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1714-29-0

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1714-29-0 Usage

Chemical Properties

White to yellow to light brown powder

Uses

Different sources of media describe the Uses of 1714-29-0 differently. You can refer to the following data:
1. 1-Bromopyrene is used in the cleavage of DNA in studies. It is also used in the preparation of DNA base analogs.
2. 1-Bromopyrene is suitable reagent used in the comparative study of effect of substituents of some pyrene derivatives in inducing phototoxicity, DNA damage and repair in human skin keratinocytes and light-induced lipid peroxidation in methanol. It is suitable reagent used in the study to investigate the UV photon-assisted thermal decomposition of PAHs at elevated temperature.1-Bromopyrene may be used as a standard to compare its spectral properties with that of pyrene based fluorescence probe. It may be used to study the effects of the addition of halogen hetero-atoms on the vapor pressures and thermodynamics of polycyclic aromatic hydrocarbons.It may be used in the synthesis of the following:2-methyl-4-pyren-1-yl-but-3-yn-2-ol1-ethynylpyrenesilsesquioxane (SSQ) based hybridruthenium nanoparticles functionalized with pyrene moietymono- and di-pyrenyl perfluoroalkanesoligo(1-bromopyrene)(OBrP) filmsdinitropyrene-derived DNA adduct

Preparation

1-Bromopyrene is an important intermediate in the OLED material industry. The synthesis method is as follows: pyrene is dissolved in an organic solvent dichloromethane, and dibromohydantoin is added for reaction, filtered, and the obtained solid is recrystallized to obtain 1-bromopyrene.

Synthesis Reference(s)

Synthetic Communications, 18, p. 2207, 1988 DOI: 10.1080/00397918808082362Synthesis of 1-Bromopyrene and 1-Pyrenecarbaldehyde

General Description

1-Bromopyrene, a polycyclic aromatic hydrocarbon (PAH), is a mono bromo substituted pyrene derivative. Its synthesis has been reported. Its gas phase UV-absorption spectra in the UV wavelength range at elevated temperature has been studied. Electron affinitiy (EA) of 1-bromopyrene has been investigated using electron attachment desorption chemical ionization mass spectrometry (DCI-MS) and triple quadrupole tandem mass spectrometry. It participates in the synthesis of novel ruthenium (II) bipyridine or terpyridine complexes bearing pyrene moiety. The reaction of 1-bromopyrene cation radical with water in acetonitrile has been analyzed using the electron transfer stopped-flow (ETSF) method.

Check Digit Verification of cas no

The CAS Registry Mumber 1714-29-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,7,1 and 4 respectively; the second part has 2 digits, 2 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 1714-29:
(6*1)+(5*7)+(4*1)+(3*4)+(2*2)+(1*9)=70
70 % 10 = 0
So 1714-29-0 is a valid CAS Registry Number.
InChI:InChI=1/C16H9Br/c17-14-9-12-5-1-3-10-7-8-11-4-2-6-13(14)16(11)15(10)12/h1-9H

1714-29-0 Well-known Company Product Price

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  • TCI America

  • (B1495)  1-Bromopyrene  >95.0%(GC)

  • 1714-29-0

  • 5g

  • 565.00CNY

  • Detail
  • TCI America

  • (B1495)  1-Bromopyrene  >95.0%(GC)

  • 1714-29-0

  • 25g

  • 1,980.00CNY

  • Detail
  • Alfa Aesar

  • (18280)  1-Bromopyrene, 95%   

  • 1714-29-0

  • 1g

  • 401.0CNY

  • Detail
  • Alfa Aesar

  • (18280)  1-Bromopyrene, 95%   

  • 1714-29-0

  • 5g

  • 1656.0CNY

  • Detail

1714-29-0SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-Bromopyrene

1.2 Other means of identification

Product number -
Other names 1-monobromopyrene

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:1714-29-0 SDS

1714-29-0Synthetic route

pyrene
129-00-0

pyrene

1-bromopyrene
1714-29-0

1-bromopyrene

Conditions
ConditionsYield
With N-Bromosuccinimide In dichloromethane for 2h;100%
With hydrogen bromide; dihydrogen peroxide In methanol; diethyl ether; water at 15 - 20℃; for 12.25h;96%
With N-Bromosuccinimide; dibenzoyl peroxide In N,N-dimethyl-formamide at 20℃;96%
C24H29BrO2

C24H29BrO2

1-bromopyrene
1714-29-0

1-bromopyrene

Conditions
ConditionsYield
With methanesulfonic acid In dichloromethane at 0 - 20℃; for 1h;96.08%
C24H29BrO2

