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201611-92-9

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201611-92-9 Usage

Description

4-CYANO-4-(THIOBENZOYLTHIO)PENTANOIC ACID, also known as a RAFT agent, is a sulfur-based compound utilized in controlled radical polymerizations. It is particularly effective in the Reversible Addition Fragmentation Chain Transfer (RAFT) polymerization technique, providing a high degree of control over the process. This molecule is characterized by its ability to facilitate the formation of polymers with specific properties, making it a valuable tool in the field of polymer chemistry.

Uses

Used in Polymer Synthesis:
4-CYANO-4-(THIOBENZOYLTHIO)PENTANOIC ACID is used as a Chain Transfer Agent (CTA) for controlled radical polymerization, allowing for the production of polymers with well-defined structures and properties. This is particularly important in the development of materials with specific applications in various industries.
Used in RAFT Polymerization:
In the field of RAFT Polymerization, 4-CYANO-4-(THIOBENZOYLTHIO)PENTANOIC ACID is used as a RAFT agent to control the polymerization process. Its use enables the synthesis of polymers with a narrow molecular weight distribution and predictable molecular weights, which is crucial for the development of high-performance materials.
Used in the Polymerization of Methacrylate and Methacrylamide Monomers:
4-CYANO-4-(THIOBENZOYLTHIO)PENTANOIC ACID is especially suited for the polymerization of methacrylate and methacrylamide monomers. As a RAFT agent, it allows for the controlled synthesis of these monomers, which are widely used in the production of various materials, including coatings, adhesives, and biomedical applications.
Used in the Development of High-Performance Materials:
4-CYANO-4-(THIOBENZOYLTHIO)PENTANOIC ACID plays a vital role in the development of high-performance materials by enabling the synthesis of polymers with tailored properties. These materials can be used in a range of applications, from advanced coatings and adhesives to biomedical devices and drug delivery systems.

Check Digit Verification of cas no

The CAS Registry Mumber 201611-92-9 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 2,0,1,6,1 and 1 respectively; the second part has 2 digits, 9 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 201611-92:
(8*2)+(7*0)+(6*1)+(5*6)+(4*1)+(3*1)+(2*9)+(1*2)=79
79 % 10 = 9
So 201611-92-9 is a valid CAS Registry Number.
InChI:InChI=1/C13H13NO2S2/c1-13(9-14,8-7-11(15)16)18-12(17)10-5-3-2-4-6-10/h2-6H,7-8H2,1H3,(H,15,16)

201611-92-9SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-(benzenecarbonothioylsulfanyl)-4-cyanopentanoic acid

1.2 Other means of identification

Product number -
Other names 4-Cyano-4-(thiobenzoylthio)pentanoic acid

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:201611-92-9 SDS

201611-92-9Synthetic route

bis(thiobenzoyl) disulfide
5873-93-8

bis(thiobenzoyl) disulfide

4,4'-dicyano-4,4'-azo-di-valeric acid
2638-94-0

4,4'-dicyano-4,4'-azo-di-valeric acid

4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

Conditions
ConditionsYield
In ethyl acetate at 85℃; for 12h; Inert atmosphere;75%
In ethyl acetate for 18h; Heating;68%
In ethyl acetate Reflux;65%
4,4'-dicyano-4,4'-azo-di-valeric acid
2638-94-0

4,4'-dicyano-4,4'-azo-di-valeric acid

4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

Conditions
ConditionsYield
With pyrrol-N-thiocarbonyl disulfides In ethyl acetate for 20h;59%
Multi-step reaction with 3 steps
1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 3 h / 20 °C
2: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Inert atmosphere
3: ethyl acetate / 20 h / 80 °C / Inert atmosphere
View Scheme
polymer, obtained by reversible addition fragmentation chain-transfer; monomer(s): 4-cyanopentanoic acid dithiobenzoate

polymer, obtained by reversible addition fragmentation chain-transfer; monomer(s): 4-cyanopentanoic acid dithiobenzoate

4,4'-dicyano-4,4'-azo-di-valeric acid
2638-94-0

4,4'-dicyano-4,4'-azo-di-valeric acid

A

polymer, Mn (SEC) = 23500, PDI (SEC) = 1.05; monomer(s): 4-cyanopentanoic acid dithiobenzoate; 4,4'-azobis(4-cyanopentanoic acid)

polymer, Mn (SEC) = 23500, PDI (SEC) = 1.05; monomer(s): 4-cyanopentanoic acid dithiobenzoate; 4,4'-azobis(4-cyanopentanoic acid)

