373596-08-8

Basic information

• Product Name: 6,13-Bis(triisopropylsilylethynyl)pentacene
• Synonyms: 6,13-Bis(triisopropylsilylethynyl)pentacene;6,13-Bis(triisopropylsilylethynyl)pentacene (This product is unavailable for selling domestically in U.S.);TIPS Pentacene;6,13-Bis(triisopropylsilylethynyl)pentacene (This product is unavailable in the U.S.);BIS(TIPSETHYNYL)PENTACENE;6,13-Bis(triisopropylsilylethynyl)pentacene >=99% (HPLC);Silane, (6,13-pentacenediyldi-2,1-ethynediyl)bis[tris(1-Methylethyl)- (9CI);6,13-bis[2-[tris(1-methylethyl)silyl]ethynyl]Pentacene
• CAS NO: 373596-08-8
• Molecular Formula: C₄₄H₅₄Si₂
• Molecular Weight: 639.07056
• Mol File: 373596-08-8.mol
• Article Data: 10

Chemical Properties

• Melting Point: 276℃
• Boiling Point: 695.255°C at 760 mmHg
• Flash Point: 337.688°C
• Appearance: /
• Density: 1.104 g/cm 3 at 25 °C
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.601
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: acetone: soluble0.16 wt. % at 23°C(lit.)
• CAS DataBase Reference: 6,13-Bis(triisopropylsilylethynyl)pentacene(CAS DataBase Reference)
• NIST Chemistry Reference: 6,13-Bis(triisopropylsilylethynyl)pentacene(373596-08-8)
• EPA Substance Registry System: 6,13-Bis(triisopropylsilylethynyl)pentacene(373596-08-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 373596-08-8(Hazardous Substances Data)

Usage

Applications

6,13-bis(triisopropylsilylethinyl)pentacene commonly known as TIPS pentacene. A high-purity TIPS-Pentacene for use in organic field-effect transistors (OFETs). TIPS-Pentacene is widely used as a high performance small molecule for OFET applications, with a mobility in excess of 1 cm2/Vs having being achieved in the literature. It has excellent solubility in a range of common organic solvents, and a good ambient stability - making it easy to process into devices.

Description

TIPS-Pentacene is tri-isopropylsilyly-ethynyl (TIPS) substituted pentacene at 6- and 13-positions of the conjugated core. The substituted TIPS functional groups extend the conjugation further to the branches to provide further stability, enhance solubility for solution processing?for low-cost and large-area fabrication of organic thin-film transistors (OTFTs).

Uses

Silyethyne-Substituted Pentacenes

General Description

6,13-Bis(triisopropylsilylethynyl)pentacene (TIPS-pentacene) is a conductive polymer that can form organic thin films for a variety of semiconductor applications due to its high charge carrier mobility and stability.

InChI:InChI=1/C44H54Si2/c1-29(2)45(30(3)4,31(5)6)23-21-39-41-25-35-17-13-15-19-37(35)27-43(41)40(22-24-46(32(7)8,33(9)10)34(11)12)44-28-38-20-16-14-18-36(38)26-42(39)44/h13-20,25-34H,1-12H3

Synthetic route

6,13-pentacenequinone (3029-32-1) + ((triisopropylsilyl)ethynyl)magnesium bromide (159862-82-5) → 6,13-bis[(triisopropylsilyl)ethynyl]pentacene (373596-08-8)

Conditions	Yield
Stage #1: 6,13-pentacenequinone; ((triisopropylsilyl)ethynyl)magnesium bromide In tetrahydrofuran at 60℃; Grignard reaction; Stage #2: With tin(ll) chloride In tetrahydrofuran at 60℃; Further stages.;	98%

6,13-pentacenequinone (3029-32-1) + tris-iso-propylsilyl acetylene (89343-06-6) → 6,13-bis[(triisopropylsilyl)ethynyl]pentacene (373596-08-8)

