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1044598-80-2

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  • Factory Price OLED 99% 1044598-80-2 2,5-bis(2-hexyldecyl)-3,6-di(thiophen-2-yl) pyrrolo[3,4-c]pyrrole- 1,4(2H,5H)-dione Manufacturer

    Cas No: 1044598-80-2

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1044598-80-2 Usage

General Description

2,5-Di(2-C6C10)-3,6-di(thiophen-2-yl)-diketopyrrolopyrrole is a complex chemical compound that is commonly used in the field of organic chemistry. It is a diketopyrrolopyrrole derivative, which means it contains a unique structure with two carbon rings and two thiophene rings. 2,5-Di(2-C6C10)-3,6-di(thiophen-2-yl)-diketopyrrolopyrrole has potential applications in the development of organic semiconductors, because of its unique properties, such as high electron mobility and good charge transport characteristics. It has also been studied for its potential use in organic photovoltaic devices, due to its strong absorption of light in the visible spectrum. Overall, 2,5-Di(2-C6C10)-3,6-di(thiophen-2-yl)-diketopyrrolopyrrole is a versatile compound with promising applications in the field of organic electronics and materials science.

Check Digit Verification of cas no

The CAS Registry Mumber 1044598-80-2 includes 10 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 7 digits, 1,0,4,4,5,9 and 8 respectively; the second part has 2 digits, 8 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 1044598-80:
(9*1)+(8*0)+(7*4)+(6*4)+(5*5)+(4*9)+(3*8)+(2*8)+(1*0)=162
162 % 10 = 2
So 1044598-80-2 is a valid CAS Registry Number.

1044598-80-2SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name 2,5-bis(2-hexyldecyl)-3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione

1.2 Other means of identification

Product number -
Other names 2,5-Di(2-C6C10)-3,6-di(thiophen-2-yl)-diketopyrrolopyrrole

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:1044598-80-2 SDS

1044598-80-2Synthetic route

3,6-dithiophen-2-yl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione

3,6-dithiophen-2-yl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione

7-(bromomethyl)pentadecane
52997-43-0

7-(bromomethyl)pentadecane

3,6-bis(5-bromothien-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
1044598-80-2

3,6-bis(5-bromothien-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione

Conditions
ConditionsYield
Stage #1: 3,6-dithiophen-2-yl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione With potassium carbonate In N,N-dimethyl-formamide at 145℃; for 2h; Inert atmosphere;
Stage #2: 7-(bromomethyl)pentadecane In N,N-dimethyl-formamide at 145℃; for 12h; Inert atmosphere;
46%
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 24h;36%
Stage #1: 3,6-dithiophen-2-yl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione With sodium hydride In N,N-dimethyl-formamide at 130℃; for 1h; Inert atmosphere;
Stage #2: 7-(bromomethyl)pentadecane In N,N-dimethyl-formamide at 130℃; Inert atmosphere;
13%
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 140℃; for 6h;
With 18-crown-6 ether; potassium carbonate In N,N-dimethyl-formamide at 120℃;
3,6-dithiophen-2-yl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione

3,6-dithiophen-2-yl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione

7-(bromomethyl)tridecane
115007-16-4

7-(bromomethyl)tridecane

A

3,6-bis(5-bromothien-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
1044598-80-2

3,6-bis(5-bromothien-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione

B

2-(2-hexyldecyl)-3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
1378896-41-3

2-(2-hexyldecyl)-3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione

Conditions
ConditionsYield
With 18-crown-6 ether; potassium carbonate In N,N-dimethyl-formamide at 120℃;A 33%
B 25%
3,6-dithiophen-2-yl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione

3,6-dithiophen-2-yl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione

7-(bromomethyl)pentadecane
52997-43-0

7-(bromomethyl)pentadecane

A

3,6-bis(5-bromothien-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
1044598-80-2