B

4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

Conditions
ConditionsYield
In methanol at 80℃; for 3h;A 82%
B n/a
dithiobenzoic acid
121-68-6

dithiobenzoic acid

4,4'-dicyano-4,4'-azo-di-valeric acid
2638-94-0

4,4'-dicyano-4,4'-azo-di-valeric acid

4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

Conditions
ConditionsYield
Stage #1: dithiobenzoic acid With iodine; dimethyl sulfoxide In ethyl acetate for 10h;
Stage #2: 4,4'-dicyano-4,4'-azo-di-valeric acid In ethyl acetate for 18h; Heating;
44%
benzyl chloride
100-44-7

benzyl chloride

4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium methylate; sulfur / methanol / 10 h / Inert atmosphere; Reflux
2.1: sodium hydroxide / water
2.2: 1 h
3.1: ethyl acetate / 18 h / Reflux
View Scheme
Multi-step reaction with 3 steps
1: sodium; sulfur / methanol / 10.25 h / 65 °C
2: iodine / dimethyl sulfoxide; ethyl acetate / 20 °C / Darkness
3: ethyl acetate / 16 h / 77 °C
View Scheme
Multi-step reaction with 3 steps
1: sulfur; sodium methylate / methanol / 10 h / Reflux; Inert atmosphere
2: potassium hexacyanoferrate (III) / 1 h
3: ethyl acetate / 18 h / Reflux
View Scheme
dithiobenzoic acid sodium salt
3682-36-8

dithiobenzoic acid sodium salt

4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium ferricyanide / H2O / 1 h / 20 °C
2: ethyl acetate / 28.5 h / 70 °C
View Scheme
Multi-step reaction with 2 steps
1: potassium hexacyanoferrate (III) / 1 h
2: ethyl acetate / 18 h / Reflux
View Scheme
benzyl chloride
100-44-7

benzyl chloride

N,N-diethyl-glycine-<4-hydroxy-anilide>

N,N-diethyl-glycine-<4-hydroxy-anilide>

4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sulfur; MeONa / methanol / 10 h / 70 °C
2: potassium ferricyanide / H2O / 1 h / 20 °C
3: ethyl acetate / 28.5 h / 70 °C
View Scheme
dithiobenzoic acid
121-68-6

dithiobenzoic acid

4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: iodine; dimethyl sulfoxide / ethanol / 2 h / 20 °C
2: ethyl acetate / 20 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1.1: sodium hydroxide / water
1.2: 1 h
2.1: ethyl acetate / 18 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1: iodine / dimethyl sulfoxide; ethyl acetate / 20 °C / Darkness
2: ethyl acetate / 16 h / 77 °C
View Scheme
bis(thiobenzoyl) disulfide
5873-93-8

bis(thiobenzoyl) disulfide

C48H54N10O6
1268268-75-2

C48H54N10O6

4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

Conditions
ConditionsYield
In ethyl acetate at 80℃; for 20h; Inert atmosphere;34%
bis(dithiobenzoyl) disulfide

bis(dithiobenzoyl) disulfide

4,4'-dicyano-4,4'-azo-di-valeric acid
2638-94-0

4,4'-dicyano-4,4'-azo-di-valeric acid

4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

Conditions
ConditionsYield
In ethyl acetate at 20℃; for 28h; Reflux;
bromobenzene
108-86-1

bromobenzene

4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: iodine; magnesium / tetrahydrofuran / 1 h
1.2: 2 h / 0 °C
2.1: iodine; dimethyl sulfoxide / ethanol / 2 h / 20 °C
3.1: ethyl acetate / 20 h / 80 °C / Inert atmosphere
View Scheme
chloride of 4,4'-azo-bis(4-cyanopentanoic) acid chloride
17170-81-9

chloride of 4,4'-azo-bis(4-cyanopentanoic) acid chloride

4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Inert atmosphere
2: ethyl acetate / 20 h / 80 °C / Inert atmosphere
View Scheme
N,N-Dimethylacrylamide
2680-03-7

N,N-Dimethylacrylamide

4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

poly(N,N-dimethylacrylamide), Mn 8200, Mw/Mn 1.08, product of RAFT polymerization with 4-carboxy-2-cyanobutyl-2-yl dithiobenzoate; monomer(s): N,N-dimethylacrylamide; 4-carboxy-2-cyanobutyl-2-yl dithiobenzoate

poly(N,N-dimethylacrylamide), Mn 8200, Mw/Mn 1.08, product of RAFT polymerization with 4-carboxy-2-cyanobutyl-2-yl dithiobenzoate; monomer(s): N,N-dimethylacrylamide; 4-carboxy-2-cyanobutyl-2-yl dithiobenzoate

