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135-48-8

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135-48-8 Usage

Description

Pentacene is an acene with flat-like molecules made of five linearly-fused benzene rings, known for its large carrier mobilities and extensive study as a p-type semiconductor in organic field-effect transistors.

Uses

Used in Electronics Industry:
Pentacene is used as a p-type semiconductor in organic field-effect transistors for its large carrier mobilities of about 1 cm2/V s within the plane parallel to the substrate.
Used in Solar Energy Industry:
Pentacene is used in heterojunction solar cells with C60, achieving a power conversion efficiency over 2.7%, due to its large carrier mobilities.
Used in Lighting Industry:
Pentacene is used in light-emitting diode applications, taking advantage of its semiconductor properties.
Used in Wastewater Treatment Industry:
Pentacene is found in wastewater treatment facility units, although the specific application is not detailed in the provided materials.

Purification Methods

It forms blue crystals from *benzene or nitrobenzene and sublimes in a vacuum. [Clar & John Ber 62 940 1929, 64 981 1931, Beilstein 5 IV 2721.]

Check Digit Verification of cas no

The CAS Registry Mumber 135-48-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,3 and 5 respectively; the second part has 2 digits, 4 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 135-48:
(5*1)+(4*3)+(3*5)+(2*4)+(1*8)=48
48 % 10 = 8
So 135-48-8 is a valid CAS Registry Number.
InChI:InChI=1/C22H14/c1-2-6-16-10-20-14-22-12-18-8-4-3-7-17(18)11-21(22)13-19(20)9-15(16)5-1/h1-14H

135-48-8 Well-known Company Product Price

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  • Detail
  • Alfa Aesar

  • (H56310)  Pentacene, 97%   

  • 135-48-8

  • 250mg

  • 1492.0CNY

  • Detail
  • Alfa Aesar

  • (H56310)  Pentacene, 97%   

  • 135-48-8

  • 1g

  • 3570.0CNY

  • Detail
  • Sigma-Aldrich

  • (45797)  Pentacene  analytical standard

  • 135-48-8

  • 45797-100MG

  • 1,800.63CNY

  • Detail
  • Aldrich

  • (698423)  Pentacene  triple-sublimed grade, ≥99.995% trace metals basis

  • 135-48-8

  • 698423-500MG

  • 5,201.82CNY

  • Detail
  • Aldrich

  • (684848)  Pentacene  sublimed grade, ≥99.9% trace metals basis

  • 135-48-8

  • 684848-1G

  • 5,812.56CNY

  • Detail
  • Aldrich

  • (P1802)  Pentacene  99%

  • 135-48-8

  • P1802-100MG

  • 671.58CNY

  • Detail
  • Aldrich

  • (P1802)  Pentacene  99%

  • 135-48-8

  • P1802-1G

  • 4,265.82CNY

  • Detail
  • Aldrich

  • (P1802)  Pentacene  99%

  • 135-48-8

  • P1802-5G

  • 13,536.90CNY

  • Detail

135-48-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name pentacene

1.2 Other means of identification

Product number -
Other names Pentacene

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:135-48-8 SDS

135-48-8Synthetic route

6,13-dihydro-6,13-epithiomethanopentacen-16-one
783321-43-7

6,13-dihydro-6,13-epithiomethanopentacen-16-one

pentacene
135-48-8

pentacene

Conditions
ConditionsYield
at 220℃; UV-irradiation;100%
6,13-dihydro-6,13-ethanopentacene-15,16-dione

6,13-dihydro-6,13-ethanopentacene-15,16-dione

pentacene
135-48-8

pentacene

Conditions
ConditionsYield
In chloroform at 20℃; Irradiation;96%
In toluene at 20℃; Irradiation;74%
In toluene UV-irradiation;
Neat (no solvent); Irradiation using laser light;
for 0.0833333h; Neat (no solvent); Irradiation using xenon lamp;
6,13-dihydro-6,13-dihydroxypentacene

6,13-dihydro-6,13-dihydroxypentacene

pentacene
135-48-8

pentacene

Conditions
ConditionsYield
With hydrogenchloride; tin(ll) chloride In water; N,N-dimethyl-formamide at 0℃; for 0.0291667h; Darkness;93%
With hydrogenchloride In tetrahydrofuran at -50℃; for 0.25h; Inert atmosphere; Reflux;
5,14-dihydro-pentacene
20244-36-4