C24H29BrO2

1-bromopyrene
1714-29-0

1-bromopyrene

Conditions
ConditionsYield
With methanesulfonic acid In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere;93.24%
C18H17BrO2

C18H17BrO2

1-bromopyrene
1714-29-0

1-bromopyrene

Conditions
ConditionsYield
With methanesulfonic acid In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere;91.1%
C18H17BrO2

C18H17BrO2

1-bromopyrene
1714-29-0

1-bromopyrene

Conditions
ConditionsYield
With methanesulfonic acid In dichloromethane at 0 - 20℃; for 1h;84.7%
tetrachloromethane
56-23-5

tetrachloromethane

N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

pyrene
129-00-0

pyrene

1-bromopyrene
1714-29-0

1-bromopyrene

N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

pyrene
129-00-0

pyrene

benzene
71-43-2

benzene

1-bromopyrene
1714-29-0

1-bromopyrene

Pyrene-1-carbonyl bromide

Pyrene-1-carbonyl bromide

1-bromopyrene
1714-29-0

1-bromopyrene

Conditions
ConditionsYield
With RhCl(PPh3)3 at 290℃;
pyridine
110-86-1

pyridine

pyrene
129-00-0

pyrene

bromine
7726-95-6

bromine

1-bromopyrene
1714-29-0

1-bromopyrene

tetrachloromethane
56-23-5

tetrachloromethane

pyrene
129-00-0

pyrene

bromine
7726-95-6

bromine

1-bromopyrene
1714-29-0

1-bromopyrene

pyrene
129-00-0

pyrene

chloroform
67-66-3

chloroform

bromine
7726-95-6

bromine

1-bromopyrene
1714-29-0

1-bromopyrene

pyrene
129-00-0

pyrene

water
7732-18-5

water

bromine
7726-95-6

bromine

1-bromopyrene
1714-29-0

1-bromopyrene

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

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

1-bromopyrene
1714-29-0

1-bromopyrene

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 / Inert atmosphere
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-bromo-2,2'-diformyl-1,1'-biphenyl

3-bromo-2,2'-diformyl-1,1'-biphenyl

1-bromopyrene
1714-29-0

1-bromopyrene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium t-butanolate / tetrahydrofuran / 0.5 h / 5 °C
1.2: 2 h / 5 - 30 °C
2.1: methanesulfonic acid / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
View Scheme
1-chloro-2,6-dinitrobenzene
606-21-3

1-chloro-2,6-dinitrobenzene

1-bromopyrene
1714-29-0

1-bromopyrene

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / ethanol; water; toluene / 8 h / 30 - 40 °C / Inert atmosphere
2.1: hydrogen; 5%-palladium/activated carbon / ethanol / 40 °C / 2250.23 Torr / Autoclave
3.1: copper(l) iodide; sodium nitrite; hydrogen iodide / water / 3 h / 5 - 60 °C
4.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -85 °C
4.2: 20 °C
5.1: sodium t-butanolate / tetrahydrofuran / 0.5 h / 5 °C
5.2: 2 h / 5 - 20 °C
6.1: methanesulfonic acid / dichloromethane / 1 h / 0 - 20 °C
View Scheme
(3-bromophenyl)boronic acid
89598-96-9

(3-bromophenyl)boronic acid

1-bromopyrene
1714-29-0

1-bromopyrene

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / ethanol; water; toluene / 8 h / 30 - 40 °C / Inert atmosphere
2.1: hydrogen; 5%-palladium/activated carbon / ethanol / 40 °C / 2250.23 Torr / Autoclave
3.1: copper(l) iodide; sodium nitrite; hydrogen iodide / water / 3 h / 5 - 60 °C
4.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -85 °C
4.2: 20 °C
5.1: sodium t-butanolate / tetrahydrofuran / 0.5 h / 5 °C
5.2: 2 h / 5 - 20 °C
6.1: methanesulfonic acid / dichloromethane / 1 h / 0 - 20 °C
View Scheme
3'-bromo-2,6-dinitro-1,1'-biphenyl

3'-bromo-2,6-dinitro-1,1'-biphenyl

1-bromopyrene
1714-29-0

1-bromopyrene

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: hydrogen; 5%-palladium/activated carbon / ethanol / 40 °C / 2250.23 Torr / Autoclave
2.1: copper(l) iodide; sodium nitrite; hydrogen iodide / water / 3 h / 5 - 60 °C
3.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -85 °C
3.2: 20 °C
4.1: sodium t-butanolate / tetrahydrofuran / 0.5 h / 5 °C
4.2: 2 h / 5 - 20 °C
5.1: methanesulfonic acid / dichloromethane / 1 h / 0 - 20 °C
View Scheme
3'-bromo-2,6-diamino-1,1'-biphenyl