3,6-bis(5-bromothien-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione

B

7-methyleneheptadecane
13043-55-5, 17119-11-8

7-methyleneheptadecane

C

2-hexyldecanal
13893-35-1

2-hexyldecanal

Conditions
ConditionsYield
Stage #1: 3,6-dithiophen-2-yl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione With potassium carbonate In dimethyl sulfoxide at 140℃; for 0.75h; Inert atmosphere;
Stage #2: 7-(bromomethyl)pentadecane In dimethyl sulfoxide at 140℃; for 5h; Inert atmosphere;
A 25%
B n/a
C n/a
3,6-dithiophen-2-yl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione

3,6-dithiophen-2-yl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione

7-(iodomethyl)pentadecane
1044598-79-9

7-(iodomethyl)pentadecane

3,6-bis(5-bromothien-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
1044598-80-2

3,6-bis(5-bromothien-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 120℃;
thiophene-2-carbonitrile
1003-31-2

thiophene-2-carbonitrile

3,6-bis(5-bromothien-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
1044598-80-2

3,6-bis(5-bromothien-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium / tert-Amyl alcohol / 120 °C
2: potassium carbonate / N,N-dimethyl-formamide / 120 °C
View Scheme
Multi-step reaction with 2 steps
1: potassium tert-butylate / tert-Amyl alcohol / 4 h / 110 °C
2: potassium carbonate / N,N-dimethyl-formamide / 24 h / 110 °C
View Scheme
Multi-step reaction with 2 steps
1.1: potassium tert-butylate / tert-Amyl alcohol / 5 h / 110 °C / Inert atmosphere
2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 130 °C / Inert atmosphere
2.2: 130 °C / Inert atmosphere
View Scheme
3,6-bis(5-bromothien-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
1044598-80-2

3,6-bis(5-bromothien-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione

3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-di(2'-hexyldecyl)-pyrrolo[3,4c]pyrrolo-1,4-dione
1000623-98-2

3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-di(2'-hexyldecyl)-pyrrolo[3,4c]pyrrolo-1,4-dione

Conditions
ConditionsYield
With N-Bromosuccinimide In chloroform at 50℃; for 2h; Inert atmosphere;79.9%
With N-Bromosuccinimide In chloroform for 48h; Darkness;61%
With N-Bromosuccinimide In chloroform for 48h; Darkness;60%
3,6-bis(5-bromothien-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
1044598-80-2

3,6-bis(5-bromothien-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

2,5-bis(2-hexyldecyl)-3,6-bis(5-trimethylstannylthiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4-dione
1428651-72-2

2,5-bis(2-hexyldecyl)-3,6-bis(5-trimethylstannylthiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4-dione

Conditions
ConditionsYield
Stage #1: 3,6-bis(5-bromothien-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione With lithium diisopropyl amide In tetrahydrofuran at -78 - 20℃; for 2h; Inert atmosphere;
Stage #2: trimethyltin(IV)chloride In tetrahydrofuran at -78 - 20℃; Inert atmosphere;
71%
3,6-bis(5-bromothien-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
1044598-80-2

3,6-bis(5-bromothien-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione

3-(5-bromothiophen-2-yl)-2,5-bis(2-hexyldecyl)-6-(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
1423138-95-7

3-(5-bromothiophen-2-yl)-2,5-bis(2-hexyldecyl)-6-(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione

Conditions
ConditionsYield
With N-Bromosuccinimide In chloroform at 0 - 20℃; for 3.25h; Inert atmosphere;66%
With N-Bromosuccinimide In chloroform Inert atmosphere; Darkness;
With N-Bromosuccinimide; perchloric acid In chloroform; water at -10℃; for 2h;
3,6-bis(5-bromothien-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
1044598-80-2

3,6-bis(5-bromothien-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione

2-octyl-5-bromoisoindoline-1,3-dione
1255087-40-1

2-octyl-5-bromoisoindoline-1,3-dione

C78H110N4O6S2
1574407-35-4

C78H110N4O6S2

Conditions
ConditionsYield
With palladium diacetate; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 170℃; for 0.283333h; Microwave irradiation;63%
3,6-bis(5-bromothien-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
1044598-80-2

3,6-bis(5-bromothien-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

C48H72N2O4S2

C48H72N2O4S2

Conditions
ConditionsYield
Stage #1: 3,6-bis(5-bromothien-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 1h;
Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at -78 - 20℃; for 2h;
62%
3,6-bis(5-bromothien-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
1044598-80-2