5,14-dihydro-pentacene

pentacene
135-48-8

pentacene

Conditions
ConditionsYield
palladium on activated charcoal In xylene for 72h; Heating;92%
2,2'-(1,3-phenylenebis(methylene))dibenzaldehyde

2,2'-(1,3-phenylenebis(methylene))dibenzaldehyde

pentacene
135-48-8

pentacene

Conditions
ConditionsYield
With trifluoroacetic acid at 20℃; for 5h;83%
6,13-pentacenequinone
3029-32-1

6,13-pentacenequinone

pentacene
135-48-8

pentacene

Conditions
ConditionsYield
Stage #1: 6,13-pentacenequinone With sodium tetrahydroborate; water In tetrahydrofuran at 0 - 60℃; for 2h;
Stage #2: With hydrogenchloride; tin(II) chloride dihdyrate In N,N-dimethyl-formamide at 0℃; for 0.0208333h; Darkness;
79%
Multistep reaction.;54%
With lithium aluminium tetrahydride In tetrahydrofuran for 0.5h; Inert atmosphere; Cooling with ice;54%
With oxidizing agent; diborane 1.) diglyme; Multistep reaction;
Multi-step reaction with 2 steps
1: 70 percent / KBH4 / methanol / several d
2: 67 percent / KI, sodium hyposulfite / acetic acid / 3 h / Heating
View Scheme
dihydroxy-6,13 dihydro-6,13 pentacene cis
76727-08-7

dihydroxy-6,13 dihydro-6,13 pentacene cis

pentacene
135-48-8

pentacene

Conditions
ConditionsYield
With sodium thiosulfate; potassium iodide In acetic acid for 3h; Heating;67%
6,13-dihydro-14-hydroxy-6,13-ethenopentacene
104942-18-9

6,13-dihydro-14-hydroxy-6,13-ethenopentacene

pentacene
135-48-8

pentacene

Conditions
ConditionsYield
With 1,2,4,5-tetrazine-3,6-dicarboxylic acid dimethyl ester In dipentyl ether for 0.025h; Reflux;48%
3,6-di(2'-pyridyl)-1,2,4,5-tetrazine
1671-87-0

3,6-di(2'-pyridyl)-1,2,4,5-tetrazine

6,13-dihydro-14-hydroxy-6,13-ethenopentacene
104942-18-9

6,13-dihydro-14-hydroxy-6,13-ethenopentacene

A

pentacene
135-48-8

pentacene

B

6,13-dihydro-6,13-[4',5']-3',6'-(di-2
1370025-49-2

6,13-dihydro-6,13-[4',5']-3',6'-(di-2"-pyridyl)pyridazinopentacene

C

3,6-di(pyridin-2'-yl)-s-tetrazine
36901-11-8

3,6-di(pyridin-2'-yl)-s-tetrazine

D

3,6-di(pyridin-2-yl)-1,4-dihydro-1,2,4,5-tetrazine
1671-86-9

3,6-di(pyridin-2-yl)-1,4-dihydro-1,2,4,5-tetrazine

Conditions
ConditionsYield
In dipentyl ether for 2h; Diels-Alder-retro-Diels-Alder; Reflux;A 28%
B n/a
C n/a
D n/a
1H-cyclopropa[b]naphthalene
286-85-1

1H-cyclopropa[b]naphthalene

A

6,13-dihydropentacene
13579-08-3

6,13-dihydropentacene

B

1,2-bis(2-naphthyl)ethane
21969-45-9

1,2-bis(2-naphthyl)ethane

C

pentacene
135-48-8

pentacene

D

6,7-dihydropentaphene
112223-66-2

6,7-dihydropentaphene

E

2-Methylnaphthalene
91-57-6

2-Methylnaphthalene

Conditions
ConditionsYield
With potassium sand; cadmium(II) chloride In tetrahydrofuran at -40 - 0℃; Product distribution; Mechanism; multistep reaction; further temperatures, further metal surface;A 2%
B 2%
C 2%
D 4%
E 24%
6,13-dihydro-6,13-methanopentacene-15-one
904913-36-6

6,13-dihydro-6,13-methanopentacene-15-one

pentacene
135-48-8

pentacene

Conditions
ConditionsYield
In tetrahydrofuran Photolysis;16.2%
at 150 - 160℃; for 1h;
at -268.16℃; for 0.25h; UV-irradiation;
5,14-dihydro-5,14-methanopentacen-15-one
1037314-15-0