Conditions
ConditionsYield
With hydrogenchloride; 4,4'-dicyano-4,4'-azo-di-valeric acid In acetate buffer at 80℃; for 0.333333h; pH=5;96.73%
4-pyrenylbutanol
67000-89-9

4-pyrenylbutanol

4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

4-cyano-4-methyl-4-thiobenzoylsulfanyl-butyric acid 4-pyren-1-yl-butyl ester
1048735-14-3

4-cyano-4-methyl-4-thiobenzoylsulfanyl-butyric acid 4-pyren-1-yl-butyl ester

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran; dichloromethane at 0 - 20℃;95%
4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

3-bromopropyl 4-((benzenethiocarbonyl)thio)-4-cyanopentanoate
1414117-60-4

3-bromopropyl 4-((benzenethiocarbonyl)thio)-4-cyanopentanoate

Conditions
ConditionsYield
With dmap In dichloromethane at 20℃; for 18h; Inert atmosphere;93.9%
poly(methacrylic acid)
79-41-4

poly(methacrylic acid)

triethylamine
121-44-8

triethylamine

4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

polymer, molecular weight distribution = 1.12, Mn = 8200

polymer, molecular weight distribution = 1.12, Mn = 8200

Conditions
ConditionsYield
With 4,4'-dicyano-4,4'-azo-di-valeric acid In water at 75℃; for 12h;93.2%
1-indene
95-13-6

1-indene

4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

C22H21NO2S2

C22H21NO2S2

Conditions
ConditionsYield
With fac-tris(2-phenylpyridinato-N,C2')iridium(III) In dimethyl sulfoxide at 20℃; for 36h; Inert atmosphere; Irradiation; Sealed tube;93%
acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

C17H19NO4S2

C17H19NO4S2

Conditions
ConditionsYield
With pheophorbide A In dimethyl sulfoxide at 20℃; for 20h; Sealed tube; Inert atmosphere; Irradiation;92%
bis(2-hydroxyethyl) disulfide
1892-29-1

bis(2-hydroxyethyl) disulfide

4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

C30H32N2O4S6

C30H32N2O4S6

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h; Inert atmosphere;83.9%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h; Inert atmosphere;65.3%
3,3,4,4-tetrafluoro-butane sultone
1384119-19-0

3,3,4,4-tetrafluoro-butane sultone

5-phenyl-5H-dibenzo[b,d]thiophen-5-ium bromide

5-phenyl-5H-dibenzo[b,d]thiophen-5-ium bromide

4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

C17H16F4NO5S3(1-)*C18H13S(1+)

C17H16F4NO5S3(1-)*C18H13S(1+)

Conditions
ConditionsYield
Stage #1: 4-cyano-4-(thiobenzoylthio)pentanoic acid With potassium hydride In tetrahydrofuran Inert atmosphere;
Stage #2: 3,3,4,4-tetrafluoro-butane sultone In tetrahydrofuran at 20℃; for 2h;
Stage #3: 5-phenyl-5H-dibenzo[b,d]thiophen-5-ium bromide In dichloromethane; water at 20℃; for 12h;
83.7%
Stage #1: 4-cyano-4-(thiobenzoylthio)pentanoic acid With potassium hydride In tetrahydrofuran for 0.0833333h; Inert atmosphere;
Stage #2: 3,3,4,4-tetrafluoro-butane sultone In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;
Stage #3: 5-phenyl-5H-dibenzo[b,d]thiophen-5-ium bromide In water at 20℃; Inert atmosphere;
83.7%
2-nitro-5-(2-propargyloxy)benzyl alcohol
1144029-01-5

2-nitro-5-(2-propargyloxy)benzyl alcohol

4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

2-nitro-5-(2-propynyloxy)benzyl 4-cyano-4-(phenylcarbonothioylthio)pentanoate
1318075-32-9

2-nitro-5-(2-propynyloxy)benzyl 4-cyano-4-(phenylcarbonothioylthio)pentanoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 16h;83%
2-(2-(2-(2-(pyridin-2-yldisulfanyl)ethoxy)ethoxy)ethoxy)ethan-1-ol
851961-99-4

