Debromination of ATRP-made Wang soluble polymer supports
This article describes two convenient methods for removing the ω-terminal bromine atom of well-defined soluble polymer supports prepared by atom transfer radical polymerization (ATRP). The targeted soluble supports are linear polystyrene chains that contain an acid-labile p-alkoxybenzyl ester linker...
Ausführliche Beschreibung
Gespeichert in:
| Autor*in: |
Oswald, Laurence [verfasserIn] |
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| Format: |
E-Artikel |
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| Sprache: |
Englisch |
| Erschienen: |
2015transfer abstract |
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7 |
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| Übergeordnetes Werk: |
Enthalten in: Functional outcomes at 12 months for patients with traumatic brain injury, intracerebral haemorrhage and subarachnoid haemorrhage treated in an Australian neurocritical care unit: A prospective cohort study - Fitzgerald, Emily ELSEVIER, 2020, the international journal for the science and technology of polymers, Oxford |
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| Übergeordnetes Werk: |
volume:72 ; year:2015 ; day:18 ; month:08 ; pages:341-347 ; extent:7 |
| Links: |
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| DOI / URN: |
10.1016/j.polymer.2015.02.057 |
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ELV019008864 |
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| 264 | 1 | |c 2015transfer abstract | |
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| 520 | |a This article describes two convenient methods for removing the ω-terminal bromine atom of well-defined soluble polymer supports prepared by atom transfer radical polymerization (ATRP). The targeted soluble supports are linear polystyrene chains that contain an acid-labile p-alkoxybenzyl ester linker (i.e. Wang linker) at their α-chain end. These polymers are synthesized by ATRP using a fluorenylmethoxycarbonyl (Fmoc)-protected amino functional ATRP initiator, namely 3-(Fmoc-amino)propyl 2-bromoisobutyrate. After polymerization and before Wang functionalization, the bromine-atom of the ATRP-made soluble supports was removed. Two different debromination approaches were considered. The first one consists in reducing the terminal alkyl bromide in the presence of a trialkyltin hydride. This method can be applied directly in the ATRP medium at the end of the polymerization or can be performed on a purified polymer sample. The latter conditions were found to be more suitable. It was also observed that the use of tributyltin hydride in the absence of additional radical initiator led to the best results. Indeed, well-defined polymer supports with controlled chain-length, molecular weight distribution and fully dehalogenated chain-ends were obtained. The second dehalogenation approach consisted in removing the terminal bromide by nucleophilic substitution with sodium azide. Afterwards, the formed terminal azide group was reacted with 1-pentyne by copper-catalyzed azide-alkyne 1, 3-dipolar Huisgen cycloaddition. This method was also found to be valid for preparing bromine-free polystyrene supports. After ω-chain-end debromination, Fmoc-deprotection was performed on the α-chain-end and the resulting amine function was reacted with 4-(hydroxymethyl)phenoxyacetic acid. Further esterification of the Wang linker is also possible. | ||
| 520 | |a This article describes two convenient methods for removing the ω-terminal bromine atom of well-defined soluble polymer supports prepared by atom transfer radical polymerization (ATRP). The targeted soluble supports are linear polystyrene chains that contain an acid-labile p-alkoxybenzyl ester linker (i.e. Wang linker) at their α-chain end. These polymers are synthesized by ATRP using a fluorenylmethoxycarbonyl (Fmoc)-protected amino functional ATRP initiator, namely 3-(Fmoc-amino)propyl 2-bromoisobutyrate. After polymerization and before Wang functionalization, the bromine-atom of the ATRP-made soluble supports was removed. Two different debromination approaches were considered. The first one consists in reducing the terminal alkyl bromide in the presence of a trialkyltin hydride. This method can be applied directly in the ATRP medium at the end of the polymerization or can be performed on a purified polymer sample. The latter conditions were found to be more suitable. It was also observed that the use of tributyltin hydride in the absence of additional radical initiator led to the best results. Indeed, well-defined polymer supports with controlled chain-length, molecular weight distribution and fully dehalogenated chain-ends were obtained. The second dehalogenation approach consisted in removing the terminal bromide by nucleophilic substitution with sodium azide. Afterwards, the formed terminal azide group was reacted with 1-pentyne by copper-catalyzed azide-alkyne 1, 3-dipolar Huisgen cycloaddition. This method was also found to be valid for preparing bromine-free polystyrene supports. After ω-chain-end debromination, Fmoc-deprotection was performed on the α-chain-end and the resulting amine function was reacted with 4-(hydroxymethyl)phenoxyacetic acid. Further esterification of the Wang linker is also possible. | ||