5,14-dihydro-5,14-methanopentacen-15-one

pentacene
135-48-8

pentacene

Conditions
ConditionsYield
In tetrahydrofuran Temperature; Wavelength; Photolysis;16.2%
In tetrahydrofuran UV-irradiation;
6,13-dihydropentacene
13579-08-3

6,13-dihydropentacene

pentacene
135-48-8

pentacene

Conditions
ConditionsYield
With nitrobenzene; 9,10-phenanthrenequinone
With chloranil; xylene
With copper at 380℃; under 12 - 20 Torr;
Δ4a(14a),7a(11a)-octadecahydro-pentacene

Δ4a(14a),7a(11a)-octadecahydro-pentacene

pentacene
135-48-8

pentacene

Conditions
ConditionsYield
With palladium on activated charcoal at 245℃;
tetrachloromethane
56-23-5

tetrachloromethane

6,13-dihydropentacene
13579-08-3

6,13-dihydropentacene

chloranil
118-75-2

chloranil

pentacene
135-48-8

pentacene

15r.16c.18.19-tetrachloro-17.20-dioxo-6.13.15.16.17.20-hexahydro-6.13-o-benzeno-pentacene
859943-68-3

15r.16c.18.19-tetrachloro-17.20-dioxo-6.13.15.16.17.20-hexahydro-6.13-o-benzeno-pentacene

nitrobenzene
98-95-3

nitrobenzene

A

pentacene
135-48-8

pentacene

B

chloranil
118-75-2

chloranil

6,13-dihydropentacene
13579-08-3

6,13-dihydropentacene

nitrobenzene
98-95-3

nitrobenzene

9,10-phenanthrenequinone
84-11-7

9,10-phenanthrenequinone

pentacene
135-48-8

pentacene

5,14:7,12-diepoxy-5,7,12,14-tetrahydro-5,7,12,14-tetrakis(trimethylsilyl)pentacene
100790-90-7, 100895-73-6

5,14:7,12-diepoxy-5,7,12,14-tetrahydro-5,7,12,14-tetrakis(trimethylsilyl)pentacene

pentacene
135-48-8

pentacene

Conditions
ConditionsYield
With lithium aluminium tetrahydride; trifluoroacetic acid 1.) benzene, 3 h, 2.) THF, RT, 2 h; Multistep reaction;
1H-cyclopropa[b]naphthalene
286-85-1

1H-cyclopropa[b]naphthalene

A

6,13-dihydropentacene
13579-08-3

6,13-dihydropentacene

B

1,2-bis(2-naphthyl)ethane
21969-45-9

1,2-bis(2-naphthyl)ethane

C

pentacene
135-48-8

pentacene

D

6,7-dihydropentaphene
112223-66-2

6,7-dihydropentaphene

Conditions
ConditionsYield
With potassium mirror; cadmium(II) chloride 1.) THF, 0 deg C, 30 min; r.t., 45 min, 2.) THF, reflux, overnight; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;
With potassium mirror; cadmium(II) chloride 1.) THF, 0 deg C, 30 min; r.t., 45 min, 2.) THF, reflux, overnight; Multistep reaction. Further byproducts given. Yields of byproduct given;
With potassium sand; cadmium(II) chloride 1.) THF, -40 deg C, 50 min, 2.) THF, r.t., overnight; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;
1,5-dibenzoyl-2,4-dimethyl-benzene
57878-28-1

1,5-dibenzoyl-2,4-dimethyl-benzene

A

6,13-dihydropentacene
13579-08-3

6,13-dihydropentacene

B

pentacene
135-48-8

pentacene

C

2-methylanthracene
613-12-7

2-methylanthracene

D

hydrocarbon C22H16

hydrocarbon C22H16

Conditions
ConditionsYield
Pyrolysis;
5-benzyl-2,4-dimethyl-benzophenone
860563-90-2

5-benzyl-2,4-dimethyl-benzophenone

copper-powder

copper-powder

A

pentacene
135-48-8

pentacene

B

pentaphene
222-93-5

pentaphene

Conditions
ConditionsYield
Erhitzen des Reaktionsprodukts mit Chloranil in Xylol;
C24H17NO2S

C24H17NO2S

pentacene
135-48-8

pentacene

Conditions
ConditionsYield
retro Diels-Alder reaction; Heating;
7,14-dihydropentacene-5,12-dione
504423-06-7

