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27973-29-1

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27973-29-1 Usage

Description

1, 6-dibromopyrene is a kind of pyrene chemical. It is majorly used as organic intermediate, OLED (organic light-emitting diodes) materials and photoelectric material. It, together with its 1, 8- isomer, can be produced by the double bromination of pyrene with bromine. It can be applied to the synthesis of bipyridine and terpyridine based ruthenium metallosynthons.

Chemical Properties

white powder

References

Goze, Christine, et al. "Synthesis of bipyridine and terpyridine based ruthenium metallosynthons for grafting of multiple pyrene auxiliaries."Tetrahedron letters 44.48 (2003): 8713-8716. Kaplunov, Mikhail G., et al. "Novel 1, 8-bis(diarylamino)pyrenes as OLED materials." Mendeleev Communications 26.5(2016):437-439. Gong, Xiaojie, et al. "Two Symmetrically Bis‐substituted Pyrene Derivatives: Synthesis, Photoluminescence, and Electroluminescence." Chinese Journal of Chemistry 33.8 (2015): 967-973.

Check Digit Verification of cas no

The CAS Registry Mumber 27973-29-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,7,9,7 and 3 respectively; the second part has 2 digits, 2 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 27973-29:
(7*2)+(6*7)+(5*9)+(4*7)+(3*3)+(2*2)+(1*9)=151
151 % 10 = 1
So 27973-29-1 is a valid CAS Registry Number.
InChI:InChI=1/C16H8Br2/c17-13-8-4-10-2-6-12-14(18)7-3-9-1-5-11(13)16(10)15(9)12/h1-8H

27973-29-1 Well-known Company Product Price

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  • TCI America

  • (D3167)  1,6-Dibromopyrene  >98.0%(GC)

  • 27973-29-1

  • 1g

  • 890.00CNY

  • Detail
  • TCI America

  • (D3167)  1,6-Dibromopyrene  >98.0%(GC)

  • 27973-29-1

  • 5g

  • 2,450.00CNY

  • Detail

27973-29-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,6-Dibromopyrene

1.2 Other means of identification

Product number -
Other names 1,6-Dibrom-pyren

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:27973-29-1 SDS

27973-29-1Synthetic route

pyrene
129-00-0

pyrene

A

1,6-dibromopyrene
27973-29-1

1,6-dibromopyrene

B

1,8-dibromopyrene
38303-35-4

1,8-dibromopyrene

Conditions
ConditionsYield
With carbon disulfide; bromine at 20℃; for 17h;A 15%
B 85%
With carbon disulfide; bromine at 20℃; for 17h;A 15%
B 85%
With bromine In chloroform for 4h; Inert atmosphere; Reflux;A 71.1%
B 20%
C18H16Br2O2

C18H16Br2O2

1,6-dibromopyrene
27973-29-1

1,6-dibromopyrene

Conditions
ConditionsYield
With methanesulfonic acid In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere;82.2%
C24H28Br2O2

C24H28Br2O2

1,6-dibromopyrene
27973-29-1

1,6-dibromopyrene

Conditions
ConditionsYield
With methanesulfonic acid In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere;78.33%
pyrene
129-00-0

pyrene

1,6-dibromopyrene
27973-29-1

1,6-dibromopyrene

Conditions
ConditionsYield
With bromine In dichloromethane at 20℃; for 30h;64%
With bromine In tetrachloromethane at 110℃; for 12h; Darkness;63%
With bromine In chloroform at 23℃; for 8h;63%
1-hydropyrenyl

1-hydropyrenyl

1,6-dibromopyrene
27973-29-1

1,6-dibromopyrene

Conditions
ConditionsYield
With bromine In chloroform at 20℃;30%
1-bromopyrene
1714-29-0

1-bromopyrene

A

1,3-dibromopyrene
38037-54-6

1,3-dibromopyrene

B

1,6-dibromopyrene
27973-29-1

1,6-dibromopyrene

C

1,8-dibromopyrene
38303-35-4

1,8-dibromopyrene

Conditions
ConditionsYield
With bromine In dichloromethane for 5h; Ambient temperature;A 3 % Spectr.
B 53 % Spectr.
C 44 % Spectr.
1-amino-6-bromopyrene
42882-08-6

