yield
With copper(l) iodide; triethylamine; bis(triphenylphosphane)palladium(II) In 1,2-dimethoxyethane at 60℃; for 68h; Sonogashira cross coupling;	41%

1,2,3,4,5,6-hexaethynylbenzene (100516-61-8) + Bis(trimethylsilyl)ethyne (14630-40-1) → 2,3,6,7,10,11-hexakis(trimethylsilyl)starphenylene (102234-00-4)

Conditions	Yield
dicarbonylcyclopentadienylcobalt for 19.5h; Heating;	39%

1,6-Bis(triisopropylsilyl)-1,3,5-hexatriyne (111409-80-4) + 1,2,3,4,5,6-hexaethynylbenzene (100516-61-8) → C90H132Si6

Conditions	Yield
cyclopentadienyl-biscarbonyl-cobalt(I) In toluene for 16h; Heating; Irradiation; Yield given;

1,2,3,4,5,6-hexaethynylbenzene (100516-61-8) + 2,5-dihydroxy-2,5-dimethyl-3-hexyne (142-30-3) → C42H48O6

Conditions	Yield
With dicarbonylcyclopentadienylcobalt In xylene for 8h; Cycloaddition; Heating; Irradiation;

1,2,3,4,5,6-hexaethynylbenzene (100516-61-8) + dihexyl 6-bromoazulene-1,3-dicarboxylate (501123-88-2) → hexakis[1,3-bis(hexyloxycarbonyl)-6-azulenylethynyl]benzene

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In tetrahydrofuran for 18h; Sonogashira-Hagihara coupling; Heating;	214 mg

1,2,3,4,5,6-hexaethynylbenzene (100516-61-8) + 4',5'-bis(butylthio)-4-iodotetrathiafulvalene (717918-81-5) → hexakis(4',5'-bis(butylthio)tetrathiafulvalenylethenyl)benzene

Conditions	Yield
With triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20℃; for 5h; Sonogashira coupling;	143 mg

4'-(4-iodo-2,6-dimethylphenyl)-2,2':6',2''-terpyridine (908563-58-6) + 1,2,3,4,5,6-hexaethynylbenzene (100516-61-8) → hexakis[3,5-dimethyl-1,4-(2,2':6',2''-terpyridine-4'-yl)phenylethynyl]benzene

Conditions	Yield
With copper(l) iodide; triethylamine; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; toluene at 20 - 80℃; for 48h; Sonogashira coupling;	262 mg

3,4,3',4'-tetrabutyl-5''-iodo-5-phenyl-[2,2';5',2'']terthiophene (1255382-94-5) + 1,2,3,4,5,6-hexaethynylbenzene (100516-61-8) → hexakis[2-(3',4',3'',4''-tetrabutyl-5''-phenyl-[5,2';5',2'']terthienyl)ethynyl]benzene (1255382-84-3)

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In tetrahydrofuran at 20℃; Sonogashira coupling;	175 mg

2-iodo-3-[(trimethylsilyl)ethynyl]naphthalene (1404452-60-3) + 1,2,3,4,5,6-hexaethynylbenzene (100516-61-8) → hexakis(2-{3-[(trimethylsilyl)ethynyl]naphthyl}ethynyl)benzene (1404452-61-4)

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In tetrahydrofuran at 45 - 80℃; for 65h; Sonogashira Cross-Coupling; Inert atmosphere;	36.2 mg

1-iodo-2-[(trimethylsilyl)ethynyl]naphthalene (1404452-66-9) + 1,2,3,4,5,6-hexaethynylbenzene (100516-61-8) → hexakis(1-{2-[(trimethylsilyl)ethynyl]naphthyl}ethynyl)benzene (1404452-64-7)

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In tetrahydrofuran at 45 - 85℃; for 120h; Sonogashira Cross-Coupling; Inert atmosphere;	92.3 mg

Upstream product

• 70603-27-9 2-Methyl-4-[pentakis-(3-hydroxy-3-methyl-but-1-ynyl)-phenyl]-but-3-yn-2-ol 
• 100516-62-9 1,2,3,4,5,6-hexa(2-trimethylsilylethynyl)benzene 
• 87-82-1 hexabromobenzene 
• 1066-54-2 trimethylsilylacetylene 

Downstream Products

• 110846-75-8 Hexakis(phenylethynyl)benzene 

Relevant articles and documents

Engineering the Coordination Environment of Single-Atom Platinum Anchored on Graphdiyne for Optimizing Electrocatalytic Hydrogen Evolution

Two Pt single-atom catalysts (SACs) of Pt-GDY1 and Pt-GDY2 were prepared on graphdiyne (GDY)supports. The isolated Pt atoms are dispersed on GDY through the coordination interactions between Pt atoms and alkynyl C atoms in GDY, with the formation of five-

Distinctive Improved Synthesis and Application Extensions Graphdiyne for Efficient Photocatalytic Hydrogen Evolution