3'-bromo-2,6-diamino-1,1'-biphenyl

1-bromopyrene
1714-29-0

1-bromopyrene

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: copper(l) iodide; sodium nitrite; hydrogen iodide / water / 3 h / 5 - 60 °C
2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -85 °C
2.2: 20 °C
3.1: sodium t-butanolate / tetrahydrofuran / 0.5 h / 5 °C
3.2: 2 h / 5 - 20 °C
4.1: methanesulfonic acid / dichloromethane / 1 h / 0 - 20 °C
View Scheme
3'-bromo-2,6-diiodo-1,1'-biphenyl

3'-bromo-2,6-diiodo-1,1'-biphenyl

1-bromopyrene
1714-29-0

1-bromopyrene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -85 °C
1.2: 20 °C
2.1: sodium t-butanolate / tetrahydrofuran / 0.5 h / 5 °C
2.2: 2 h / 5 - 20 °C
3.1: methanesulfonic acid / dichloromethane / 1 h / 0 - 20 °C
View Scheme
3'-bromo-2,6-diformyl-1,1'-biphenyl

3'-bromo-2,6-diformyl-1,1'-biphenyl

1-bromopyrene
1714-29-0

1-bromopyrene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium t-butanolate / tetrahydrofuran / 0.5 h / 5 °C
1.2: 2 h / 5 - 20 °C
2.1: methanesulfonic acid / dichloromethane / 1 h / 0 - 20 °C
View Scheme
3-bromobiphenyl
2113-57-7

3-bromobiphenyl

1-bromopyrene
1714-29-0

1-bromopyrene

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: nitric acid; sulfuric acid; acetic anhydride / dichloromethane / 4 h / 5 - 25 °C
2.1: hydrogen; 5%-palladium/activated carbon / ethanol / 40 °C / 2250.23 Torr / Autoclave
3.1: copper(l) iodide; sodium nitrite; hydrogen iodide / water / 3 h / 5 - 60 °C
4.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -85 °C / Inert atmosphere
4.2: 20 °C / Inert atmosphere
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-bromo-2,2'-dinitro-1,1'-biphenyl

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

1-bromopyrene
1714-29-0

1-bromopyrene

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: hydrogen; 5%-palladium/activated carbon / ethanol / 40 °C / 2250.23 Torr / Autoclave
2.1: copper(l) iodide; sodium nitrite; hydrogen iodide / water / 3 h / 5 - 60 °C
3.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -85 °C / Inert atmosphere
3.2: 20 °C / Inert atmosphere
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
3-bromo-2,2′-diaminebiphenyl

3-bromo-2,2′-diaminebiphenyl

1-bromopyrene
1714-29-0

1-bromopyrene

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: copper(l) iodide; sodium nitrite; hydrogen iodide / water / 3 h / 5 - 60 °C
2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -85 °C / Inert atmosphere
2.2: 20 °C / Inert atmosphere
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
1-bromopyrene
1714-29-0

1-bromopyrene

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

trimethyl(2-(pyren-1-yl)ethynyl)silane
253271-87-3

trimethyl(2-(pyren-1-yl)ethynyl)silane

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 70℃; for 20h;100%
With bis-triphenylphosphine-palladium(II) chloride; triethylamine at 70℃; for 23h; Sonogashira coupling; Inert atmosphere; Neat (no solvent); Sealed tube;99%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine at 20℃; for 24h; Inert atmosphere;99%
1-bromopyrene
1714-29-0

1-bromopyrene

1-pyrenylboronic acid
164461-18-1

1-pyrenylboronic acid

Conditions
ConditionsYield
With n-butyllithium; Triisopropyl borate100%
Stage #1: 1-bromopyrene With n-butyllithium In tetrahydrofuran at -78 - -10℃; for 0.833333h;
Stage #2: With Triisopropyl borate In tetrahydrofuran at 20℃; for 36h;
82%
Stage #1: 1-bromopyrene With n-butyllithium In diethyl ether at 0℃; for 0.5h;
Stage #2: With Trimethyl borate In diethyl ether at -78 - 20℃; for 26h;
Stage #3: In diethyl ether at 20℃; for 3h; Acid hydrolysis;
73%
1-bromopyrene
1714-29-0