1-amino-6-bromopyrene

1,6-dibromopyrene
27973-29-1

1,6-dibromopyrene

Conditions
ConditionsYield
(i) NaNO2, aq. H2SO4, DMF, (ii) CuBr, KBr, aq. HBr; Multistep reaction;
pyrene
129-00-0

pyrene

dichloromethane
75-09-2

dichloromethane

bromine
7726-95-6

bromine

A

1,6-dibromopyrene
27973-29-1

1,6-dibromopyrene

B

1,8-dibromopyrene
38303-35-4

1,8-dibromopyrene

1-bromopyrene
1714-29-0

1-bromopyrene

A

1,6-dibromopyrene
27973-29-1

1,6-dibromopyrene

B

1,8-dibromopyrene
38303-35-4

1,8-dibromopyrene

C

1,3,6-tribromopyrene
38303-36-5

1,3,6-tribromopyrene

Conditions
ConditionsYield
With sodium hypochlorite; potassium bromide In methanol for 24h; pH=5;A n/a
B n/a
C 20 mg
1-bromo-6-nitropyrene
42882-03-1

1-bromo-6-nitropyrene

1,6-dibromopyrene
27973-29-1

1,6-dibromopyrene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N2H4*H2O / Raney-Ni
2: (i) NaNO2, aq. H2SO4, DMF, (ii) CuBr, KBr, aq. HBr
View Scheme
2Br(1-)*C16H8N4(2+)

2Br(1-)*C16H8N4(2+)

1,6-dibromopyrene
27973-29-1

1,6-dibromopyrene

Conditions
ConditionsYield
With hydrogen bromide; copper(I) bromide In water at 60℃; for 0.5h;
pyrene
129-00-0

pyrene

A

1,6-dibromopyrene
27973-29-1

1,6-dibromopyrene

B

1,4-dibromopyrene
857992-38-2

1,4-dibromopyrene

Conditions
ConditionsYield
With bromine In tetrachloromethane
pyrene
129-00-0

pyrene

A

1,6-dibromopyrene
27973-29-1

1,6-dibromopyrene

B

1,8-dibromopyrene
38303-35-4

1,8-dibromopyrene

C

1,3,6-tribromopyrene
38303-36-5

1,3,6-tribromopyrene

Conditions
ConditionsYield
With bromine In tetrachloromethane at 20℃; for 12h;
pyrene
129-00-0

pyrene

1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione
77-48-5

1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione

A

1,6-dibromopyrene
27973-29-1

1,6-dibromopyrene

B

1,8-dibromopyrene
38303-35-4

1,8-dibromopyrene

Conditions
ConditionsYield
In dichloromethane at 20℃; for 1h; Overall yield = 97 %; Overall yield = 398 mg;
3,3'-dibromo-2,2'-diamino-1,1'-biphenyl
10462-33-6

3,3'-dibromo-2,2'-diamino-1,1'-biphenyl

1,6-dibromopyrene
27973-29-1

1,6-dibromopyrene

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: hydrogen iodide; sulfuric acid / 0.17 h / 5 °C / Reflux
1.2: 3 h / 25 - 60 °C
2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -85 °C / Inert atmosphere
2.2: 20 °C
3.1: sodium t-butanolate / tetrahydrofuran / 0.5 h / 5 °C
3.2: 2 h / 5 - 30 °C
4.1: methanesulfonic acid / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
View Scheme
3,3'-dibromo-2,2'-diiodo-1,1'-biphenyl

3,3'-dibromo-2,2'-diiodo-1,1'-biphenyl

1,6-dibromopyrene
27973-29-1

1,6-dibromopyrene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -85 °C / Inert atmosphere
1.2: 20 °C
2.1: sodium t-butanolate / tetrahydrofuran / 0.5 h / 5 °C
2.2: 2 h / 5 - 30 °C
3.1: methanesulfonic acid / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
View Scheme
3,3'-dibromobiphenyl
16400-51-4