| 650 | 7 | |a Controlled radical polymerization |2 Elsevier | |
| 650 | 7 | |a Soluble polymer supports |2 Elsevier | |
| 650 | 7 | |a Atom transfer radical polymerization |2 Elsevier | |
| 700 | 1 | |a Trinh, Thanh Tam |4 oth | |
| 700 | 1 | |a Chan-Seng, Delphine |4 oth | |
| 700 | 1 | |a Lutz, Jean-François |4 oth | |
| 773 | 0 | 8 | |i Enthalten in |n Elsevier Science |a Fitzgerald, Emily ELSEVIER |t Functional outcomes at 12 months for patients with traumatic brain injury, intracerebral haemorrhage and subarachnoid haemorrhage treated in an Australian neurocritical care unit: A prospective cohort study |d 2020 |d the international journal for the science and technology of polymers |g Oxford |w (DE-627)ELV005093368 |
| 773 | 1 | 8 | |g volume:72 |g year:2015 |g day:18 |g month:08 |g pages:341-347 |g extent:7 |
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10.1016/j.polymer.2015.02.057 doi GBV00000000000367.pica (DE-627)ELV019008864 (ELSEVIER)S0032-3861(15)00226-8 DE-627 ger DE-627 rakwb eng 610 VZ 44.63 bkl 44.69 bkl Oswald, Laurence verfasserin aut Debromination of ATRP-made Wang soluble polymer supports 2015transfer abstract 7 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier This article describes two convenient methods for removing the ω-terminal bromine atom of well-defined soluble polymer supports prepared by atom transfer radical polymerization (ATRP). The targeted soluble supports are linear polystyrene chains that contain an acid-labile p-alkoxybenzyl ester linker (i.e. Wang linker) at their α-chain end. These polymers are synthesized by ATRP using a fluorenylmethoxycarbonyl (Fmoc)-protected amino functional ATRP initiator, namely 3-(Fmoc-amino)propyl 2-bromoisobutyrate. After polymerization and before Wang functionalization, the bromine-atom of the ATRP-made soluble supports was removed. Two different debromination approaches were considered. The first one consists in reducing the terminal alkyl bromide in the presence of a trialkyltin hydride. This method can be applied directly in the ATRP medium at the end of the polymerization or can be performed on a purified polymer sample. The latter conditions were found to be more suitable. It was also observed that the use of tributyltin hydride in the absence of additional radical initiator led to the best results. Indeed, well-defined polymer supports with controlled chain-length, molecular weight distribution and fully dehalogenated chain-ends were obtained. The second dehalogenation approach consisted in removing the terminal bromide by nucleophilic substitution with sodium azide. Afterwards, the formed terminal azide group was reacted with 1-pentyne by copper-catalyzed azide-alkyne 1, 3-dipolar Huisgen cycloaddition. This method was also found to be valid for preparing bromine-free polystyrene supports. After ω-chain-end debromination, Fmoc-deprotection was performed on the α-chain-end and the resulting amine function was reacted with 4-(hydroxymethyl)phenoxyacetic acid. Further esterification of the Wang linker is also possible. This article describes two convenient methods for removing the ω-terminal bromine atom of well-defined soluble polymer supports prepared by atom transfer radical polymerization (ATRP). The targeted soluble supports are linear polystyrene chains that contain an acid-labile p-alkoxybenzyl ester linker (i.e. Wang linker) at their α-chain end. These polymers are synthesized by ATRP using a fluorenylmethoxycarbonyl (Fmoc)-protected amino functional ATRP initiator, namely 3-(Fmoc-amino)propyl 2-bromoisobutyrate. After polymerization and before Wang functionalization, the bromine-atom of the ATRP-made soluble supports was removed. Two different debromination approaches were considered. The first one consists in reducing the terminal alkyl bromide in the presence of a trialkyltin hydride. This method can be applied directly in the ATRP medium at the end of the polymerization or can be performed on a purified polymer sample. The latter conditions were found to be more suitable. It was also observed that the use of tributyltin hydride in the absence of additional radical initiator led to the best results. Indeed, well-defined polymer supports with controlled chain-length, molecular weight distribution and fully dehalogenated chain-ends were obtained. The second dehalogenation approach consisted in removing the terminal bromide by nucleophilic substitution with sodium azide. Afterwards, the formed terminal azide group was reacted with 1-pentyne by copper-catalyzed azide-alkyne 1, 3-dipolar Huisgen cycloaddition. This method was also found to be valid for preparing bromine-free polystyrene supports. After ω-chain-end debromination, Fmoc-deprotection was performed on the