1-bromopyrene

tributyl(thien-2-yl)stannane
54663-78-4

tributyl(thien-2-yl)stannane

2-(pyren-1-yl)thiophene
1040100-95-5

2-(pyren-1-yl)thiophene

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0) In toluene at 110℃; for 24h; Stille Cross Coupling; Inert atmosphere;100%
With tetrakis(triphenylphosphine) palladium(0) In toluene at 110℃; for 96h; Stille Cross-Coupling (Migita-Kosugi-Stille Coupling); Inert atmosphere;95%
With tetrakis(triphenylphosphine) palladium(0) In toluene for 24h; Inert atmosphere; Reflux;83.6%
With tetrakis(triphenylphosphine) palladium(0) In toluene Stille Cross Coupling; Inert atmosphere;
(4-(naphthalen-1-yl)phenyl)boronic acid
870774-25-7

(4-(naphthalen-1-yl)phenyl)boronic acid

1-bromopyrene
1714-29-0

1-bromopyrene

1-(4-naphthalene-1-yl-phenyl)pyrene

1-(4-naphthalene-1-yl-phenyl)pyrene

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water for 8h; Heating / reflux;99%
2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
61676-62-8

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

1-bromopyrene
1714-29-0

1-bromopyrene

1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrene
349666-24-6

1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrene

Conditions
ConditionsYield
Stage #1: 1-bromopyrene With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h;
Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran for 1h;
99%
Stage #1: 1-bromopyrene With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h;
Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran for 1h;
99%
Stage #1: 1-bromopyrene With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h;
Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran
99%
1-bromopyrene
1714-29-0

1-bromopyrene

tri(2-naphthyl)indium

tri(2-naphthyl)indium

1-(1-naphthalenyl)pyrene
88812-42-4

1-(1-naphthalenyl)pyrene

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); DavePhos In tetrahydrofuran at 80℃; Schlenk technique; Inert atmosphere;99%
2-methyl-3-buten-2-ol
115-18-4

2-methyl-3-buten-2-ol

1-bromopyrene
1714-29-0

1-bromopyrene

1-(3-hydroxy-3-methyl-1-butynyl)pyrene

1-(3-hydroxy-3-methyl-1-butynyl)pyrene

Conditions
ConditionsYield
With copper(l) iodide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; triphenylphosphine In toluene at 80℃; Inert atmosphere;99%
methanol
67-56-1

methanol

1-bromopyrene
1714-29-0

1-bromopyrene

1-methoxypyrene
34246-96-3

1-methoxypyrene

Conditions
ConditionsYield
With copper(l) iodide; sodium for 36h; Reflux; Inert atmosphere;98%
With copper(l) iodide In N,N-dimethyl-formamide for 3h; Heating;91%
With copper(l) iodide; sodium methylate In N,N-dimethyl-formamide for 30h; Heating;74%
1-bromopyrene
1714-29-0

1-bromopyrene

pyrene
129-00-0

pyrene

Conditions
ConditionsYield
With triethylamine In methanol; water at 4℃; for 0.25h; Irradiation; sensitizer: methylene blue;98%
With tetraethylammonium perchlorate; triethylamine In ethanol; dimethyl sulfoxide at 20℃; for 12h; Electrolysis; Green chemistry;92%
With tetrabutylammonium perchlorate In N,N-dimethyl-formamide at 22℃; Mechanism; electroreduction at Hg electrode, Pt counter electrode, current oscillations, other temperatures;
Multi-step reaction with 2 steps
1.1: n-butyllithium / tetrahydrofuran / 3 h / -78 °C
1.2: -78 - 20 °C
1.3: 1 h
2.1: caesium carbonate / 1-methyl-pyrrolidin-2-one; water / 10 h / 100 °C
View Scheme
1-bromopyrene
1714-29-0

1-bromopyrene

phenylacetylene
536-74-3

phenylacetylene

1-(phenylethynyl)pyrene
23975-18-0

1-(phenylethynyl)pyrene

Conditions
ConditionsYield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine for 48h; Reflux;98%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine at 80℃; for 48h; Inert atmosphere;69%
1-bromopyrene
1714-29-0

1-bromopyrene

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrene
349666-24-6

1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrene

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 90℃; for 4h; Inert atmosphere; Schlenk technique;98%
With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate In 1,4-dioxane at 80℃; Inert atmosphere;81%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 90℃; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique;80%
1-bromopyrene
1714-29-0