3,3'-dibromobiphenyl

1,6-dibromopyrene
27973-29-1

1,6-dibromopyrene

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: nitric acid; sulfuric acid / dichloromethane / 4 h / 5 - 25 °C
2.1: hydrogen; 5%-palladium/activated carbon / ethanol / 40 °C / 2250.23 Torr / Autoclave
3.1: hydrogen iodide; sulfuric acid / 0.17 h / 5 °C / Reflux
3.2: 3 h / 25 - 60 °C
4.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -85 °C / Inert atmosphere
4.2: 20 °C
5.1: sodium t-butanolate / tetrahydrofuran / 0.5 h / 5 °C
5.2: 2 h / 5 - 30 °C
6.1: methanesulfonic acid / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
View Scheme
3,3'-dibromo-2,2'-dinitro-1,1'-biphenyl

3,3'-dibromo-2,2'-dinitro-1,1'-biphenyl

1,6-dibromopyrene
27973-29-1

1,6-dibromopyrene

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: hydrogen; 5%-palladium/activated carbon / ethanol / 40 °C / 2250.23 Torr / Autoclave
2.1: hydrogen iodide; sulfuric acid / 0.17 h / 5 °C / Reflux
2.2: 3 h / 25 - 60 °C
3.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -85 °C / Inert atmosphere
3.2: 20 °C
4.1: sodium t-butanolate / tetrahydrofuran / 0.5 h / 5 °C
4.2: 2 h / 5 - 30 °C
5.1: methanesulfonic acid / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
View Scheme
1,6-dibromopyrene
27973-29-1

1,6-dibromopyrene

1,1-dimethylethyl 2-ethenyl-1H-pyrrole-1-carboxylate
180283-59-4

1,1-dimethylethyl 2-ethenyl-1H-pyrrole-1-carboxylate

1,6-bis((E)-2-(1H-pyrrol-2-yl)vinyl)pyrene

1,6-bis((E)-2-(1H-pyrrol-2-yl)vinyl)pyrene

Conditions
ConditionsYield
With palladium diacetate; potassium carbonate; acetylacetone In N,N-dimethyl-formamide at 130℃; for 6h; Heck Reaction; Inert atmosphere; Sealed tube;100%
1,6-dibromopyrene
27973-29-1

1,6-dibromopyrene

phenylboronic acid
98-80-6

phenylboronic acid

1,6-diphenylpyrene
55009-75-1

1,6-diphenylpyrene

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In water; toluene at 100℃; for 8h; Suzuki Coupling;99%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene for 24h; Suzuki Coupling; Inert atmosphere; Reflux;90%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water; toluene Reflux;87%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 5h; Inert atmosphere; Reflux;60%
1,6-dibromopyrene
27973-29-1

1,6-dibromopyrene

naphthalene-2-boronic acid
32316-92-0

naphthalene-2-boronic acid

1,6-bis(2-naphthyl)pyrene
663954-28-7

1,6-bis(2-naphthyl)pyrene

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; 1,2-dimethoxyethane; water at 90℃; for 8h;99%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; toluene for 24h; Suzuki coupling; Reflux; Inert atmosphere;71%
1,6-dibromopyrene
27973-29-1

1,6-dibromopyrene

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

1,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)pyrene
950779-13-2

1,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)pyrene

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In dimethyl sulfoxide at 80℃; for 16h; Miyaura Borylation Reaction; Schlenk technique; Inert atmosphere;99%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In dimethyl sulfoxide at 80℃; for 24h; Inert atmosphere;87.6%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In water; toluene for 12h; Reflux; Inert atmosphere;87%
1,6-dibromopyrene
27973-29-1

1,6-dibromopyrene

copper(l) cyanide

copper(l) cyanide

pyrene-1,6-dicarbonitrile
27973-30-4

pyrene-1,6-dicarbonitrile

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 150℃; for 24h;99%
In N,N-dimethyl-formamide at 170℃;93%
In N,N-dimethyl-formamide at 150℃; for 10h; Inert atmosphere;80%
1,6-dibromopyrene
27973-29-1

1,6-dibromopyrene

2-isopropenyl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane
126726-62-3

2-isopropenyl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

C22H18

C22H18

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene at 70 - 75℃; for 5.5h; Inert atmosphere;98.54%
1,6-dibromopyrene
27973-29-1