2-(2-(2-(2-(pyridin-2-yldisulfanyl)ethoxy)ethoxy)ethoxy)ethan-1-ol

4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

C26H32N2O5S4

C26H32N2O5S4

Conditions
ConditionsYield
Stage #1: 2-(2-(2-(2-(pyridin-2-yldisulfanyl)ethoxy)ethoxy)ethoxy)ethan-1-ol; 4-cyano-4-(thiobenzoylthio)pentanoic acid With dmap In dichloromethane at 0℃; for 0.5h;
Stage #2: With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 5h;
81%
4,4'-dicyano-4,4'-azo-di-valeric acid
2638-94-0

4,4'-dicyano-4,4'-azo-di-valeric acid

2'-(2''-methylacryolyloxy)ethyl-β-D-galactopyranoside
21698-14-6

2'-(2''-methylacryolyloxy)ethyl-β-D-galactopyranoside

4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

poly[2-(β-D-galactosyloxy)ethyl methacrylate], Mn (SEC) 24100, PDI (SEC) 1.09; monomer(s): 2-(β-D-galactosyloxy)ethyl methacrylate; 4,4-azobis(4-cyanopentanoic acid); 4-(cyanopentanoic acid)-4-dithiobenzoate

poly[2-(β-D-galactosyloxy)ethyl methacrylate], Mn (SEC) 24100, PDI (SEC) 1.09; monomer(s): 2-(β-D-galactosyloxy)ethyl methacrylate; 4,4-azobis(4-cyanopentanoic acid); 4-(cyanopentanoic acid)-4-dithiobenzoate

Conditions
ConditionsYield
In ethanol; water at 70℃; for 3h;80%
propargyl alcohol
107-19-7

propargyl alcohol

4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

4-cyano-4-((thiobenzoyl)sulfanyl)pentanoic propargyl ester
1075252-15-1

4-cyano-4-((thiobenzoyl)sulfanyl)pentanoic propargyl ester

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 25℃; Steglich Esterification;80%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; Inert atmosphere;75%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 19h;62%
2-methyl-acrylic acid 3-dimethylamino-propyl amide
5205-93-6

2-methyl-acrylic acid 3-dimethylamino-propyl amide

4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

poly(N-[3-(dimethylamino)propyl]methacrylamide), terminated with 4-carboxy-2-cyanobutyl-2-yl and thiobenzoylsulfanyl units, product of RAFT polymerization; monomer(s): N-[3-(dimethylamino)propyl]methacrylamide; 4-carboxy-2-cyanobutyl-2-yl dithiobenzoate

poly(N-[3-(dimethylamino)propyl]methacrylamide), terminated with 4-carboxy-2-cyanobutyl-2-yl and thiobenzoylsulfanyl units, product of RAFT polymerization; monomer(s): N-[3-(dimethylamino)propyl]methacrylamide; 4-carboxy-2-cyanobutyl-2-yl dithiobenzoate

Conditions
ConditionsYield
With hydrogenchloride; 4,4'-dicyano-4,4'-azo-di-valeric acid In acetate buffer at 70℃; for 1h; pH=5;78.77%
2,3,4,5,6-pentafluorophenol
771-61-9

2,3,4,5,6-pentafluorophenol

4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

pentafluorophenyl 4-cyano-4-((phenylcarbonothioyl)thio)pentanoate
1160527-68-3

pentafluorophenyl 4-cyano-4-((phenylcarbonothioyl)thio)pentanoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 2h;76%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃;76%
With dmap; diisopropyl-carbodiimide In dichloromethane at 0℃;30%
2-methyl-2-propenoic acid 2-hydroxyethyl ester
868-77-9

2-methyl-2-propenoic acid 2-hydroxyethyl ester

4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

2-(methacryloyloxy)ethyl 4-cyano-4-(phenylcarbonothioylthio)pentanoate
1361105-67-0

2-(methacryloyloxy)ethyl 4-cyano-4-(phenylcarbonothioylthio)pentanoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In toluene at 20℃; for 12h;75%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 24h; Inert atmosphere;69.2%
4-(2-hydroxy-ethyl)-10-oxa-4-aza-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione
32620-90-9

4-(2-hydroxy-ethyl)-10-oxa-4-aza-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione

4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

C23H22N2O5S2

C23H22N2O5S2

Conditions
ConditionsYield
Stage #1: 4-(2-hydroxy-ethyl)-10-oxa-4-aza-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione; 4-cyano-4-(thiobenzoylthio)pentanoic acid With dmap; ethyl cyanoglyoxylate-2-oxime In acetonitrile for 0.0833333h; Schlenk technique;
Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 0 - 20℃; for 18h; Schlenk technique;
73%