α-chain-end and the resulting amine function was reacted with 4-(hydroxymethyl)phenoxyacetic acid. Further esterification of the Wang linker is also possible. Controlled radical polymerization Elsevier Soluble polymer supports Elsevier Atom transfer radical polymerization Elsevier Trinh, Thanh Tam oth Chan-Seng, Delphine oth Lutz, Jean-François oth Enthalten in Elsevier Science Fitzgerald, Emily ELSEVIER Functional outcomes at 12 months for patients with traumatic brain injury, intracerebral haemorrhage and subarachnoid haemorrhage treated in an Australian neurocritical care unit: A prospective cohort study 2020 the international journal for the science and technology of polymers Oxford (DE-627)ELV005093368 volume:72 year:2015 day:18 month:08 pages:341-347 extent:7 https://doi.org/10.1016/j.polymer.2015.02.057 Volltext GBV_USEFLAG_U GBV_ELV SYSFLAG_U SSG-OLC-PHA 44.63 Krankenpflege VZ 44.69 Intensivmedizin VZ AR 72 2015 18 0818 341-347 7 |
| spelling |
10.1016/j.polymer.2015.02.057 doi GBV00000000000367.pica (DE-627)ELV019008864 (ELSEVIER)S0032-3861(15)00226-8 DE-627 ger DE-627 rakwb eng 610 VZ 44.63 bkl 44.69 bkl Oswald, Laurence verfasserin aut Debromination of ATRP-made Wang soluble polymer supports 2015transfer abstract 7 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier This article describes two convenient methods for removing the ω-terminal bromine atom of well-defined soluble polymer supports prepared by atom transfer radical polymerization (ATRP). The targeted soluble supports are linear polystyrene chains that contain an acid-labile p-alkoxybenzyl ester linker (i.e. Wang linker) at their α-chain end. These polymers are synthesized by ATRP using a fluorenylmethoxycarbonyl (Fmoc)-protected amino functional ATRP initiator, namely 3-(Fmoc-amino)propyl 2-bromoisobutyrate. After polymerization and before Wang functionalization, the bromine-atom of the ATRP-made soluble supports was removed. Two different debromination approaches were considered. The first one consists in reducing the terminal alkyl bromide in the presence of a trialkyltin hydride. This method can be applied directly in the ATRP medium at the end of the polymerization or can be performed on a purified polymer sample. The latter conditions were found to be more suitable. It was also observed that the use of tributyltin hydride in the absence of additional radical initiator led to the best results. Indeed, well-defined polymer supports with controlled chain-length, molecular weight distribution and fully dehalogenated chain-ends were obtained. The second dehalogenation approach consisted in removing the terminal bromide by nucleophilic substitution with sodium azide. Afterwards, the formed terminal azide group was reacted with 1-pentyne by copper-catalyzed azide-alkyne 1, 3-dipolar Huisgen cycloaddition. This method was also found to be valid for preparing bromine-free polystyrene supports. After ω-chain-end debromination, Fmoc-deprotection was performed on the α-chain-end and the resulting amine function was reacted with 4-(hydroxymethyl)phenoxyacetic acid. Further esterification of the Wang linker is also possible. This article describes two convenient methods for removing the ω-terminal bromine atom of well-defined soluble polymer supports prepared by atom transfer radical polymerization (ATRP). The targeted soluble supports are linear polystyrene chains that contain an acid-labile p-alkoxybenzyl ester linker (i.e. Wang linker) at their α-chain end. These polymers are synthesized by ATRP using a fluorenylmethoxycarbonyl (Fmoc)-protected amino functional ATRP initiator, namely 3-(Fmoc-amino)propyl 2-bromoisobutyrate. After polymerization and before Wang functionalization, the bromine-atom of the ATRP-made soluble supports was removed. Two different debromination approaches were considered. The first one consists in reducing the terminal alkyl bromide in the presence of a trialkyltin hydride. This method can be applied directly in the ATRP medium at the end of the polymerization or can be performed on a purified polymer sample. The latter conditions were found to be more suitable. It was also observed that the use of tributyltin hydride in the absence of additional radical initiator led to the best results. Indeed, well-defined polymer supports with controlled chain-length, molecular weight distribution and fully dehalogenated chain-ends were obtained. The second dehalogenation approach consisted in removing the terminal bromide by nucleophilic substitution with sodium azide. Afterwards, the formed terminal azide group was reacted with 1-pentyne by copper-catalyzed azide-alkyne 1, 3-dipolar Huisgen cycloaddition. This method was also found to be valid for preparing bromine-free polystyrene supports. After ω-chain-end debromination, Fmoc-deprotection was performed on the α-chain-end and the resulting amine function was reacted with 4-(hydroxymethyl)phenoxyacetic acid. Further esterification of the Wang linker is also possible. Controlled radical polymerization