1,6-dibromopyrene

4-cyanophenylboronic acid
126747-14-6

4-cyanophenylboronic acid

1,6-di(4-cyanophenyl)pyrene

1,6-di(4-cyanophenyl)pyrene

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; 1,2-dimethoxyethane; water at 90℃; for 8h;98%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; N,N-dimethyl-formamide at 100℃; for 72h; Inert atmosphere;61.18%
4-isopropylphenyl-3,5-dimethylphenylamine
1208149-33-0

4-isopropylphenyl-3,5-dimethylphenylamine

1,6-dibromopyrene
27973-29-1

1,6-dibromopyrene

C50H48N2

C50H48N2

Conditions
ConditionsYield
With tri-tert-butyl phosphine; sodium t-butanolate; palladium diacetate In toluene at 100℃;98%
1,6-dibromopyrene
27973-29-1

1,6-dibromopyrene

4-(1-methylethyl)-N-[4-(1-methylethyl)phenyl]benzenamine
63451-41-2

4-(1-methylethyl)-N-[4-(1-methylethyl)phenyl]benzenamine

C52H52N2

C52H52N2

Conditions
ConditionsYield
With tri-tert-butyl phosphine; sodium t-butanolate; palladium diacetate In toluene at 100℃;97%
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene for 6h; Reflux; Inert atmosphere;62%
1,6-dibromopyrene
27973-29-1

1,6-dibromopyrene

2-Biphenylboronic acid
4688-76-0

2-Biphenylboronic acid

1,6-di(2-biphenyl)pyrene

1,6-di(2-biphenyl)pyrene

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water at 90℃; for 8h;97%
1,6-dibromopyrene
27973-29-1

1,6-dibromopyrene

4-(1-methylethyl)-N-[4-(1-methylethyl)phenyl]benzenamine
63451-41-2

4-(1-methylethyl)-N-[4-(1-methylethyl)phenyl]benzenamine

C52H52N2

C52H52N2

Conditions
ConditionsYield
With tri-tert-butyl phosphine; sodium t-butanolate; palladium diacetate In toluene at 100℃;97%
1,6-dibromopyrene
27973-29-1

1,6-dibromopyrene

2-(but-1-en-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

2-(but-1-en-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

C24H22

C24H22

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; toluene at 70 - 75℃; for 5.5h; Inert atmosphere;96.4%
1,6-dibromopyrene
27973-29-1

1,6-dibromopyrene

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

1,6-bis((trimethylsilyl)ethynyl)pyrene

1,6-bis((trimethylsilyl)ethynyl)pyrene

Conditions
ConditionsYield
Stage #1: 1,6-dibromopyrene With copper(l) iodide; triethylamine; triphenylphosphine for 0.5h; Inert atmosphere;
Stage #2: trimethylsilylacetylene With bis-triphenylphosphine-palladium(II) chloride for 18h; Reflux; Inert atmosphere;
94%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 80℃;93%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine In tetrahydrofuran; toluene at 120℃; for 1h; Microwave irradiation;88%
NH-pyrazole
288-13-1

NH-pyrazole

1,6-dibromopyrene
27973-29-1

1,6-dibromopyrene

C22H14N4

C22H14N4

Conditions
ConditionsYield
With copper(l) iodide; caesium carbonate In N,N-dimethyl-formamide at 120℃; for 40h; Schlenk technique; Inert atmosphere;94%
4-isopropyl-N-(para-tolyl)aniline
494834-22-9

4-isopropyl-N-(para-tolyl)aniline

1,6-dibromopyrene
27973-29-1

1,6-dibromopyrene

C48H44N2

C48H44N2

Conditions
ConditionsYield
With tri-tert-butyl phosphine; sodium t-butanolate; palladium diacetate In toluene at 100℃;93%
4-isopropyl-N-(para-tolyl)aniline
494834-22-9

4-isopropyl-N-(para-tolyl)aniline

1,6-dibromopyrene
27973-29-1

1,6-dibromopyrene

C48H44N2

C48H44N2

Conditions
ConditionsYield
With tri-tert-butyl phosphine; sodium t-butanolate; palladium diacetate at 100℃;93%
1,6-dibromopyrene
27973-29-1