1-bromopyrene

2-methyl-but-3-yn-2-ol
115-19-5

2-methyl-but-3-yn-2-ol

1-(3-hydroxy-3-methyl-1-butynyl)pyrene

1-(3-hydroxy-3-methyl-1-butynyl)pyrene

Conditions
ConditionsYield
Stage #1: 1-bromopyrene With bis-triphenylphosphine-palladium(II) chloride; diethylamine at 50℃; Sonogashira Cross-Coupling;
Stage #2: 2-methyl-but-3-yn-2-ol With copper(l) iodide Reflux;
97%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine; triphenylphosphine In tetrahydrofuran Sonogashira Cross-Coupling; Reflux;76%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In various solvent(s)60%
With tetrakis(triphenylphosphine) palladium(0); triphenylphosphine; lithium bromide; copper(ll) bromide In tetrahydrofuran at 90℃; for 2h; Substitution; Title compound not separated from byproducts;
Stage #1: 1-bromopyrene; 2-methyl-but-3-yn-2-ol With piperidine; lithium bromide; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triphenylphosphine In tetrahydrofuran at 90℃; for 3h; Inert atmosphere;
Stage #2: With hydrogenchloride In tetrahydrofuran; dichloromethane; water
Thien-3-ylboronic acid
6165-69-1

Thien-3-ylboronic acid

1-bromopyrene
1714-29-0

1-bromopyrene

3-pyren-1-yl-thiophene

3-pyren-1-yl-thiophene

Conditions
ConditionsYield
With potassium carbonate In water; toluene at 90℃; for 0.5h; Suzuki-Miyaura Coupling;97%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In tetrahydrofuran; water Suzuki condensation;82%
morpholine
110-91-8

morpholine

1-bromopyrene
1714-29-0

1-bromopyrene

N-(1-pyrenyl)morpholine
1021359-33-0

N-(1-pyrenyl)morpholine

Conditions
ConditionsYield
With sodium t-butanolate; palladium diacetate In toluene at 80℃; for 1h; Buchwald-Hartwig amination;97%
1-bromopyrene
1714-29-0

1-bromopyrene

4-cyanophenylacetylene
3032-92-6

4-cyanophenylacetylene

4-(2-(pyren-1-yl)ethynyl)benzonitrile
54273-36-8

4-(2-(pyren-1-yl)ethynyl)benzonitrile

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); copper(II) sulfate; sodium L-ascorbate; triethylamine In N,N-dimethyl-formamide at 80℃; for 4h; Sonogashira coupling; Inert atmosphere;97%
Dichloromethyl methyl ether
4885-02-3

Dichloromethyl methyl ether

1-bromopyrene
1714-29-0

1-bromopyrene

6-bromo-pyrene-1-carbaldehyde

6-bromo-pyrene-1-carbaldehyde

Conditions
ConditionsYield
With titanium tetrachloride In dichloromethane at 20℃; for 3h; Cooling with ice;97%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

1-bromopyrene
1714-29-0

1-bromopyrene

2-mercaptoethylamine hydrochloride
156-57-0

2-mercaptoethylamine hydrochloride

C23H23NO2S
1492816-10-0

C23H23NO2S

Conditions
ConditionsYield
Stage #1: 1-bromopyrene; 2-mercaptoethylamine hydrochloride With potassium hydroxide In N,N-dimethyl-formamide at 20 - 110℃; for 1h; Inert atmosphere;
Stage #2: di-tert-butyl dicarbonate In N,N-dimethyl-formamide at 20℃; for 2h;
96%
ferroceneacetylene
1271-47-2

ferroceneacetylene

1-bromopyrene
1714-29-0

1-bromopyrene

(1-pyrenyl)ethynylferrocene
851537-08-1

(1-pyrenyl)ethynylferrocene

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine; triphenylphosphine at 88℃; for 8h; Sonogashira Cross-Coupling; Inert atmosphere; Schlenk technique;96%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In tetrahydrofuran at 70℃; for 24h; Sonogashira Cross-Coupling; Inert atmosphere;68%
2,5-Dimethylpyrrole
625-84-3

2,5-Dimethylpyrrole

1-bromopyrene
1714-29-0

1-bromopyrene

2-(pyrene-1-yl)-2,5-dimethyl-2H-pyrrole

2-(pyrene-1-yl)-2,5-dimethyl-2H-pyrrole

Conditions
ConditionsYield
Stage #1: 2,5-Dimethylpyrrole With n-butyllithium at 0℃; for 0.25h; Inert atmosphere;
Stage #2: 1-bromopyrene With bis(dibenzylideneacetone)-palladium(0); ruphos at 100℃; for 12h; Inert atmosphere; regioselective reaction;
96%
1-bromopyrene
1714-29-0

1-bromopyrene

phenylboronic acid
98-80-6

phenylboronic acid

1-phenyl pyrene
5101-27-9

1-phenyl pyrene

Conditions
ConditionsYield
Stage #1: 1-bromopyrene; phenylboronic acid With sodium methylate In ethanol Suzuki-Miyaura Coupling; Inert atmosphere;
Stage #2: In ethanol at 60℃; for 1h; Inert atmosphere;
96%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene at 90℃; for 24h; Inert atmosphere;70%
1-bromopyrene
1714-29-0