Conditions	Yield
Stage #1: tris-iso-propylsilyl acetylene With n-butyllithium In tetrahydrofuran at 20℃; for 0.666667h; Inert atmosphere; Stage #2: 6,13-pentacenequinone In tetrahydrofuran Inert atmosphere; Stage #3: With hydrogenchloride; tin(II) dichloride dihydrate In tetrahydrofuran; water for 7h; Inert atmosphere;	95%
Stage #1: tris-iso-propylsilyl acetylene With isopropylmagnesium chloride In tetrahydrofuran at 60℃; for 0.25h; Stage #2: 6,13-pentacenequinone In tetrahydrofuran for 0.5h; Heating; Further stages.;	82%
With n-butyllithium In tetrahydrofuran; hexane	63%
Stage #1: tris-iso-propylsilyl acetylene With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 0.333333h; Inert atmosphere; Stage #2: 6,13-pentacenequinone In tetrahydrofuran; hexane at -78 - 20℃; for 1.25h; Inert atmosphere; Stage #3: With hydrogenchloride; tin(II) chloride dihdyrate In tetrahydrofuran; hexane; water at 20℃; Inert atmosphere;	40%

6,13-bis[(triisopropylsilyl)ethynyl]-6,13-dihydroxypentacene-6,13H-diol → 6,13-bis[(triisopropylsilyl)ethynyl]pentacene (373596-08-8)

Conditions	Yield
With acetic acid; tin(ll) chloride at 20℃; for 24h;	9.5 g
With tin(II) chloride dihdyrate; sulfuric acid In water; acetone	Ca. 38 mg

C44H58O2Si2 → 6,13-bis[(triisopropylsilyl)ethynyl]pentacene (373596-08-8)

Conditions	Yield
With acetic acid; tin(ll) chloride at 25℃; for 2h; Inert atmosphere;
With sulfuric acid; tin(ll) chloride In tetrahydrofuran; hexane; water at -10℃; for 2h; Darkness;	151 mg

tris-iso-propylsilyl acetylene (89343-06-6) → 6,13-bis[(triisopropylsilyl)ethynyl]pentacene (373596-08-8)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: n-butyllithium / hexane / 0.67 h / 0 °C / Inert atmosphere 1.2: 0 - 20 °C / Inert atmosphere 2.1: tin(II) chloride dihdyrate; sulfuric acid / water; acetone View Scheme

C52H54Cl2N2O2Si2 → 6,13-bis[(triisopropylsilyl)ethynyl]pentacene (373596-08-8)

Conditions	Yield
With crithmene In toluene at 80℃; for 6h;

6,13-bis[(triisopropylsilyl)ethynyl]pentacene (373596-08-8) → C44H54O2Si2

Conditions	Yield
With oxygen; methylene blue In chloroform at -20℃; for 18h; Irradiation;	78%

tridecafluorotetradec-7-yne (1256917-96-0) + 6,13-bis[(triisopropylsilyl)ethynyl]pentacene (373596-08-8) → C72H54F52Si2 + C72H54F52Si2

Conditions	Yield
In 5,5-dimethyl-1,3-cyclohexadiene at 145℃; for 96h; Diels-Alder reaction; Inert atmosphere; optical yield given as %de;	A 74% B 12%

trans diiodobis(triethylphosphine)platinum(II) (35084-99-2, 15692-97-4, 15636-79-0) + 6,13-bis[(triisopropylsilyl)ethynyl]pentacene (373596-08-8) → [I(Et3P)2Pt]2-pentacenyl-6,13-diacetylide (1345693-13-1)

Conditions	Yield
With (C4H9)4NF; NH(CH(CH3)2)2; CuI In dichloromethane (N2); Pt complex, NH(CH(CH3)2)2, (C4H9)4NF, CuI and CH2Cl2 charged into a flask, a soln. of Si compd. added over 5 h, stirred overnight; evapd., chromd. (silica gel, hexane/CH2Cl2); elem. anal.;	71%

trans-(n-Bu3P)2PtI2 (15390-89-3) + 6,13-bis[(triisopropylsilyl)ethynyl]pentacene (373596-08-8) → [I(Bu3P)2Pt]2-pentacenyl-6,13-diacetylide (1345693-22-2)