1,6-dibromopyrene

N-(3-methylphenyl)-3-(9-phenyl-9H-fluoren-9-yl)phenylamine
1292285-22-3

N-(3-methylphenyl)-3-(9-phenyl-9H-fluoren-9-yl)phenylamine

N,N'-bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluoren-9-yl)phenyl]-pyrene-1,6-diamine
1292285-21-2

N,N'-bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluoren-9-yl)phenyl]-pyrene-1,6-diamine

Conditions
ConditionsYield
With tri-tert-butyl phosphine; sodium t-butanolate; bis(dibenzylideneacetone)-palladium(0) In hexane; toluene at 60 - 80℃; for 3h; Inert atmosphere;93%
With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In hexane; toluene at 60 - 80℃; for 3h; Inert atmosphere;93%
With tri-tert-butyl phosphine; sodium t-butanolate; bis(dibenzylideneacetone)-palladium(0) In hexane; toluene at 80℃; for 3h; Inert atmosphere;67%
benzophenone hydrazone
5350-57-2

benzophenone hydrazone

1,6-dibromopyrene
27973-29-1

1,6-dibromopyrene

C42H30N4

C42H30N4

Conditions
ConditionsYield
With palladium diacetate; sodium t-butanolate; XPhos In toluene at 90℃; for 3h;93%
1,6-dibromopyrene
27973-29-1

1,6-dibromopyrene

(4-(tert-butyl)-2-methoxyphenyl)boronic acid
1245928-51-1

(4-(tert-butyl)-2-methoxyphenyl)boronic acid

C38H38O2

C38H38O2

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium hydroxide In 1,4-dioxane; water at 100℃; Inert atmosphere;93%
1,6-dibromopyrene
27973-29-1

1,6-dibromopyrene

(4-(2-(3-methylphenyl)benzimidazol-1-yl)phenyl)boronic acid

(4-(2-(3-methylphenyl)benzimidazol-1-yl)phenyl)boronic acid

C56H38N4

C56H38N4

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 10h; Inert atmosphere; Reflux;93%
1,6-dibromopyrene
27973-29-1

1,6-dibromopyrene

bis-(3,4-dimethyl-phenyl)-amine
55389-75-8

bis-(3,4-dimethyl-phenyl)-amine

C48H44N2

C48H44N2

Conditions
ConditionsYield
With tri-tert-butyl phosphine; sodium t-butanolate; palladium diacetate In toluene at 100℃;92%
1,6-dibromopyrene
27973-29-1

1,6-dibromopyrene

bis-(3,4-dimethyl-phenyl)-amine
55389-75-8

bis-(3,4-dimethyl-phenyl)-amine

C48H44N2

C48H44N2

Conditions
ConditionsYield
With tri-tert-butyl phosphine; sodium t-butanolate; palladium diacetate In toluene at 100℃;92%
1,6-dibromopyrene
27973-29-1

1,6-dibromopyrene

4-phenyldiphenylamine
32228-99-2

4-phenyldiphenylamine

C52H36N2

C52H36N2

Conditions
ConditionsYield
With tri-tert-butyl phosphine; sodium t-butanolate; palladium diacetate In toluene at 100℃;92%
1,6-dibromopyrene
27973-29-1

1,6-dibromopyrene

4-methylphenylboronic acid
5720-05-8

4-methylphenylboronic acid

1,6-bis(4-methylphenyl)pyrene
908011-87-0

1,6-bis(4-methylphenyl)pyrene

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene for 24h; Suzuki Coupling; Inert atmosphere; Reflux;92%
1,6-dibromopyrene
27973-29-1

1,6-dibromopyrene

2-fluoro-4-(2-phenylbenzimidazolyl)benzeneboronic acid

2-fluoro-4-(2-phenylbenzimidazolyl)benzeneboronic acid

C54H32F2N4

C54H32F2N4

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 15h; Suzuki Coupling; Inert atmosphere; Reflux;91%
1,6-dibromopyrene
27973-29-1

1,6-dibromopyrene

C19H14BFN2O2

C19H14BFN2O2

C54H32F2N4

C54H32F2N4

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 15h; Inert atmosphere; Reflux;91%
1,6-dibromopyrene
27973-29-1

1,6-dibromopyrene

4-tert-butylphenylboronic acid
123324-71-0

4-tert-butylphenylboronic acid

1,6-bis(4-tert-butylphenyl)pyrene

1,6-bis(4-tert-butylphenyl)pyrene

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 85℃; for 16h; Inert atmosphere;91%
1,6-dibromopyrene
27973-29-1