Elsevier Soluble polymer supports Elsevier Atom transfer radical polymerization Elsevier Trinh, Thanh Tam oth Chan-Seng, Delphine oth Lutz, Jean-François oth Enthalten in Elsevier Science Fitzgerald, Emily ELSEVIER Functional outcomes at 12 months for patients with traumatic brain injury, intracerebral haemorrhage and subarachnoid haemorrhage treated in an Australian neurocritical care unit: A prospective cohort study 2020 the international journal for the science and technology of polymers Oxford (DE-627)ELV005093368 volume:72 year:2015 day:18 month:08 pages:341-347 extent:7 https://doi.org/10.1016/j.polymer.2015.02.057 Volltext GBV_USEFLAG_U GBV_ELV SYSFLAG_U SSG-OLC-PHA 44.63 Krankenpflege VZ 44.69 Intensivmedizin VZ AR 72 2015 18 0818 341-347 7 |
| allfields_unstemmed |
10.1016/j.polymer.2015.02.057 doi GBV00000000000367.pica (DE-627)ELV019008864 (ELSEVIER)S0032-3861(15)00226-8 DE-627 ger DE-627 rakwb eng 610 VZ 44.63 bkl 44.69 bkl Oswald, Laurence verfasserin aut Debromination of ATRP-made Wang soluble polymer supports 2015transfer abstract 7 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier This article describes two convenient methods for removing the ω-terminal bromine atom of well-defined soluble polymer supports prepared by atom transfer radical polymerization (ATRP). The targeted soluble supports are linear polystyrene chains that contain an acid-labile p-alkoxybenzyl ester linker (i.e. Wang linker) at their α-chain end. These polymers are synthesized by ATRP using a fluorenylmethoxycarbonyl (Fmoc)-protected amino functional ATRP initiator, namely 3-(Fmoc-amino)propyl 2-bromoisobutyrate. After polymerization and before Wang functionalization, the bromine-atom of the ATRP-made soluble supports was removed. Two different debromination approaches were considered. The first one consists in reducing the terminal alkyl bromide in the presence of a trialkyltin hydride. This method can be applied directly in the ATRP medium at the end of the polymerization or can be performed on a purified polymer sample. The latter conditions were found to be more suitable. It was also observed that the use of tributyltin hydride in the absence of additional radical initiator led to the best results. Indeed, well-defined polymer supports with controlled chain-length, molecular weight distribution and fully dehalogenated chain-ends were obtained. The second dehalogenation approach consisted in removing the terminal bromide by nucleophilic substitution with sodium azide. Afterwards, the formed terminal azide group was reacted with 1-pentyne by copper-catalyzed azide-alkyne 1, 3-dipolar Huisgen cycloaddition. This method was also found to be valid for preparing bromine-free polystyrene supports. After ω-chain-end debromination, Fmoc-deprotection was performed on the α-chain-end and the resulting amine function was reacted with 4-(hydroxymethyl)phenoxyacetic acid. Further esterification of the Wang linker is also possible. This article describes two convenient methods for removing the ω-terminal bromine atom of well-defined soluble polymer supports prepared by atom transfer radical polymerization (ATRP). The targeted soluble supports are linear polystyrene chains that contain an acid-labile p-alkoxybenzyl ester linker (i.e. Wang linker) at their α-chain end. These polymers are synthesized by ATRP using a fluorenylmethoxycarbonyl (Fmoc)-protected amino functional ATRP initiator, namely 3-(Fmoc-amino)propyl 2-bromoisobutyrate. After polymerization and before Wang functionalization, the bromine-atom of the ATRP-made soluble supports was removed. Two different debromination approaches were considered. The first one consists in reducing the terminal alkyl bromide in the presence of a trialkyltin hydride. This method can be applied directly in the ATRP medium at the end of the polymerization or can be performed on a purified polymer sample. The latter conditions were found to be more suitable. It was also observed that the use of tributyltin hydride in the absence of additional radical initiator led to the best results. Indeed, well-defined polymer supports with controlled chain-length, molecular weight distribution and fully dehalogenated chain-ends were obtained. The second dehalogenation approach consisted in removing the terminal bromide by nucleophilic substitution with sodium azide. Afterwards, the formed terminal azide group was reacted with 1-pentyne by copper-catalyzed azide-alkyne 1, 3-dipolar Huisgen cycloaddition. This method was also found to be valid for preparing bromine-free polystyrene supports. After ω-chain-end debromination, Fmoc-deprotection was performed on the α-chain-end and the resulting amine function was reacted with 4-(hydroxymethyl)phenoxyacetic acid. Further esterification of the Wang linker is also possible. Controlled radical polymerization Elsevier Soluble polymer supports Elsevier Atom transfer radical polymerization Elsevier Trinh, Thanh Tam oth Chan-Seng, Delphine oth Lutz, Jean-François oth Enthalten in Elsevier Science Fitzgerald, Emily ELSEVIER Functional outcomes at 12 months for patients with traumatic brain injury, intracerebral haemorrhage and subarachnoid haemorrhage treated in an Australian neurocritical care unit: A prospective cohort study 2020 the international journal for the science and technology of polymers Oxford (DE-627)ELV005093368 volume:72 year:2015 day:18 month:08 pages:341-347 extent:7 https://doi.org/10.1016/j.polymer.2015.02.057 Volltext GBV_USEFLAG_U GBV_ELV SYSFLAG_U SSG-OLC-PHA 44.63 Krankenpflege VZ 44.69 Intensivmedizin VZ AR 72 2015 18 0818 341-347 7 |