1-bromopyrene

sodium methylate
124-41-4

sodium methylate

1-methoxypyrene
34246-96-3

1-methoxypyrene

Conditions
ConditionsYield
In methanol for 15h; Inert atmosphere; Reflux; Large scale;95.2%
With copper(l) iodide In methanol for 36h; Inert atmosphere; Reflux;87.7%
With copper(l) iodide In N,N-dimethyl-formamide at 85℃; for 4h;84%
acrylaldehyde diethyl acetal
3054-95-3

acrylaldehyde diethyl acetal

1-bromopyrene
1714-29-0

1-bromopyrene

3-(pyrene-1-yl)propionic acid ethyl ester
83671-44-7

3-(pyrene-1-yl)propionic acid ethyl ester

Conditions
ConditionsYield
Stage #1: acrylaldehyde diethyl acetal; 1-bromopyrene With trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II); sodium acetate In 1-methyl-pyrrolidin-2-one at 140℃; for 6h;
Stage #2: With hydrogenchloride; water In 1-methyl-pyrrolidin-2-one
95%
4,4-difluoro-8-(p-(9-acetylenyl-1-ethynylpyrenyl)phenyl)-1,3,5,7-tetramethyl-2,4-diethyl-4-bora-3a,4a-diaza-s-indacene

4,4-difluoro-8-(p-(9-acetylenyl-1-ethynylpyrenyl)phenyl)-1,3,5,7-tetramethyl-2,4-diethyl-4-bora-3a,4a-diaza-s-indacene

1-bromopyrene
1714-29-0

1-bromopyrene

4,4-difluoro-8-(p-(9-(1-acetylenylpyrenyl)-1-ethynylpyrenyl)phenyl)-1,3,5,7-tetramethyl-2,4-diethyl-4-bora-3a,4a-diaza-s-indacene

4,4-difluoro-8-(p-(9-(1-acetylenylpyrenyl)-1-ethynylpyrenyl)phenyl)-1,3,5,7-tetramethyl-2,4-diethyl-4-bora-3a,4a-diaza-s-indacene

Conditions
ConditionsYield
With diisopropylamine; tetrakis(triphenylphosphine) palladium(0) In benzene at 20℃; for 16h; Sonogashira coupling;95%
1-bromopyrene
1714-29-0

1-bromopyrene

propargyl alcohol
107-19-7

propargyl alcohol

3-(pyren-1-yl)prop-2-yn-1-ol
1392406-87-9

3-(pyren-1-yl)prop-2-yn-1-ol

Conditions
ConditionsYield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); N-butylamine at 90℃; Inert atmosphere;95%
With tetrakis(triphenylphosphine) palladium(0); N-butylamine for 3h; Sonogashira Cross-Coupling; Reflux; Inert atmosphere;95%
1-bromopyrene
1714-29-0

1-bromopyrene

4-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)-9H-carbazole

4-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)-9H-carbazole

4-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)-9-(pyren-1-yl)-9H-carbazole

4-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)-9-(pyren-1-yl)-9H-carbazole

Conditions
ConditionsYield
With copper(l) iodide; 18-crown-6 ether; potassium carbonate In 1,2-dichloro-benzene at 190℃; for 24h; Reflux;95%
1-bromopyrene
1714-29-0

1-bromopyrene

N3,N3,N6,N6-tetrakis(4-methoxyphenyl)-9-H-carbazole-3,6-diamine

N3,N3,N6,N6-tetrakis(4-methoxyphenyl)-9-H-carbazole-3,6-diamine

N3,N3,N6,N6,tetrakis(4-methoxyphenyl)-9-(1-pyrene)-carbazole-3,6-diamine

N3,N3,N6,N6,tetrakis(4-methoxyphenyl)-9-(1-pyrene)-carbazole-3,6-diamine

Conditions
ConditionsYield
With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In toluene for 7h; Buchwald-Hartwig Coupling; Schlenk technique; Inert atmosphere; Reflux;95%
4-tert-Butylstyrene
1746-23-2

4-tert-Butylstyrene

1-bromopyrene
1714-29-0

1-bromopyrene

(E)-1-(4-tert-butylstyryl)pyrene
1338347-88-8

(E)-1-(4-tert-butylstyryl)pyrene

Conditions
ConditionsYield
With palladium diacetate; potassium carbonate; XPhos In N,N-dimethyl-formamide at 60℃; for 6h; Mizoroki-Heck reaction; Inert atmosphere; Pressure tube;94%
1-bromopyrene
1714-29-0