1,6-dibromopyrene

octylmagnesium bromide
17049-49-9

octylmagnesium bromide

1,6-dioctylpyrene
1185354-41-9

1,6-dioctylpyrene

Conditions
ConditionsYield
Stage #1: octylmagnesium bromide With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); zinc(II) chloride In tetrahydrofuran for 0.5h; Inert atmosphere;
Stage #2: 1,6-dibromopyrene In tetrahydrofuran for 24h; Reflux;
91%
1,6-dibromopyrene
27973-29-1

1,6-dibromopyrene

2,2'-dinaphthylamine
532-18-3

2,2'-dinaphthylamine

C56H36N2

C56H36N2

Conditions
ConditionsYield
With tri-tert-butyl phosphine; sodium t-butanolate; palladium diacetate In toluene at 100℃;90%
1,6-dibromopyrene
27973-29-1

1,6-dibromopyrene

[4‐(5‐methyl‐2‐phenyl‐1H‐1,3‐benzodiazol‐1‐yl)phenyl]boronic acid

[4‐(5‐methyl‐2‐phenyl‐1H‐1,3‐benzodiazol‐1‐yl)phenyl]boronic acid

C56H38N4

C56H38N4

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 10h; Inert atmosphere; Reflux;90%

27973-29-1Relevant articles and documents

Synthesis and electro-optical properties of carbazole-substituted pyrene derivatives

Jeong, Seonju,Park, Sung Hwan,Kim, Ki-Soo,Kwon, Younghwan,Ha, Ki-Ryong,Choi, Byeong-Dae,Han, Yoon Soo

, p. 4351 - 4356 (2011)

Mono and dicarbazole-substituted pyrene derivatives, 9H-carbazol-9-ylpyrene (MCzP) and 1,6-di(9H-carbazol-9-yl)pyrene (DCzP), with dual-purpose function as a blue emitting and charge transporting layer in organic light emitting diodes, were synthesized and characterized. These series of molecules consisted of an electron donating (D) carbazole and an electron accepting (A) pyrene in D-A and D-A-D shapes. Non-doped blue electroluminescent devices with the configurations of ITO (150 nm)/α-NPD (30 nm)/DCzP (40 nm)/LiF (1 nm)/Al (150 nm) (D1) and ITO (150 nm)/2-TNATA (15 nm)/α-NPD (20 nm)/DCzP (40 nm)/BCP (15 nm)/Alq3(10 nm)/LiF (1 nm)/Al (120 nm) (D2) were fabricated. D1 and D2 devices showed blue emission at 492 nm and 488 nm, and maximum luminance of 840 and 7560 cd/m2 obtained at 13 V and 15 V, respectively. 2011 American Scientific Publishers Copyright

Electrophilic Substitution of Monosubstituted Pyrenes

Minabe, Masahiro,Takeshige, Shouji,Soeda, Yuuji,Kimura,Takao,Tsubota, Motohiro

, p. 172 - 179 (1994)

Bromination and Friedel-Crafts acetylation of monosubstituted pyrenes were examined.Acetylation of 1-acetyl- and 1-ethylpyrene occurred at the 8-, 6-, or 3-position, but the reaction of 1-methoxypyrene afforded only the 8- and 6-acetyl derivatives.By acetylation, 4-acetylpyrene yielded the 1- and 6-acetyl compounds, and 4-ethylpyrene gave the 6- and 8-derivatives.Also 4-bromopyrene afforded the corresponding 8-, 6-, and 1-acetyl derivatives by the same reaction.Bromination of 1-ethyl- and 4-ethylpyrene yielded the 8- and 6-bromides, but the reaction of 1-nitro- and 1-bromopyrene took place at the 6-, 8-, of 3-position.The formation ratio of these regioisomers differs by the substituents.The regioselectivity on the acetylation accords in some degree with the prediction based on the 13C NMR chemical shift of each position.The relative rates of these electrophilic substitutions correlate to the substituent constant, ?+, of the substituent attached to the pyrene.