| allfieldsGer |
10.1016/j.polymer.2015.02.057 doi GBV00000000000367.pica (DE-627)ELV019008864 (ELSEVIER)S0032-3861(15)00226-8 DE-627 ger DE-627 rakwb eng 610 VZ 44.63 bkl 44.69 bkl Oswald, Laurence verfasserin aut Debromination of ATRP-made Wang soluble polymer supports 2015transfer abstract 7 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier This article describes two convenient methods for removing the ω-terminal bromine atom of well-defined soluble polymer supports prepared by atom transfer radical polymerization (ATRP). The targeted soluble supports are linear polystyrene chains that contain an acid-labile p-alkoxybenzyl ester linker (i.e. Wang linker) at their α-chain end. These polymers are synthesized by ATRP using a fluorenylmethoxycarbonyl (Fmoc)-protected amino functional ATRP initiator, namely 3-(Fmoc-amino)propyl 2-bromoisobutyrate. After polymerization and before Wang functionalization, the bromine-atom of the ATRP-made soluble supports was removed. Two different debromination approaches were considered. The first one consists in reducing the terminal alkyl bromide in the presence of a trialkyltin hydride. This method can be applied directly in the ATRP medium at the end of the polymerization or can be performed on a purified polymer sample. The latter conditions were found to be more suitable. It was also observed that the use of tributyltin hydride in the absence of additional radical initiator led to the best results. Indeed, well-defined polymer supports with controlled chain-length, molecular weight distribution and fully dehalogenated chain-ends were obtained. The second dehalogenation approach consisted in removing the terminal bromide by nucleophilic substitution with sodium azide. Afterwards, the formed terminal azide group was reacted with 1-pentyne by copper-catalyzed azide-alkyne 1, 3-dipolar Huisgen cycloaddition. This method was also found to be valid for preparing bromine-free polystyrene supports. After ω-chain-end debromination, Fmoc-deprotection was performed on the α-chain-end and the resulting amine function was reacted with 4-(hydroxymethyl)phenoxyacetic acid. Further esterification of the Wang linker is also possible. This article describes two convenient methods for removing the ω-terminal bromine atom of well-defined soluble polymer supports prepared by atom transfer radical polymerization (ATRP). The targeted soluble supports are linear polystyrene chains that contain an acid-labile p-alkoxybenzyl ester linker (i.e. Wang linker) at their α-chain end. These polymers are synthesized by ATRP using a fluorenylmethoxycarbonyl (Fmoc)-protected amino functional ATRP initiator, namely 3-(Fmoc-amino)propyl 2-bromoisobutyrate. After polymerization and before Wang functionalization, the bromine-atom of the ATRP-made soluble supports was removed. Two different debromination approaches were considered. The first one consists in reducing the terminal alkyl bromide in the presence of a trialkyltin hydride. This method can be applied directly in the ATRP medium at the end of the polymerization or can be performed on a purified polymer sample. The latter conditions were found to be more suitable. It was also observed that the use of tributyltin hydride in the absence of additional radical initiator led to the best results. Indeed, well-defined polymer supports with controlled chain-length, molecular weight distribution and fully dehalogenated chain-ends were obtained. The second dehalogenation approach consisted in removing the terminal bromide by nucleophilic substitution with sodium azide. Afterwards, the formed terminal azide group was reacted with 1-pentyne by copper-catalyzed azide-alkyne 1, 3-dipolar Huisgen cycloaddition. This method was also found to be valid for preparing bromine-free polystyrene supports. After ω-chain-end debromination, Fmoc-deprotection was performed on the α-chain-end and the resulting amine function was reacted with 4-(hydroxymethyl)phenoxyacetic acid. Further esterification of the Wang linker is also possible. Controlled radical polymerization Elsevier Soluble polymer supports Elsevier Atom transfer radical polymerization Elsevier Trinh, Thanh Tam oth Chan-Seng, Delphine oth Lutz, Jean-François oth Enthalten in Elsevier Science Fitzgerald, Emily ELSEVIER Functional outcomes at 12 months for patients with traumatic brain injury, intracerebral haemorrhage and subarachnoid haemorrhage treated in an Australian neurocritical care unit: A prospective cohort study 2020 the international journal for the science and technology of polymers Oxford (DE-627)ELV005093368 volume:72 year:2015 day:18 month:08 pages:341-347 extent:7 https://doi.org/10.1016/j.polymer.2015.02.057 Volltext GBV_USEFLAG_U GBV_ELV SYSFLAG_U SSG-OLC-PHA 44.63 Krankenpflege VZ 44.69 Intensivmedizin VZ AR 72 2015 18 0818 341-347 7 |