3,6-bis(5-bromothien-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione

A

3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-di(2'-hexyldecyl)-pyrrolo[3,4c]pyrrolo-1,4-dione
1000623-98-2

3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-di(2'-hexyldecyl)-pyrrolo[3,4c]pyrrolo-1,4-dione

B

3-(5-bromothiophen-2-yl)-2,5-bis(2-hexyldecyl)-6-(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
1423138-95-7

3-(5-bromothiophen-2-yl)-2,5-bis(2-hexyldecyl)-6-(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione

Conditions
ConditionsYield
With N-Bromosuccinimide In chloroform at 0 - 20℃; Darkness;A 17%
B 56%
3,6-bis(5-bromothien-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
1044598-80-2

3,6-bis(5-bromothien-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione

3,5-dibromonitrobenzene
6311-60-0

3,5-dibromonitrobenzene

6,6'-((5-nitro-1,3-phenylene)bis(thiophene-5,2-diyl))bis(2,5-bis(2-hexyldecyl)-3-(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione)

6,6'-((5-nitro-1,3-phenylene)bis(thiophene-5,2-diyl))bis(2,5-bis(2-hexyldecyl)-3-(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione)

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); tris(o-methoxyphenyl)phosphine; caesium carbonate; Trimethylacetic acid In toluene at 100℃; for 24h; Schlenk technique; Inert atmosphere;50%
3,6-bis(5-bromothien-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
1044598-80-2

3,6-bis(5-bromothien-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione

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

C58H94B2N2O6S2

C58H94B2N2O6S2

Conditions
ConditionsYield
With lithium diisopropyl amide at -78 - 20℃;
3,6-bis(5-bromothien-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
1044598-80-2

3,6-bis(5-bromothien-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione

2-bromopyrene

2-bromopyrene

C78H90N2O2S2

C78H90N2O2S2

Conditions
ConditionsYield
With Trimethylacetic acid In toluene at 110℃; for 4h; Inert atmosphere;
3,6-bis(5-bromothien-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
1044598-80-2

3,6-bis(5-bromothien-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione

1,3-dibromo-5-fluorobenzene
1435-51-4

1,3-dibromo-5-fluorobenzene

6,6'-((5-fluoro-1,3-phenylene)bis(thiophene-5,2-diyl))bis(2,5-bis(2-hexyldecyl)-3-(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione)

6,6'-((5-fluoro-1,3-phenylene)bis(thiophene-5,2-diyl))bis(2,5-bis(2-hexyldecyl)-3-(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione)

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); tris(o-methoxyphenyl)phosphine; caesium carbonate; Trimethylacetic acid In toluene at 100℃; for 24h; Schlenk technique; Inert atmosphere;103.0 mg
3,6-bis(5-bromothien-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
1044598-80-2

3,6-bis(5-bromothien-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione

1,3-dibromo-5-chlorobenzene
14862-52-3

1,3-dibromo-5-chlorobenzene

6,6'-((5-chloro-1,3-phenylene)bis(thiophene-5,2-diyl))bis(2,5-bis(2-hexyldecyl)-3-(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione)

6,6'-((5-chloro-1,3-phenylene)bis(thiophene-5,2-diyl))bis(2,5-bis(2-hexyldecyl)-3-(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione)

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); tris(o-methoxyphenyl)phosphine; caesium carbonate; Trimethylacetic acid In toluene at 100℃; for 24h; Schlenk technique; Inert atmosphere;97.69 mg
3,6-bis(5-bromothien-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
1044598-80-2

3,6-bis(5-bromothien-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione

3,5-dibromoanisole
74137-36-3

3,5-dibromoanisole

6,6'-((5-methoxy-1,3-phenylene)bis(thiophene-5,2-diyl))bis(2,5-bis(2-hexyldecyl)-3-(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione)

6,6'-((5-methoxy-1,3-phenylene)bis(thiophene-5,2-diyl))bis(2,5-bis(2-hexyldecyl)-3-(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione)