7,14-dihydropentacene-5,12-dione

pentacene-5,7(12H,14H)-dione
504423-07-8

pentacene-5,7(12H,14H)-dione

diethylene glycol dimethyl ether
111-96-6

diethylene glycol dimethyl ether

pentacene
135-48-8

pentacene

Conditions
ConditionsYield
With hydrogenchloride; sodium borohydrid; acetic acid In methanol; water
pentacene-5,7,12,14-tetraone
23912-79-0

pentacene-5,7,12,14-tetraone

aluminum tri-sec-butoxide
2269-22-9

aluminum tri-sec-butoxide

pentacene
135-48-8

pentacene

Conditions
ConditionsYield
In cyclohexanol
6,13-dihydro-6,13-methano-15-tert-butoxypentacene
942262-46-6

6,13-dihydro-6,13-methano-15-tert-butoxypentacene

pentacene
135-48-8

pentacene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 83 percent / sulfuric acid; H2O / tetrahydrofuran / 48 h / 20 °C
2: 60 percent / triethylamine; sulfur trioxide/pyridine / CH2Cl2; dimethylsulfoxide / 12.5 h / 20 °C
3: 1 h / 150 - 160 °C
View Scheme
6,13-dihydro-6,13-methano-15-hydroxypentacene
942262-51-3

6,13-dihydro-6,13-methano-15-hydroxypentacene

pentacene
135-48-8

pentacene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 60 percent / triethylamine; sulfur trioxide/pyridine / CH2Cl2; dimethylsulfoxide / 12.5 h / 20 °C
2: 1 h / 150 - 160 °C
View Scheme
6,13-dihydro-6,13-ethenopentacene

6,13-dihydro-6,13-ethenopentacene

pentacene
135-48-8

pentacene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 98 percent / N-methylmorpholine-N-oxide*2H2O; OsO4 / 2-methyl-propan-2-ol; acetone / 32 h / 20 °C
2: 43 percent / trifluoroacetic anhydride; DMSO / CH2Cl2 / -60 - 20 °C
3: toluene / UV-irradiation
View Scheme
6,13-dihydro-15,17-dihydroxy-6,13-ethanopentacene

6,13-dihydro-15,17-dihydroxy-6,13-ethanopentacene

pentacene
135-48-8

pentacene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 43 percent / trifluoroacetic anhydride; DMSO / CH2Cl2 / -60 - 20 °C
2: toluene / UV-irradiation
View Scheme
anthranilic acid
118-92-3

anthranilic acid

1-chloro-4-methyl-thioxanthone

1-chloro-4-methyl-thioxanthone

pentacene
135-48-8

pentacene

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: isoamyl nitrite / tetrahydrofuran / 2 h / Heating
1.2: 71 percent / DDQ / CHCl3 / 2 h / 20 °C
2.1: 98 percent / N-methylmorpholine-N-oxide*2H2O; OsO4 / 2-methyl-propan-2-ol; acetone / 32 h / 20 °C
3.1: 43 percent / trifluoroacetic anhydride; DMSO / CH2Cl2 / -60 - 20 °C
4.1: toluene / UV-irradiation
View Scheme
pentacene
135-48-8

pentacene

N-(2'-methyl-4-nitrophenyl)maleimide

N-(2'-methyl-4-nitrophenyl)maleimide

C33H22N2O4

C33H22N2O4

Conditions
ConditionsYield
In toluene at 100℃; Diels-Alder Cycloaddition; Sealed tube;100%
pentacene
135-48-8

pentacene

1-Phenylbut-1-en-3-one
122-57-6

1-Phenylbut-1-en-3-one

C32H24O

C32H24O

Conditions
ConditionsYield
With bromo-triphenyl-methane; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In 1,2-dichloro-ethane at 50℃; for 24h; Diels-Alder Cycloaddition; diastereoselective reaction;99%
pentacene
135-48-8

pentacene

benzalacetophenone
94-41-7

benzalacetophenone

C37H26O

C37H26O

Conditions
ConditionsYield
With bromo-triphenyl-methane; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In 1,2-dichloro-ethane at 50℃; for 24h; Diels-Alder Cycloaddition; diastereoselective reaction;99%
pentacene
135-48-8

pentacene

N-[(1S,2R)-1-methyl-2-phenyl-2-hydroxyethyl]maleimide
587055-89-8

N-[(1S,2R)-1-methyl-2-phenyl-2-hydroxyethyl]maleimide

N-[(1S,2R)-1-methyl-2-phenyl-2-hydroxyethyl]-4,11[2',3']naphtho-3a,4,11,11a-tetrahydro-1H-naphtho[2,3-f]isoindole-1,3(2H)-dione