| allfieldsSound |
10.1016/j.polymer.2015.02.057 doi GBV00000000000367.pica (DE-627)ELV019008864 (ELSEVIER)S0032-3861(15)00226-8 DE-627 ger DE-627 rakwb eng 610 VZ 44.63 bkl 44.69 bkl Oswald, Laurence verfasserin aut Debromination of ATRP-made Wang soluble polymer supports 2015transfer abstract 7 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier This article describes two convenient methods for removing the ω-terminal bromine atom of well-defined soluble polymer supports prepared by atom transfer radical polymerization (ATRP). The targeted soluble supports are linear polystyrene chains that contain an acid-labile p-alkoxybenzyl ester linker (i.e. Wang linker) at their α-chain end. These polymers are synthesized by ATRP using a fluorenylmethoxycarbonyl (Fmoc)-protected amino functional ATRP initiator, namely 3-(Fmoc-amino)propyl 2-bromoisobutyrate. After polymerization and before Wang functionalization, the bromine-atom of the ATRP-made soluble supports was removed. Two different debromination approaches were considered. The first one consists in reducing the terminal alkyl bromide in the presence of a trialkyltin hydride. This method can be applied directly in the ATRP medium at the end of the polymerization or can be performed on a purified polymer sample. The latter conditions were found to be more suitable. It was also observed that the use of tributyltin hydride in the absence of additional radical initiator led to the best results. Indeed, well-defined polymer supports with controlled chain-length, molecular weight distribution and fully dehalogenated chain-ends were obtained. The second dehalogenation approach consisted in removing the terminal bromide by nucleophilic substitution with sodium azide. Afterwards, the formed terminal azide group was reacted with 1-pentyne by copper-catalyzed azide-alkyne 1, 3-dipolar Huisgen cycloaddition. This method was also found to be valid for preparing bromine-free polystyrene supports. After ω-chain-end debromination, Fmoc-deprotection was performed on the α-chain-end and the resulting amine function was reacted with 4-(hydroxymethyl)phenoxyacetic acid. Further esterification of the Wang linker is also possible. This article describes two convenient methods for removing the ω-terminal bromine atom of well-defined soluble polymer supports prepared by atom transfer radical polymerization (ATRP). The targeted soluble supports are linear polystyrene chains that contain an acid-labile p-alkoxybenzyl ester linker (i.e. Wang linker) at their α-chain end. These polymers are synthesized by ATRP using a fluorenylmethoxycarbonyl (Fmoc)-protected amino functional ATRP initiator, namely 3-(Fmoc-amino)propyl 2-bromoisobutyrate. After polymerization and before Wang functionalization, the bromine-atom of the ATRP-made soluble supports was removed. Two different debromination approaches were considered. The first one consists in reducing the terminal alkyl bromide in the presence of a trialkyltin hydride. This method can be applied directly in the ATRP medium at the end of the polymerization or can be performed on a purified polymer sample. The latter conditions were found to be more suitable. It was also observed that the use of tributyltin hydride in the absence of additional radical initiator led to the best results. Indeed, well-defined polymer supports with controlled chain-length, molecular weight distribution and fully dehalogenated chain-ends were obtained. The second dehalogenation approach consisted in removing the terminal bromide by nucleophilic substitution with sodium azide. Afterwards, the formed terminal azide group was reacted with 1-pentyne by copper-catalyzed azide-alkyne 1, 3-dipolar Huisgen cycloaddition. This method was also found to be valid for preparing bromine-free polystyrene supports. After ω-chain-end debromination, Fmoc-deprotection was performed on the α-chain-end and the resulting amine function was reacted with 4-(hydroxymethyl)phenoxyacetic acid. Further esterification of the Wang linker is also possible. Controlled radical polymerization Elsevier Soluble polymer supports Elsevier Atom transfer radical polymerization Elsevier Trinh, Thanh Tam oth Chan-Seng, Delphine oth Lutz, Jean-François oth Enthalten in Elsevier Science Fitzgerald, Emily ELSEVIER Functional outcomes at 12 months for patients with traumatic brain injury, intracerebral haemorrhage and subarachnoid haemorrhage treated in an Australian neurocritical care unit: A prospective cohort study 2020 the international journal for the science and technology of polymers Oxford (DE-627)ELV005093368 volume:72 year:2015 day:18 month:08 pages:341-347 extent:7 https://doi.org/10.1016/j.polymer.2015.02.057 Volltext GBV_USEFLAG_U GBV_ELV SYSFLAG_U SSG-OLC-PHA 44.63 Krankenpflege VZ 44.69 Intensivmedizin VZ AR 72 2015 18 0818 341-347 7 |