Conditions	Yield
With (C4H9)4NF; NH(CH(CH3)2)2; CuI In dichloromethane (N2); Pt complex, NH(CH(CH3)2)2, (C4H9)4NF, CuI and CH2Cl2 charged into a flask, a soln. of Si compd. added over 5 h, stirred overnight; evapd., chromd. (silica gel, hexane/CH2Cl2); elem. anal.;	48%

PtI2(P(CH2CH2CH2CH3)3)2 (15390-89-3, 15390-94-0, 54832-25-6) + 6,13-bis[(triisopropylsilyl)ethynyl]pentacene (373596-08-8) → C74H120I2P4Pt2 (1345693-22-2)

Conditions	Yield
With copper(l) iodide; tetrabutyl ammonium fluoride; diisopropylamine In dichloromethane for 17h; Inert atmosphere; Schlenk technique;	48%

C70H120I2P4Pt2 + 6,13-bis[(triisopropylsilyl)ethynyl]pentacene (373596-08-8) → C140H186P4Pt2S2

Conditions	Yield
With copper(l) iodide; tetrabutyl ammonium fluoride; diisopropylamine In dichloromethane for 17h;	44%

dimethyl acetylenedicarboxylate (762-42-5) + 6,13-bis[(triisopropylsilyl)ethynyl]pentacene (373596-08-8) → anti-6,13-bis(triisopropylsilylethynyl)-5,7,12,14-tetrahydro-5,7,12,14-(1',2'-tetra(carbomethoxy))ethenopentacene + syn-6,13-bis(triisopropylsilylethynyl)-5,7,12,14-tetrahydro-5,7,12,14-(1',2'-tetra(carbomethoxy))ethenopentacene

Conditions	Yield
In xylene at 140℃; for 48h; Diels-Alder reaction;	A 40% B 38%

C70H120I2P4Pt2 + 6,13-bis[(triisopropylsilyl)ethynyl]pentacene (373596-08-8) → C105H153IP4Pt2S

Conditions	Yield
With copper(l) iodide; tetrabutyl ammonium fluoride; diisopropylamine In dichloromethane for 12h; Inert atmosphere; Schlenk technique;	19%

bis(pinacol)diborane (73183-34-3) + 6,13-bis[(triisopropylsilyl)ethynyl]pentacene (373596-08-8) → C88H104O4Si4

Conditions

Yield

Stage #1: bis(pinacol)diborane; 6,13-bis[(triisopropylsilyl)ethynyl]pentacene With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In cyclohexane for 20h; Schlenk technique; Inert atmosphere; Reflux; Stage #2: With dihydrogen peroxide; sodium hydroxide In tetrahydrofuran; water at 20℃; for 16h; Stage #3: With manganese(IV) oxide In dichloromethane at 20℃; for 35h;

6%

hexafluoro-2-butyne (692-50-2) + 6,13-bis[(triisopropylsilyl)ethynyl]pentacene (373596-08-8) → anti-6,13-bis(triisopropylsilylethynyl)-5,7,12,14-tetrahydro-5,7,12,14-(1',2'-tetra(trifluoromethyl))ethenopentacene + syn-6,13-bis(triisopropylsilylethynyl)-5,7,12,14-tetrahydro-5,7,12,14-(1',2'-tetra(trifluoromethyl))ethenopentacene

Conditions	Yield
In xylene at 100℃; for 24h; Diels-Alder reaction;	A 1.7 g B 0.8 g

6,13-bis[(triisopropylsilyl)ethynyl]pentacene (373596-08-8) → [(thiophenolato)(Et3P)2Pt]2-pentacenyl-6,13-diacetylide (1345693-14-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: (C4H9)4NF; NH(CH(CH3)2)2; CuI / dichloromethane 2: (C2H5)3N / dichloromethane View Scheme