N-[(1S,2R)-1-methyl-2-phenyl-2-hydroxyethyl]-4,11[2',3']naphtho-3a,4,11,11a-tetrahydro-1H-naphtho[2,3-f]isoindole-1,3(2H)-dione

Conditions
ConditionsYield
In xylene at 130℃; for 48h; Diels-Alder addition;98%
pentacene
135-48-8

pentacene

C11H9FO3
105507-76-4

C11H9FO3

C33H23FO3

C33H23FO3

Conditions
ConditionsYield
With bromo-triphenyl-methane; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In 1,2-dichloro-ethane at 50℃; for 24h; Diels-Alder Cycloaddition; diastereoselective reaction;96%
pentacene
135-48-8

pentacene

Methyl-p-chlorbenzylidenpyruvat
42393-11-3, 97897-42-2

Methyl-p-chlorbenzylidenpyruvat

C33H23ClO3

C33H23ClO3

Conditions
ConditionsYield
With bromo-triphenyl-methane; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In 1,2-dichloro-ethane at 50℃; for 24h; Diels-Alder Cycloaddition; diastereoselective reaction;95%
pentacene
135-48-8

pentacene

Methyl-3,4-dichlorbenzylidenpyruvat
42393-13-5

Methyl-3,4-dichlorbenzylidenpyruvat

C33H22Cl2O3

C33H22Cl2O3

Conditions
ConditionsYield
With bromo-triphenyl-methane; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In 1,2-dichloro-ethane at 50℃; for 24h; Diels-Alder Cycloaddition; diastereoselective reaction;94%
4-(4-bromophenyl)-2-oxo-3-butenoic acid methyl ester
104093-34-7

4-(4-bromophenyl)-2-oxo-3-butenoic acid methyl ester

pentacene
135-48-8

pentacene

C33H23BrO3

C33H23BrO3

Conditions
ConditionsYield
With bromo-triphenyl-methane; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In 1,2-dichloro-ethane at 50℃; for 24h; Diels-Alder Cycloaddition; diastereoselective reaction;93%
pentacene
135-48-8

pentacene

epidioxy-6,13 dihydro-6,13 pentacene
7258-98-2

epidioxy-6,13 dihydro-6,13 pentacene

Conditions
ConditionsYield
With potassium dichromate; hematoporphyrin chlorohydrate In ethanol; chloroform; water for 4h; Irradiation;92%
pentacene
135-48-8

pentacene

C11H9FO3
1210054-89-9

C11H9FO3

C33H23FO3

C33H23FO3

Conditions
ConditionsYield
With bromo-triphenyl-methane; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In 1,2-dichloro-ethane at 50℃; for 24h; Diels-Alder Cycloaddition; diastereoselective reaction;92%
pentacene
135-48-8

pentacene

methyl 4-phenyl-2-oxo-3-butenoate
107969-78-8, 6395-86-4

methyl 4-phenyl-2-oxo-3-butenoate

C33H24O3

C33H24O3

Conditions
ConditionsYield
With bromo-triphenyl-methane; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In 1,2-dichloro-ethane at 50℃; for 24h; Diels-Alder Cycloaddition; diastereoselective reaction;91%
N-sulphinylacetamide
16767-75-2

N-sulphinylacetamide

pentacene
135-48-8

pentacene

C24H17NO2S

C24H17NO2S

Conditions
ConditionsYield
With methyltrioxorhenium(VII) In chloroform Heating;90%
pentacene
135-48-8

pentacene

methyl (phenylmethylidene)pyruvate
100518-76-1

methyl (phenylmethylidene)pyruvate

C34H26O3

C34H26O3

Conditions
ConditionsYield
With bromo-triphenyl-methane; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In 1,2-dichloro-ethane at 50℃; for 24h; Diels-Alder Cycloaddition; diastereoselective reaction;89%
pentacene
135-48-8

pentacene

C15H12O3
1201664-47-2

C15H12O3

C37H26O3

C37H26O3

Conditions
ConditionsYield
With bromo-triphenyl-methane; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In 1,2-dichloro-ethane at 50℃; for 24h; Diels-Alder Cycloaddition; diastereoselective reaction;89%
vinylene carbonate
872-36-6