| language |
English |
| source |
Enthalten in Functional outcomes at 12 months for patients with traumatic brain injury, intracerebral haemorrhage and subarachnoid haemorrhage treated in an Australian neurocritical care unit: A prospective cohort study Oxford volume:72 year:2015 day:18 month:08 pages:341-347 extent:7 |
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This article describes two convenient methods for removing the ω-terminal bromine atom of well-defined soluble polymer supports prepared by atom transfer radical polymerization (ATRP). The targeted soluble supports are linear polystyrene chains that contain an acid-labile p-alkoxybenzyl ester linker (i.e. Wang linker) at their α-chain end. These polymers are synthesized by ATRP using a fluorenylmethoxycarbonyl (Fmoc)-protected amino functional ATRP initiator, namely 3-(Fmoc-amino)propyl 2-bromoisobutyrate. After polymerization and before Wang functionalization, the bromine-atom of the ATRP-made soluble supports was removed. Two different debromination approaches were considered. The first one consists in reducing the terminal alkyl bromide in the presence of a trialkyltin hydride. This method can be applied directly in the ATRP medium at the end of the polymerization or can be performed on a purified polymer sample. The latter conditions were found to be more suitable. It was also observed that the use of tributyltin hydride in the absence of additional radical initiator led to the best results. Indeed, well-defined polymer supports with controlled chain-length, molecular weight distribution and fully dehalogenated chain-ends were obtained. The second dehalogenation approach consisted in removing the terminal bromide by nucleophilic substitution with sodium azide. Afterwards, the formed terminal azide group was reacted with 1-pentyne by copper-catalyzed azide-alkyne 1, 3-dipolar Huisgen cycloaddition. This method was also found to be valid for preparing bromine-free polystyrene supports. After ω-chain-end debromination, Fmoc-deprotection was performed on the α-chain-end and the resulting amine function was reacted with 4-(hydroxymethyl)phenoxyacetic acid. Further esterification of the Wang linker is also possible. |
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This article describes two convenient methods for removing the ω-terminal bromine atom of well-defined soluble polymer supports prepared by atom transfer radical polymerization (ATRP). The targeted soluble supports are linear polystyrene chains that contain an acid-labile p-alkoxybenzyl ester linker (i.e. Wang linker) at their α-chain end. These polymers are synthesized by ATRP using a fluorenylmethoxycarbonyl (Fmoc)-protected amino functional ATRP initiator, namely 3-(Fmoc-amino)propyl 2-bromoisobutyrate. After polymerization and before Wang functionalization, the bromine-atom of the ATRP-made soluble supports was removed. Two different debromination approaches were considered. The first one consists in reducing the terminal alkyl bromide in the presence of a trialkyltin hydride. This method can be applied directly in the ATRP medium at the end of the polymerization or can be performed on a purified polymer sample. The latter conditions were found to be more suitable. It was also observed that the use of tributyltin hydride in the absence of additional radical initiator led to the best results. Indeed, well-defined polymer supports with controlled chain-length, molecular weight distribution and fully dehalogenated chain-ends were obtained. The second dehalogenation approach consisted in removing the terminal bromide by nucleophilic substitution with sodium azide. Afterwards, the formed terminal azide group was reacted with 1-pentyne by copper-catalyzed azide-alkyne 1, 3-dipolar Huisgen cycloaddition. This method was also found to be valid for preparing bromine-free polystyrene supports. After ω-chain-end debromination, Fmoc-deprotection was performed on the α-chain-end and the resulting amine function was reacted with 4-(hydroxymethyl)phenoxyacetic acid. Further esterification of the Wang linker is also possible. |