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); tris(o-methoxyphenyl)phosphine; caesium carbonate; Trimethylacetic acid In toluene at 100℃; for 24h; Schlenk technique; Inert atmosphere;90.80 mg
3,6-bis(5-bromothien-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
1044598-80-2

3,6-bis(5-bromothien-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione

3,5-dibromo-1,1′-biphenyl
16372-96-6

3,5-dibromo-1,1′-biphenyl

6,6'-(([1,1'-biphenyl]-3,5-diyl)bis(thiophene-5,2-diyl))bis(2,5-bis(2-hexyldecyl)-3-(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione)

6,6'-(([1,1'-biphenyl]-3,5-diyl)bis(thiophene-5,2-diyl))bis(2,5-bis(2-hexyldecyl)-3-(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione)

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); tris(o-methoxyphenyl)phosphine; caesium carbonate; Trimethylacetic acid In toluene at 100℃; for 24h; Schlenk technique; Inert atmosphere;126.09 mg
1,4-dibromo-2,3-difluoro-benzene
156682-52-9

1,4-dibromo-2,3-difluoro-benzene

3,6-bis(5-bromothien-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
1044598-80-2

3,6-bis(5-bromothien-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione

6,6'-((2,3-difluoro-1,4-phenylene)bis(thiophene-5,2-diyl))bis(2,5-bis(2-hexyldecyl)-3-(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione)

6,6'-((2,3-difluoro-1,4-phenylene)bis(thiophene-5,2-diyl))bis(2,5-bis(2-hexyldecyl)-3-(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione)

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); tris(o-methoxyphenyl)phosphine; caesium carbonate; Trimethylacetic acid In toluene at 100℃; for 24h; Schlenk technique; Inert atmosphere;92.15 mg
3,6-bis(5-bromothien-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
1044598-80-2

3,6-bis(5-bromothien-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione

1,4-dibromo-2,5-difluorobenzene
327-51-5

1,4-dibromo-2,5-difluorobenzene

6,6'-(5,5'-(2,5-difluoro-1,4-phenylene)bis(thiophene-5,2-diyl))bis(2,5-bis(2-hexyldecyl)-3-(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione)

6,6'-(5,5'-(2,5-difluoro-1,4-phenylene)bis(thiophene-5,2-diyl))bis(2,5-bis(2-hexyldecyl)-3-(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione)

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); tris(o-methoxyphenyl)phosphine; caesium carbonate; Trimethylacetic acid In toluene at 100℃; for 24h; Schlenk technique; Inert atmosphere;80.36 mg
3,6-bis(5-bromothien-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
1044598-80-2

3,6-bis(5-bromothien-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione

1,4-dibromo-2,5-dichlorobenzene
4571-24-8

1,4-dibromo-2,5-dichlorobenzene

6,6'-((2,5-dichloro-1,4-phenylene)bis(thiophene-5,2-diyl))bis(2,5-bis(2-hexyldecyl)-3-(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione)

6,6'-((2,5-dichloro-1,4-phenylene)bis(thiophene-5,2-diyl))bis(2,5-bis(2-hexyldecyl)-3-(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione)

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); tris(o-methoxyphenyl)phosphine; caesium carbonate; Trimethylacetic acid In toluene at 100℃; for 24h; Schlenk technique; Inert atmosphere;104.87 mg
3,6-bis(5-bromothien-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
1044598-80-2

3,6-bis(5-bromothien-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione

1,4-dibromo-2,5-dimethoxybenzene
2674-34-2

1,4-dibromo-2,5-dimethoxybenzene

6,6'-((2,5-dimethoxy-1,4-phenylene)bis(thiophene-5,2-diyl))bis(2,5-bis(2-hexyldecyl)-3-(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione)

6,6'-((2,5-dimethoxy-1,4-phenylene)bis(thiophene-5,2-diyl))bis(2,5-bis(2-hexyldecyl)-3-(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione)

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); tris(o-methoxyphenyl)phosphine; caesium carbonate; Trimethylacetic acid In toluene at 100℃; for 24h; Schlenk technique; Inert atmosphere;80.80 mg