vinylene carbonate

pentacene
135-48-8

pentacene

C25H16O3

C25H16O3

Conditions
ConditionsYield
In xylene at 180℃; for 72h; Diels-Alder reaction;88%
In xylene at 170℃; Diels-Alder reaction;80%
pentacene
135-48-8

pentacene

5,15-bis(4′-methoxyphenyl)porphyrin
128374-11-8

5,15-bis(4′-methoxyphenyl)porphyrin

C56H40N4O2

C56H40N4O2

Conditions
ConditionsYield
In various solvent(s) at 200℃; Addition;87%
pentacene
135-48-8

pentacene

1-(4-Methoxy-2-methyl-phenyl)-pyrrole-2,5-dione

1-(4-Methoxy-2-methyl-phenyl)-pyrrole-2,5-dione

C34H25NO3

C34H25NO3

Conditions
ConditionsYield
In toluene at 100℃; for 5h; Diels-Alder Cycloaddition; Sealed tube; Inert atmosphere;84%
C11H9FO3
960382-66-5

C11H9FO3

pentacene
135-48-8

pentacene

C33H23FO3

C33H23FO3

Conditions
ConditionsYield
With bromo-triphenyl-methane; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In 1,2-dichloro-ethane at 50℃; for 24h; Diels-Alder Cycloaddition; diastereoselective reaction;84%
trans-Crotonaldehyde
123-73-9

trans-Crotonaldehyde

pentacene
135-48-8

pentacene

C26H20O

C26H20O

Conditions
ConditionsYield
With bromo-triphenyl-methane; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In 1,2-dichloro-ethane at 50℃; for 24h; Diels-Alder Cycloaddition; diastereoselective reaction;84%
pentacene
135-48-8

pentacene

tetrakis(pentafluorophenyl)porphyrin
25440-14-6

tetrakis(pentafluorophenyl)porphyrin

C66H24F20N4

C66H24F20N4

Conditions
ConditionsYield
In various solvent(s) at 200℃; Diels-Alder reaction; microwave irradiation;83%
In various solvent(s) at 200℃; Addition;60%
pentacene
135-48-8

pentacene

ethenetetracarbonitrile
670-54-2

ethenetetracarbonitrile

C28H14N4

C28H14N4

Conditions
ConditionsYield
In toluene at 100℃; for 3h; Diels-Alder reaction; Inert atmosphere;82%
N-(2,4-dimethyl-phenyl)-maleimide
1080-52-0

N-(2,4-dimethyl-phenyl)-maleimide

pentacene
135-48-8

pentacene

C34H25NO2

C34H25NO2

Conditions
ConditionsYield
In toluene at 100℃; for 5h; Diels-Alder Cycloaddition; Sealed tube; Inert atmosphere;81%
pentacene
135-48-8

pentacene

C13H8F3NO4

C13H8F3NO4

C35H22F3NO4

C35H22F3NO4

Conditions
ConditionsYield
In toluene for 12h; Diels-Alder Cycloaddition; Reflux;80%
pentacene
135-48-8

pentacene

4-Biphenyliden-2-keto-propionsaeuremethylester
68968-90-1

4-Biphenyliden-2-keto-propionsaeuremethylester

C39H28O3

C39H28O3

Conditions
ConditionsYield
With bromo-triphenyl-methane; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In 1,2-dichloro-ethane at 50℃; for 24h; Diels-Alder Cycloaddition; diastereoselective reaction;79%

135-48-8Related news

Quantum Master Equation Approach to Singlet Fission Dynamics in Pentacene (cas 135-48-8) Linear Aggregate Models: Size Dependences of Excitonic Coupling Effects09/30/2019

The singlet fission (SF) dynamics of pentacene linear aggregate models are investigated using the quantum master equation method by focusing on the Frenkel excitonic (FE) coupling effects on the SF rate and double triplet (TT) yield as well as on their aggregate size dependences. It is found tha...detailed

BN‐Embedded TetrabenzoPentacene (cas 135-48-8): A Pentacene (cas 135-48-8) Derivative with Improved Stability09/29/2019

Considerable efforts have been devoted to achieving stable acene derivatives for electronic applications; however, the instability is still a major issue for such derivatives. To achieve higher stability with minimum structural change, CC units in the acenes were replaced with isoelectronic BN u...detailed