6,13-bis[(triisopropylsilyl)ethynyl]pentacene (373596-08-8) → [(phenylacetylene(-1H))(Et3P)2Pt]2-pentacenyl-6,13-diacetylide (1345693-15-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: (C4H9)4NF; NH(CH(CH3)2)2; CuI / dichloromethane 2: CuI; (C2H5)3N / dichloromethane View Scheme

6,13-bis[(triisopropylsilyl)ethynyl]pentacene (373596-08-8) → [(pyridine)(Et3P)2Pt]2-pentacenyl-6,13-diacetylide-(OTf)2

Conditions	Yield
Multi-step reaction with 2 steps 1: (C4H9)4NF; NH(CH(CH3)2)2; CuI / dichloromethane 2: dichloromethane View Scheme

6,13-bis[(triisopropylsilyl)ethynyl]pentacene (373596-08-8) → [(2,6-xylyl isocyanide)(Et3P)2Pt]2-pentacenyl-6,13-diacetylide-(ClO4)2

Conditions	Yield
Multi-step reaction with 2 steps 1: (C4H9)4NF; NH(CH(CH3)2)2; CuI / dichloromethane 2: acetonitrile View Scheme

[RhCp*Cp]2 + 6,13-bis[(triisopropylsilyl)ethynyl]pentacene (373596-08-8) → C44H54Si2(1-)*C15H20Rh(1+)

Conditions	Yield
In benzene at 20℃; Kinetics; Glovebox;

bis(pinacol)diborane (73183-34-3) + 6,13-bis[(triisopropylsilyl)ethynyl]pentacene (373596-08-8) → 2,10-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-6,13-bis(triisopropylsilylethynyl)pentacene + 2,9-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-6,13-bis(triisopropylsilylethynyl)-pentacene

Conditions	Yield
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In cyclohexane for 20h; Schlenk technique; Inert atmosphere; Reflux; Overall yield = 61 %; Overall yield = 54.6 mg;

bis(pinacol)diborane (73183-34-3) + 6,13-bis[(triisopropylsilyl)ethynyl]pentacene (373596-08-8) → 2,9-dihydroxy-6,13-bis(triisopropylsilylethynyl)pentacene + 2,10-dihydroxy-6,13-bis(triisopropylsilylethynyl)pentacene

Conditions	Yield
Stage #1: bis(pinacol)diborane; 6,13-bis[(triisopropylsilyl)ethynyl]pentacene With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In cyclohexane for 20h; Schlenk technique; Inert atmosphere; Reflux; Stage #2: With dihydrogen peroxide; sodium hydroxide In tetrahydrofuran; water at 20℃; for 16h; Overall yield = 31 %; Overall yield = 47.5 mg;

fullerene-C60 (99685-96-8, 161105-99-3, 161106-00-9, 111138-12-6, 133318-63-5, 134053-11-5, 134931-35-4, 134931-36-5, 139703-76-7, 145633-27-8, 175414-73-0, 175414-74-1, 175414-75-2, 175519-12-7, 175519-13-8, 175519-14-9, 175519-15-0, 136376-46-0, 144906-37-6, 144906-38-7, 151767-00-9, 152882-97-8, 152882-98-9, 152882-99-0, 153062-34-1, 154171-74-1, 154171-75-2, 154333-99-0, 154334-00-6, 154397-63-4, 154460-59-0, 199456-56-9, 108739-25-9, 120329-57-9, 120329-58-0) + 6,13-bis[(triisopropylsilyl)ethynyl]pentacene (373596-08-8) → C104H54Si2

Conditions	Yield
With carbon disulfide at 65℃; for 24h;

tridecafluorotetradec-7-yne (1256917-96-0) + 6,13-bis[(triisopropylsilyl)ethynyl]pentacene (373596-08-8) → C72H54F52Si2

Conditions	Yield
In 5,5-dimethyl-1,3-cyclohexadiene for 96h; Inert atmosphere; Schlenk technique; Heating;