201611-92-9Relevant articles and documents

Visible-light degradable polymer coated hollow mesoporous silica nanoparticles for controlled drug release and cell imaging

Yang, Shun,Li, Najun,Chen, Dongyun,Qi, Xiuxiu,Xu, Yujie,Xu, Ying,Xu, Qingfeng,Li, Hua,Lu, Jianmei

, p. 4628 - 4636 (2013)

A core-shell nanocomposite based on photo-degradable polymer coated hollow mesoporous silica nanoparticles (HMS) was successfully prepared for targeted drug delivery and visible-light triggered release, as well as fluorescence cell imaging. The HMS nanoparticles were first modified by the long-chain hydrocarbon octadecyltrimethoxysilane (C18) and fluorescent agent Rhodamine B isothiocyanate (RITC), and then encapsulated by a photodegradable amphiphilic copolymer via a self-assembly process. The obtained nanocarrier showed a high drug loading content due to the hollow core and mesopores of the HMS and could target folic acid receptor over-expressed tumor cells efficiently for conjugating folic acid (FA) in the amphiphilic polymer. The drug release could be triggered by the irradiation of green light (500-540 nm) due to the photodegradation of amphiphilic copolymer coated on the HMS. Furthermore, the targeted drug delivery and controlled release processes could be tracked by fluorescence imaging for the doping of RITC on the HMS. The In vitro results suggested that a smart visible light responsive drug delivery system was successfully prepared for the potential applications of cancer diagnosis and therapy.

Fine-tuning the transition temperature of a stimuli-responsive polymer by a simple blending procedure

Fernandez-Trillo, Francisco,Van Hest, Jan C. M.,Thies, Jens C.,Michon, Thierry,Weberskirch, Ralf,Cameron, Neil R.

, p. 2230 - 2232 (2008)

Binary mixtures of well-defined, stimuli-responsive elastin-based side-chain polymers show a single transition temperature that depends on blend composition. The Royal Society of Chemistry.

Visible-Light-Driven MADIX Polymerisation via a Reusable, Low-Cost, and Non-Toxic Bismuth Oxide Photocatalyst

Hakobyan, Karen,Gegenhuber, Thomas,McErlean, Christopher S. P.,Müllner, Markus

supporting information, p. 1828 - 1832 (2019/01/14)

The continuous amalgamation of photocatalysis into existing reversible deactivation radical polymerisation (RDRP) processes has initiated a rapidly propagating area of polymer research in recent years. We introduce bismuth oxide (Bi2O3) as a heterogeneous photocatalyst for polymerisations, operating at room temperature with visible light. We demonstrate formidable control over degenerative chain-transfer polymerisations, such as macromolecular design by interchange of xanthate (MADIX) and reversible addition-fragmentation chain-transfer (RAFT) polymerisation. We achieved narrow molecular weight distributions and attribute the excellent temporal control of a photo-induced electron transfer (PET) process. This methodology was employed to synthesise diblock copolymers combining differently activated monomers. The Bi2O3 catalyst system has the additional benefits of low toxicity, reusability, low-cost, and ease of removal from the reaction mixture.

A new selenium-based RAFT agent for surface-initiated RAFT polymerization of 4-vinylpyridine

Demirci, Serkan,Kinali-Demirci, Selin,Caykara, Tuncer

, p. 5345 - 5350 (2013/09/23)

A new selenium-based reversible addition-fragmentation chain transfer (RAFT) agent, 4-cyanopentanoic acid diselenobenzoate (RAFT-Se), was synthesized and utilized in the surface-initiated RAFT polymerization of 4-vinylpyridine (4VP) on silicon substrate. The results indicate that the RAFT-Se can control the surface-initiated RAFT polymerization, as evidenced by the number-average molecular weight that increase linearly with monomer conversion, molecular weights that agreed well with the predicted values, and the relatively low polydispersity indexes. The surface-initiated RAFT polymerization with the RAFT-Se was the same polymerization mechanism as its analog, 4-cyanopentanoic acid dithiobenzoate (RAFT-S). The grafting density of the poly(4-vinylpyridine) brushes prepared in the presence of RAFT-Se (σRAFT-Se) and RAFT-S (σRAFT-S) was estimated to be about 0.51 and 0.66 chains/nm2, respectively. In addition, the end of polymer chains on silicon substrate contains selenium element which may be useful in biosensor applications.

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