1044598-80-2Relevant articles and documents

Diketopyrrolopyrrole-based acceptor-acceptor conjugated polymers: The importance of comonomer on their charge transportation nature

Ge, Cong-Wu,Mei, Chong-Yu,Ling, Jun,Zhao, Fu-Gang,Li, Hong-Jiao,Liang, Long,Wang, Jin-Tu,Yu, Jin-Cheng,Shao, Wei,Xie, Yong-Shu,Li, Wei-Shi

, p. 2356 - 2366 (2014)

Besides the donor-acceptor (D-A) type, acceptor-acceptor (A-A) polymers are another class of important alternative conjugated copolymers, but have been less studied in the past. In this study, two kinds of A-A polymers, P1 and P2, have been designed and synthesized based on diketopyrrolopyrrole in combination with the second electron-deficient unit, perylenediimide or thieno[3,4-c] pyrrole-4,6-dione. UV-vis absorption spectroscopy revealed that these two kinds of polymers have a band gap of 1.28-1.33 eV. Their highest occupied molecular orbital and lowest unoccupied molecular orbital energy levels are around -5.6 and -4.0 eV for P1 polymers, whereas -5.4 and -3.7 eV for P2 polymers, respectively. Density functional theory study disclosed that P1 backbone is in a vastly twisting state, whereas that of P2 is completely planar. Furthermore, organic field-effect transistor devices were fabricated using these two kinds of polymers as the active material. Of interest, the devices based on P1 polymers displayed n-channel behaviors with an electron mobility in the order of 10 -4 cm2 V-1 s-1. In contrast, the P2-based devices exhibited only p-channel charge transportation characteristics with a hole mobility in the order of 10-3 cm2 V -1 s-1.

Rapid release from near-infrared polymer loaded liposomes for photothermal and chemo-combined therapy

Li, Dehua,Zhang, Meiduo,Yao, Jingke,Zhang, Zhe

supporting information, p. 2274 - 2277 (2019/02/05)

PEGylated liposomal doxorubicin is a polymeric antitumor drug approved clinically by the Food and Drug Administration, but it has no essentially increasing efficacy compared to free doxorubicin (DOX) because of the slow release rate. In this paper, a near-infrared polymer was designed and encapsulated in liposomes to photothermally accelerate the release of DOX. This polymer loaded liposome provides a maximum absorption that covers the ideal phototherapeutic window between 800 and 850 nm, which ensures an efficient photothermal release of DOX as a nano drug for the delivery of photothermal and chemo-combined therapy in a highly efficient cancer treatment.

Importance of solubilizing group and backbone planarity in low band gap polymers for high performance ambipolar field-effect transistors

Lee, Joong Suk,Son, Seon Kyoung,Song, Sanghoon,Kim, Hyunjung,Lee, Dong Ryoul,Kim, Kyungkon,Ko, Min Jae,Choi, Dong Hoon,Kim, Bong Soo,Cho, Jeong Ho

, p. 1316 - 1323 (2012/08/28)

We investigated the performance of ambipolar field-effect transistors based on a series of alternating low band gap polymers of oligothiophene and diketopyrrolopyrrole (DPP). The polymers contain oligothiophene units of terthiophene [T3] and thiophenethienothiophene-thiophene [T2TT] and DPP units carrying branched alkyl chains of 2-hexyldecyl [HD] or 2-octyldodecyl [OD]. The structural variation allows us to do a systematic study on the relationship between the interchain stacking/ordering of semiconducting polymers and their resulting device performance. On the basis of synchrotron X-ray diffraction and atomic force microscopy measurements on polymer films, we found that longer branched alkyl side chains, i.e., OD, and longer and more planar oligothiophene, i.e., T2TT, generate the more crystalline structures. Upon thermal annealing, the crystallinity of the polymers was largely improved, and polymers containing a longer branched alkyl chain responded faster because longer alkyl chains have larger cohesive forces than shorter chains. For all the polymers, excellent ambipolar behavior was observed with a maximum hole and electron mobility of 2.2 and 0.2 cm2 V-1 ss, respectively.

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