135-48-8Relevant articles and documents

Photochemical synthesis of pentacene and its derivatives

Yamada, Hiroko,Yamashita, Yuko,Kikuchi, Makoto,Watanabe, Hikaru,Okujima, Tetsuo,Uno, Hidemitsu,Ogawa, Takuji,Ohara, Keishi,Ono, Noboru

, p. 6212 - 6220 (2005)

A novel α-diketone precursor of pentacene, 6,13-dihydro-6,13- ethanopentacene-15, 16-dione, was prepared and converted successfully to pentacene in 74% yield by photolysis of the precursor in toluene: Irradiation of the diketone solution in toluene with light of 460 nm under an Ar atmosphere caused the solution to change from yellow to fluorescent orange-pink within a few minutes, after which, purple precipitates appeared. After 35 min, the solution changed to colorless and the purple precipitates were filtered to give pentacene in 74% yield. By contrast, in the presence of oxygen, the color of the solution changed from yellow to pale yellow, and only 6,13-endoperoxide of pentacene was quantitatively obtained. The rate of the reaction upon photolysis was measured by observing the decay of n-π* absorption of the precursor at 460 nm, and was found to be similar in both the presence and absence of oxygen. Therefore, the photoreaction of the α-diketone precursor seemed to occur via the singlet excited state. Because the T-T absorption of pentacene was observed upon photolysis of the precursor in the nanosecond transient absorption measurement under an Ar atmosphere, the excited triplet state of the pentacene generated singlet oxygen by sensitization, and it reacted with the ground-state pentacene to give the 6,13-endoperoxide. The α-diketone deposited on glass was also converted successfully to pentacene film by photoirradiation. In addition, diketone precursors of a mixture of 2,8- and 2,9-dibromopentacene and 2,6-trianthrylene were also prepared and their photocon-version was performed.

Pentacene precursors for solution-processed OFETs

Uoyama, Hiroki,Yamada, Hiroko,Okujima, Tetsuo,Uno, Hidemitsu

, p. 6889 - 6894 (2010)

15-Acetoxy- and 15-hydroxy-6,13-dihydro-6,13-ethanopentacenes sublimed over 300 °C and no pentacene was formed below the temperature. The precursors bearing chlorinated epithiomethano bridges suffered complicated decomposition to give oligomeric pentacene derivatives. The precursor bearing an epithio-oxomethano bridge underwent smooth and clean conversion to pentacene by heat or light. An organic field-effect transistor fabricated by the spin-coating method of the precursor followed by light irradiation at 120 °C showed a good FET performance of μ=2.5×10-2 cm2 V -1 s-1 and on/off ratio=3.8×104.

Linear Acene Derivatives. New Routes to Pentacene and Naphthacene and the First Synthesis of a Triptycene with Two Anthracene Moieties

Luo, Jihmei,Hart, Harold

, p. 4833 - 4836 (1987)

The cycloaddition of o-xylylene to arene 1,4-endoxides was used to construct linear arene derivatives.For example, heating benzocyclobutene 4 with anthracene 1,4-endoxide (10) followed by dehydration and dehydrogenation gave pentacene in three steps and 64percent overall yield.An analogous sequence but with naphthalene 1,4-endoxides gave naphthacenes.Dehydration of the di adducts from 4 and anthracene 1,4:5,8-diendoxides (5) gave a mixture of 5,9,14,18- and 5,8,15,18-tetrahydroheptacenes 3 and 9.The previously unknown triptycene 2 was synthesized from 5,14-dihydropentacene (12), an intermediate in the new pentacene synthesis, in three steps and 29percent overall yield.

-

Bailey,Madoff

, p. 5603 (1953)

-

A Large Starphene Comprising Pentacene Branches

Holec, Jan,Cogliati, Beatrice,Lawrence, James,Berdonces-Layunta, Alejandro,Herrero, Pablo,Nagata, Yuuya,Banasiewicz, Marzena,Kozankiewicz, Boleslaw,Corso, Martina,de Oteyza, Dimas G.,Jancarik, Andrej,Gourdon, Andre

, p. 7752 - 7758 (2021)

Starphenes are attractive compounds due to their characteristic physicochemical properties that are inherited from acenes, making them interesting compounds for organic electronics and optics. However, the instability and low solubility of larger starphene homologs make their synthesis extremely challenging. Herein, we present a new strategy leading to pristine [16]starphene in preparative scale. Our approach is based on a synthesis of a carbonyl-protected starphene precursor that is thermally converted in a solid-state form to the neat [16]starphene, which is then characterised with a variety of analytical methods, such as 13C CP-MAS NMR, TGA, MS MALDI, UV/Vis and FTIR spectroscopy. Furthermore, high-resolution STM experiments unambiguously confirm its expected structure and reveal a moderate electronic delocalisation between the pentacene arms. Nucleus-independent chemical shifts NICS(1) are also calculated to survey its aromatic character.