6,13-bis[(triisopropylsilyl)ethynyl]pentacene (373596-08-8) → C44H54Si2(1-)

Conditions	Yield
With (η5-pentamethylcyclopentadienyl)(η5-1,3,5-trimethylcyclohexa-1,3-dien-5-yl)ruthenium In tetrahydrofuran Solvent; Darkness;

Upstream product

• 89343-06-6 tris-iso-propylsilyl acetylene 
• 3029-32-1 6,13-pentacenequinone 
• 159862-82-5 ((triisopropylsilyl)ethynyl)magnesium bromide 

Downstream Products

• 1345693-15-3 [(phenylacetylene(-1H))(Et₃P)2Pt]2-pentacenyl-6,13-diacetylide 
• 1345693-14-2 [(thiophenolato)(Et₃P)2Pt]2-pentacenyl-6,13-diacetylide 

Relevant articles and documents

Functionalized pentacene: Improved electronic properties from control of solid-state order [20]

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High ionization potential conjugated polymers

We report the synthesis of a series of poly(p-phenylene ethynylene)s (PPEs) with high ionization potentials and associated high excited-state electron affinities. Their photophysical properties were investigated using steady-state and time-resolved fluorescence techniques. The ionization potentials of the polymer thin films were determined using ultraviolet photoelectron spectroscopy (UPS), and those with the highest ionization potentials displayed high sensitivity for the detection of electron-donating aromatic compounds. The effects of sterics, chemical structure, and electronic properties on the polymers' sensory responses were investigated by fluorescence quenching experiments in both solution and solid thin films. In addition, we report that in some cases the excited-state charge-transfer complexes (exciplexes) of the PPEs with analytes were observed. These latter effects provide promising opportunities for the formation of sensitive and selective chemical sensors.

Why triple bonds protect acenes from oxidation and decomposition

An experimental and computational study on the impact of functional groups on the oxidation stability of higher acenes is presented. We synthesized anthracenes, tetracenes, and pentacenes with various substituents at the periphery, identified their photooxygenation products, and measured the kinetics. Furthermore, the products obtained from thermolysis and the kinetics of the thermolysis are investigated. Density functional theory is applied in order to predict reaction energies, frontier molecular orbital interactions, and radical stabilization energies. The combined results allow us to describe the mechanisms of the oxidations and the subsequent thermolysis. We found that the alkynyl group not only enhances the oxidation stability of acenes but also protects the resulting endoperoxides from thermal decomposition. Additionally, such substituents increase the regioselectivity of the photooxygenation of tetracenes and pentacenes. For the first time, we oxidized alkynylpentacenes by using chemically generated singlet oxygen (1O2) without irradiation and identified a 6,13-endoperoxide as the sole regioisomer. The bimolecular rate constant of this oxidation amounts to only 1 × 10 5 s-1 M-1. This unexpectedly slow reaction is a result of a physical deactivation of 1O2. In contrast to unsubstituted or aryl-substituted acenes, photooxygenation of alkynyl-substituted acenes proceeds most likely by a concerted mechanism, while the thermolysis is well explained by the formation of radical intermediates. Our results should be important for the future design of oxidation stable acene-based semiconductors.

Application of zirconacyclopentadienes (metalla-heterocycles) and cross-coupling for the convenient preparative method of 6,13-disubstituted pentacene

Iodination of zirconacyclopentadiene derivative gave diiododiene derivative. The product was lithiated with t-BuLi and treated with diiodonaphthalene successively to afford 6,13-bis(trimethylsilyl)-5,14- dihydropentacene. A 6,13-diiodo-5,14-dihydropentacene was synthesized by iodination of 6,13-bis(trimethylsilyl)-5,14-dihydropentacene with ICl. This diiododihydropentacene was used for the introduction of substituent at 6 and 13 positions by the cross-coupling reactions with Pd catalyst. After aromatization by a combination of DDQ and γ-terpinene or triethylamine, 6,13-disubstituted pentacene derivatives were synthesized.