A series of short axially symmetrically 1,3,6,8-tetrasubstituted pyrene-based green and blue emitters with 4-tert-butylphenyl and arylamine attachments

Zhang, Ran,Zhao, Yun,Zhang, Tengfei,Xu, Lu,Ni, Zhonghai

, p. 106 - 115 (2016)

A series of short axially symmetrically 1,3,6,8-tetrasubstituted pyrene-based derivatives (4a-4c) with two 4-tert-butylphenyl segments at 1,8-positions and two hole-transporting arylamine attachments at 3,6-sites of pyrene core were designed and synthesized based on stepwise synthetic strategy. These compounds were structurally characterized and their photoelectric properties were investigated by spectroscopy, electrochemical and theoretical studies. The results show that the incorporation of different arylamine units into pyrene core can tune the electronic structures of the compounds, and polysubstituted configuration of pyrene can effectively suppress the intermolecular π-π interactions and consequently leads to relatively high absolute fluorescence quantum efficiencies. These compounds exhibit high thermal stability and can form morphologically stable amorphous thin films with glass transition temperature in the range of 156-189 °C. Solution-processed non-doped green and blue organic light-emitting diodes with maximum luminance efficiencies 4.14 cd A-1 and 2.41 cd A-1 were achieved for 4b and 4c, respectively.

Novel phenylcarbazole type organic compounds and an organic electroluminescent device comprising the same

-

Paragraph 0157-0160, (2021/06/09)

An organic compound represented by chemical formula 1 and an organic light emitting device including the same are provided. Chemical Formula 1.

O-Doped Nanographenes: A Pyrano/Pyrylium Route Towards Semiconducting Cationic Mixed-Valence Complexes

Dor?evi?, Luka,Allain, Magali,Bonifazi, Davide,Coronado, Eugenio,Demitri, Nicola,Folli, Andrea,Mézière, Cécile,Ma?as-Valero, Samuel,Murphy, Damien,Sallé, Marc,Valentini, Cataldo

supporting information, p. 4106 - 4114 (2020/02/05)

Herein we report an efficient synthesis to prepare O-doped nanographenes derived from the π-extension of pyrene. The derivatives are highly fluorescent and feature low oxidation potentials. Using electrooxidation, crystals of cationic mixed-valence (MV) complexes were grown in which the organic salts organize into face-to-face π-stacks, a favorable solid-state arrangement for organic electronics. Variable-temperature electron paramagnetic resonance (EPR) measurements and relaxation studies suggest a strong electron delocalization along the longitudinal axis of the columnar π-stacking architectures. Electric measurements of single crystals of the MV salts show a semiconducting behavior with a remarkably high conductivity at room temperature. These findings support the notion that π-extension of heteroatom-doped polycyclic aromatic hydrocarbons is an attractive approach to fabricate nanographenes with a broad spectrum of semiconducting properties and high charge mobilities.

Templating Porphyrin Anisotropy via Magnetically Aligned Carbon Nanotubes

?or?evi?, Luka,Marangoni, Tomas,Liu, Mingjie,De Zorzi, Rita,Geremia, Silvano,Minoia, Andrea,Lazzaroni, Roberto,Ishida, Yasuhiro,Bonifazi, Davide

, p. 1270 - 1278 (2019/02/27)

The preparation and characterisation of a novel three-dimensional organic material consisting of porphyrin arrays on carbon nanotubes embedded in an organogel is reported. Firstly, the porphyrin array was prepared through metal-ligand coordination of a ditopic ligand (1,2-bis(4-pyridyl)ethane) and two bis-Zn(II) porphyrins, linked through a pyrene core, and was studied through UV-Vis, NMR and diffusion spectroscopies. Secondly, the porphyrin supramolecular architecture was adsorbed on pristine carbon nanotubes, greatly improving the dispersibility of the latter in organic solvents. The hybrid material was characterised by means of UV-Vis spectroscopy, microscopic techniques and thermogravimetric analysis. Finally, by exploiting the anisotropic magnetic susceptibility of carbon nanotubes, the hybrid material was aligned under a magnetic field, the organisation of which could be maintained by in situ gelation. The resultant hybrid organogel exhibited notable optical anisotropy, suggesting an anisotropic arrangement of the porphyrin-CNTs architectures in the macroscopic material.

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