1-bromopyrene

4-Chlorophenylboronic acid
1679-18-1

4-Chlorophenylboronic acid

1-(4-chlorophenyl)pyrene
929099-49-0

1-(4-chlorophenyl)pyrene

Conditions
ConditionsYield
With sodium carbonate; palladium diacetate In 1,2-dimethoxyethane; water for 6.5h; Inert atmosphere; Reflux;94%

1714-29-0Relevant articles and documents

Effects of substituents on absorption and fluorescence properties of trimethylsilylethynyl- and tert-butylethynyl-pyrenes

Furuyama, Taniyuki,Maeda, Hajime,Segi, Masahito,Ueno, Ryota

, (2020)

Effects of substituents introduced at 1-position of trimethylsilylethynyl- and tert-butylethynyl-pyrenes on absorption and fluorescence properties were investigated. Fluorescence intensities of 1.0 × 10–5 M CH2Cl2 solutions of these pyrene derivatives were significantly larger than that of pyrene. Absorption of a silyl derivative having a formyl group shifted to longer wavelengths as the solvent polarity increased, whereas that of the carbon analog shifted to shorter wavelengths. On the other hand, in the solvent dependence of fluorescence, both fluorescence of them shifted to longer wavelengths as the polarity of the solvent increased. Fluorescence spectra of pyrene derivatives synthesized in this study at saturated concentrations in CH2Cl2 exhibited excimer emissions in the longer wavelength regions compared to that of unsubstituted pyrene. Fluorescence quantum yields of silicon analogs were higher than that of the corresponding carbon analogs in both solution and solid states. From the results of molecular orbital calculations, it was clarified that the effects of the substituents at the 1-position on the pyrene ring on the absorption and fluorescence properties can be explained by the properties of the molecular orbitals corresponding to the respective electron transitions.

Novel ethynyl-pyrene substituted phenothiazine based metal free organic dyes in DSSC with 12% conversion efficiency

Nagarajan, Bhanumathi,Kushwaha, Suman,Elumalai, Ramachandran,Mandal, Sudip,Ramanujam, Kothandaraman,Raghavachari, Dhamodharan

, p. 10289 - 10300 (2017)

Six new dyes based on phenothiazine conjugated to an ethynyl-pyrene moiety are synthesized and characterized. Dye-sensitized solar cells are fabricated using these dyes with and without a co-adsorbent, chenodeoxychloicacid. Simple molecular engineering around the phenothiazine moiety enabled a maximum of 12% photoconversion efficiency with one of the dyes.

3-pyrenylacrylates: Synthetic, photophysical, theoretical and electrochemical investigations

Reimann, Sebastian,Sharif, Muhammad,Wittler, Kai,Knoepke, Leif R.,Surkus, Annette-E.,Roth, Christian,Ludwig, Ralf,Langer, Peter

, p. 367 - 377 (2013)

The Mizoroki-Heck coupling of 1-bromopyrene with acrylates provides a convenient access to a variety of 3-pyrenylacrylates in very good yields (up to 93%). Their photophysical properties combined with solvatochromic effects were studied. In addition, electrochemical oxidation potentials were determined by DPV (differential pulse voltammetry) measurements. The fine structure of the absorbance spectra obtained from photophysical measurements are compared with the results of theoretical calculations performed by time dependent TD-B3LYP methods using the 6-31G* basis set.

Pyrene terminal functionalized perylene diimide as non-fullerene acceptors for bulk heterojunction solar cells

Liu, Xin,Luo, Guoping,Cai, Xinyi,Wu, Hongbin,Su, Shi-Jian,Cao, Yong

, p. 83155 - 83163 (2015)

Two perylene diimide (PDI) based small molecules with different terminal groups of pyrene and tert-butyl pyrene, namely P1 and P2, respectively, were designed and synthesized as the acceptor materials in organic solar cells (OSCs). The impacts of the different terminal groups combined with the PDI core on the optical absorption and fluorescence, electrochemical properties, film morphology, and solar cell performance were studied thoroughly. The two compounds possess a broad absorption covering the wavelength range of 400-650 nm and a relatively high LUMO energy level of 3.77 eV. Power conversion efficiency (PCE) of the OSCs based on P2 as the acceptor material and PTB7 as the donor material (1 : 1, w/w) is 0.41%. In contrast, a PCE of 1.35% was achieved for the device based on P1 as the acceptor and PTB7 as the donor (1 : 1, w/w).

The synthesis of polyarene-modified 5-phenyl-2,2'-bipyridines via the methodology and aza-Diels-Alder reaction

Kovalev, Igor S.,Kopchuk, Dmitry S.,Khasanov, Albert F.,Zyryanov, Grigory V.,Rusinov, Vladimir L.,Chupakhin, Oleg N.