Graphdiyne (GD), a novel two-dimension carbon hybrid material, due to its unique and excellent properties, has been widely concerned since this innovative material was successfully synthesized by Prof. Yuliang Li in 2010. Traditionally, its synthesis method is growing graphdiyne on copper foils or foam copper as a base catalytic material to deliver copper ions (Cu2+) under pyridine conditions. Here, an innovative progress for graphdiyne preparation approach of using Cu+ ion as a catalytic material is reported and its application in extending to the photocatalytic water-splitting to produce hydrogen in situ as well. In detail, by means of cuprous iodide used as a catalyst-carrier to grow a graphdiyne in a pyridine solution of monomeric hexynylbenzene and such CuI-graphdiyne composite catalyst is directly applied to photocatalytic hydrogen production in situ. Meanwhile, the hydrogen production of GD and CuI are 29.42 μmol/5 h and 156.49 μmol/5 h, respectively. In particular, the composite catalyst GD-CuI exhibits an optimum photo-catalytic hydrogen production activity (465.95 μmol/5 h) which is 15.8 times and 3.0 times that of pure GD and CuI respectively. This rational design, one-step construction of GD-CuI, successfully enhances photo-catalytic hydrogen evolution activity. The deeper characterization study results such as TEM, SEM, XPS, XRD, UV-vis DRS, Transient photocurrent and FT-IR etc. have been well researched and the results of which are in good agreement with each other.

Synthesis of Graphdiyne Nanowalls Using Acetylenic Coupling Reaction

Synthesizing graphdiyne with a well-defined structure is a great challenge. We reported herein a rational approach to synthesize graphdiyne nanowalls using a modified Glaser-Hay coupling reaction. Hexaethynylbenzene and copper plate were selected as monom

Graphdiyne oxides as excellent substrate for electroless deposition of Pd clusters with high catalytic activity

Graphdiyne (GDY), a novel kind of two-dimensional carbon allotrope consisting of sp- and sp2-hybridized carbon atoms, is found to be able to serve as the reducing agent and stabilizer for electroless deposition of highly dispersed Pd nanopartic

Towards technomimetic spoked wheels: Dynamic hexakis-heteroleptic coordination at a hexakis-terpyridine scaffold

The synthesis of hexakis-terpyridine 4 and an expedient approach to its dynamic hexakis-heteroleptic complexes are elaborated, the latter being readily accessible precursors for the construction of technomimetic molecular spoked wheels. The Royal Society

Hexagonally ordered nanostructures comprised of a flexible disk-like molecule with high self-assembling properties at neutral and cationic states

A novel amphiphilic TTF hexamer 1 with a flexible disk-like structure and strong self-aggregation properties has been synthesized. Nanowires fabricated from both 1 and its cation radical 1?+ in CHCl3/hexane solutions have a hexagonal

Improving the photo-cathodic properties of TiO2 nano-structures with graphdiynes

Graphdiyne (GD) nanoscale films were initially synthesised on copper foils and its oxide form, GD oxide (GDO) obtained by subsequent oxidation of purified GD. Hybrid nanocomposites of both GD and GDO with hydrothermally grown TiO2 nanorods were

Synthesis of Poly(6-azulenylethynyl)benzene Derivatives as a Multielectron Redox System with Liquid Crystalline Behavior

A series of poly(6-azulenylethynyl)benzenes substituted with n-hexyloxycarbonyl chains at 1,3-positions in azulene rings, i.e., hexakis-, 1,2,4,5-tetrakis-, 1,3,5-tris-, and 1,4-bis(6-azulenylethynyl)benzene derivatives 1, 2, 3, and 4b, have been prepared

Graphite diyne film and preparation method and application thereof

The invention relates to a graphite diyne film as well as a preparation method and application thereof. A precursor of the graphite diyne film is hexa(bromo-ethynyl) benzene. The method comprises the following steps: (1) injecting a solvent into a reactor filled with hexa(bromo-ethynyl) benzene and a copper-containing substrate; (2) dropwise adding an alkali solution into the reactor, stirring under the protection of an inert atmosphere, and carrying out a debromination coupling reaction; and (3) after the reaction is finished, generating a layer of black semitransparent film on the surface of the substrate, washing the surface of the substrate with acetone and N,N-dimethylformamide to obtain a black graphite diyne film which is applied to a catalytic material, an energy material or an electrode material. Compared with the prior art, the preparation method has the advantages that monomer molecules are more stable in air and higher in reaction activity, a coupling reaction can be stably and efficiently carried out, the reaction time is greatly shortened, the reaction can be carried out at room temperature, additional heating is not needed, energy can be greatly saved, and the problem of organic solvent volatilization caused by heating is solved.

Hierarchical Co3(PO4)2/CuI/g-CnH2n–2 S-Scheme Heterojunction for Efficient Photocatalytic Hydrogen Evolution

Graphdiyne (GD), a new type of carbon allotrope formed by sp and sp2 hybrid carbon atoms, has attracted wide attention due to its high π-conjugation degree, special band structure, and uniformly distributed pores. In traditional synthesis metho