Analysis of molecular aggregation states in pentacene thin films prepared from soluble precursor

Akinaga, Takahiro,Yasutake, Shigekazu,Sasaki, Sono,Sakata, Osami,Otsuka, Hideyuki,Takahara, Atsushi

, p. 1162 - 1163 (2006)

Molecular packing structure in pentacene films prepared from the Afzali's precursor soluble in general organic solvents was characterized by in-plane grazing-incidence X-ray diffraction (GIXD) measurements. The crystallographic ab plane of pentacene was parallel to the surface of a Si substrate. Crystal structure of pentacene near the substrate was identified as the thin-film phase. Copyright

Fast and inexpensive synthesis of pentacene with high yield using 6,13-pentacenequinone as precursor

Mota, María L.,Rodriguez, Bibiana,Carrillo, Amanda,Ambrosio, Roberto C.,Luque, Priscy A.,Mireles, Marcela,Vivaldo, Israel,Quevedo, Manuel A.

, p. 511 - 515 (2018)

Pentacene is an important semiconductor in the field of organic electronics. In this work is presented an alternative synthesis procedure to obtain pentacene from 6,13-pentacenequinone as a precursor. Synthesis of pentacene was performed in two reactions, Diels-Adler cycloaddition of 6,13-pentacenequinone followed by 6,13-pentacenequinone reduction to pentacene, employing LiAlH4 as reducing agent. The products were characterized by Fourier Transform Infrared Spectroscopy (FTIR), 1H-Nuclear Magnetic Resonance Spectroscopy (1H-NMR), X-Ray Diffraction (XRD), Thermogravimetric Analysis (TGA) and Ultraviolet–Visible Spectroscopy (UV-VIS). In this work, 6,13-pentacenequinone was synthetized with a high yield (55%) using an alternative method. The optimization process resulted in an overall reduction of reaction time while exhibiting high yield. The method presented here provides an affordable pentacene synthesis route with high purity, which can be further applied for research and development of organic electronic applications.

Photo precursor for pentacene

Uno, Hidemitsu,Yamashita, Yuko,Kikuchi, Makoto,Watanabe, Hikaru,Yamada, Hiroko,Okujima, Tetsuo,Ogawa, Takuji,Ono, Noboru

, p. 1981 - 1983 (2005)

6,13-Dihydro-6,13-ethanopentacene-15,16-dione gave pentacene efficiently both in solid and in solution by irradiation of light.

Thermal generation of pentacene from soluble precursors through expulsion of carbon dioxide

Huang, Hsin-Hui,Hsieh, Hsing-Hung,Wu, Chung-Chih,Lin, Chao-Chen,Chou, Pi-Tai,Chuang, Ta-Hsien,Wen, Yuh-Sheng,Chow, Tahsin J.

, p. 4494 - 4497 (2008)

Highly soluble pentacene precursors possessing ketal bridges across the rings were synthesized. Pure pentacene was produced through thermal dissociation, while carbon dioxide and ethylene were extruded as volatile fragments. Thin solid film of pentacene c

Alpha-diimine ligand compound, complex and preparation method of polyolefin lubricating oil base oil

-

Paragraph 0155-0158, (2020/07/24)

The present invention provides an alpha-diimine ligand compound having a structure represented by a formula (I), and further provides an alpha-diimine complex obtained from the ligand compound. In addition, the invention also provides a preparation method of polyolefin lubricating oil base oil taking the alpha-diimine complex as a catalyst and the prepared lubricant base oil. According to the ligand compound and the complex provided by the invention, a large steric hindrance group is introduced into a ligand skeleton, and the skeleton rigidity is increased, so that the chain walking capabilityof the complex as a catalyst is improved. The polyolefin lubricating oil base oil provided by the invention has high long-chain branch content and branching degree, can be used as medium-high viscosity lubricating oil base oil, simplifies the production process, reduces the production cost, is very suitable for industrial-scale production, and has excellent economic and social benefits.

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