, p. 117 - 118 (2014)

Nucleophilic substitution of hydrogen () in 6-phenyl-3-(2-pyridyl)-1,2,4- triazine under the action of lithium derivatives of polynuclear arenes followed by aza-Diels-Alder reaction with norbornadiene or morpholinocyclopentene gives the novel polyarenemodified photoluminescent 5-phenyl-2,2'-bipyridine ligands.

Synthesis and optoelectronic properties of novel organosoluble polynorbornenes containing asymmetric pyrenyl and electroactive substituents via ring-opening metathesis polymerization

Lian, Wei-Ren,Ho, Crystal,Huang, Ying-Chi,Liao, Yi-An,Wang, Kun-Li,Liaw, Der-Jang,Lee, Kueir-Rarn,Lai, Juin-Yih

, p. 5350 - 5357 (2011)

Novel polynorbornenes, poly(NBPYTPA), and poly(HNBPYTPA), containing chromophoric and electroactive groups were synthesized by ring-opening metathesis polymerization using Grubbs' catalysts and followed hydrogenation, respectively. The glass transition temperatures (Tg) of poly(NBPYTPA) and hydrogenated poly(HNBPYTPA) were 195 and 165 °C, respectively. The 10% weight-loss temperatures of hydrogenated poly(HNBPYTPA) and poly(NBPYTPA) were up to 465 and 420 °C, respectively. The photoluminescence emission spectra of poly(HNBPYTPA) showed strong solvatochromic property, revealing that poly(HNBPYTPA) underwent remarkable bathochromic shifts with an increase in solvent polarity. The cyclic voltammogram of poly(HNBPYTPA) film cast onto an indium tin oxide (ITO)-coated glass substrate exhibited two reversible oxidation redox couples at 0.8 and 1.2 V versus Ag/Ag+ in acetonitrile solution. The electrochromic characteristics of poly(HNBPYTPA) showed reversibility, with color changes from yellow to blue and then to red upon the application of potentials from 0 to 1.3 V.

Bis-selenonium Cations as Bidentate Chalcogen Bond Donors in Catalysis

He, Xinxin,Wang, Xinyan,Tse, Ying-Lung Steve,Ke, Zhihai,Yeung, Ying-Yeung

, p. 12632 - 12642 (2021/10/21)

Lewis acids are frequently employed in catalysis but they often suffer from high moisture sensitivity. In many reactions, catalysts are deactivated because of the problem that strong Lewis acids also bond to the products. In this research, hydrolytically stable bidentate Lewis acid catalysts derived from selenonium dicationic centers have been developed. The bis-selenonium catalysts are employed in the activation of imine and carbonyl groups in various transformations with good yields and selectivity. Lewis acidity of the bis-selenonium salts was found to be stronger than that of the monoselenonium systems, attributed to the synergistic effect of the two cationic selenonium centers. In addition, the bis-selenonium catalysts are not inhibited by strong bases or moisture.

Naphthoselenodiazole delayed-fluorescence material and preparation method thereof

-

Paragraph 0016-0018, (2021/07/28)

The invention belongs to the technical field of photoelectric display devices, and particularly relates to a naphthoselenodiazole delayed-fluorescence material and a preparation method thereof. The naphthoselenodiazole delayed-fluorescence material provided by the invention has a structural formula as shown in a formula (I) which is described in the specification. The invention also provides a preparation method of the naphthoselenodiazole delayed-fluorescence material. The preparation method comprises the following steps: carrying out a substitution reaction on a compound as shown in the formula (II) and a compound as shown in the formula (III) to prepare the compound as shown in the formula (I). The naphthoselenodiazole delayed-fluorescence material and the preparation method thereof provided by the invention solves the technical problems that existing red TADF materials are relatively difficult to synthesize and device efficiency is not high.

Pyridylquinoxaline delayed-luminescence derivative and preparation method thereof

-

Paragraph 0033-0035, (2021/07/28)

The invention relates to the technical field of photoelectric display devices, in particular to a pyridylquinoxaline delayed-luminescence derivative and a preparation method thereof. The pyridylquinoxaline delayed-luminescence derivative provided by the invention has a structure as shown in a formula (I) which is described in the specification. The invention also provides a preparation method of the pyridylquinoxaline delayed-luminescence derivative. The preparation method comprises the step that a compound as shown in a formula (II) and a compound as shown in a formula (V) are subjected to a substitution reaction to prepare the compound as shown in the formula (I). The pyridylquinoxaline delayed-luminescence derivative and the preparation method thereof provided by the invention solve the technical problems that existing red TADF materials are relatively difficult to synthesize and device efficiency is not high.

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