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This article describes two convenient methods for removing the ω-terminal bromine atom of well-defined soluble polymer supports prepared by atom transfer radical polymerization (ATRP). The targeted soluble supports are linear polystyrene chains that contain an acid-labile p-alkoxybenzyl ester linker (i.e. Wang linker) at their α-chain end. These polymers are synthesized by ATRP using a fluorenylmethoxycarbonyl (Fmoc)-protected amino functional ATRP initiator, namely 3-(Fmoc-amino)propyl 2-bromoisobutyrate. After polymerization and before Wang functionalization, the bromine-atom of the ATRP-made soluble supports was removed. Two different debromination approaches were considered. The first one consists in reducing the terminal alkyl bromide in the presence of a trialkyltin hydride. This method can be applied directly in the ATRP medium at the end of the polymerization or can be performed on a purified polymer sample. The latter conditions were found to be more suitable. It was also observed that the use of tributyltin hydride in the absence of additional radical initiator led to the best results. Indeed, well-defined polymer supports with controlled chain-length, molecular weight distribution and fully dehalogenated chain-ends were obtained. The second dehalogenation approach consisted in removing the terminal bromide by nucleophilic substitution with sodium azide. Afterwards, the formed terminal azide group was reacted with 1-pentyne by copper-catalyzed azide-alkyne 1, 3-dipolar Huisgen cycloaddition. This method was also found to be valid for preparing bromine-free polystyrene supports. After ω-chain-end debromination, Fmoc-deprotection was performed on the α-chain-end and the resulting amine function was reacted with 4-(hydroxymethyl)phenoxyacetic acid. Further esterification of the Wang linker is also possible. |
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The targeted soluble supports are linear polystyrene chains that contain an acid-labile p-alkoxybenzyl ester linker (i.e. Wang linker) at their α-chain end. These polymers are synthesized by ATRP using a fluorenylmethoxycarbonyl (Fmoc)-protected amino functional ATRP initiator, namely 3-(Fmoc-amino)propyl 2-bromoisobutyrate. After polymerization and before Wang functionalization, the bromine-atom of the ATRP-made soluble supports was removed. Two different debromination approaches were considered. The first one consists in reducing the terminal alkyl bromide in the presence of a trialkyltin hydride. This method can be applied directly in the ATRP medium at the end of the polymerization or can be performed on a purified polymer sample. The latter conditions were found to be more suitable. It was also observed that the use of tributyltin hydride in the absence of additional radical initiator led to the best results. Indeed, well-defined polymer supports with controlled chain-length, molecular weight distribution and fully dehalogenated chain-ends were obtained. The second dehalogenation approach consisted in removing the terminal bromide by nucleophilic substitution with sodium azide. Afterwards, the formed terminal azide group was reacted with 1-pentyne by copper-catalyzed azide-alkyne 1, 3-dipolar Huisgen cycloaddition. This method was also found to be valid for preparing bromine-free polystyrene supports. After ω-chain-end debromination, Fmoc-deprotection was performed on the α-chain-end and the resulting amine function was reacted with 4-(hydroxymethyl)phenoxyacetic acid. Further esterification of the Wang linker is also possible.</subfield></datafield><datafield tag="650" ind1=" " ind2="7"><subfield code="a">Controlled radical polymerization</subfield><subfield code="2">Elsevier</subfield></datafield><datafield tag="650" ind1=" " ind2="7"><subfield code="a">Soluble polymer supports</subfield><subfield code="2">Elsevier</subfield></datafield><datafield tag="650" ind1=" " ind2="7"><subfield code="a">Atom transfer radical polymerization</subfield><subfield code="2">Elsevier</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Trinh, Thanh Tam</subfield><subfield code="4">oth</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Chan-Seng, Delphine</subfield><subfield code="4">oth</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Lutz, Jean-François</subfield><subfield code="4">oth</subfield></datafield><datafield tag="773" ind1="0" ind2="8"><subfield code="i">Enthalten in</subfield><subfield code="n">Elsevier Science</subfield><subfield code="a">Fitzgerald, Emily ELSEVIER</subfield><subfield code="t">Functional outcomes at 12 months for patients with traumatic brain injury, intracerebral haemorrhage and subarachnoid haemorrhage treated in an Australian neurocritical care unit: A prospective cohort study</subfield><subfield code="d">2020</subfield><subfield code="d">the international journal for the science and technology of polymers</subfield><subfield code="g">Oxford</subfield><subfield code="w">(DE-627)ELV005093368</subfield></datafield><datafield tag="773" ind1="1" ind2="8"><subfield code="g">volume:72</subfield><subfield code="g">year:2015</subfield><subfield code="g">day:18</subfield><subfield code="g">month:08</subfield><subfield code="g">pages:341-347</subfield><subfield code="g">extent:7</subfield></datafield><datafield tag="856" ind1="4" ind2="0"><subfield code="u">https://doi.org/10.1016/j.polymer.2015.02.057</subfield><subfield code="3">Volltext</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_USEFLAG_U</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ELV</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">SYSFLAG_U</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">SSG-OLC-PHA</subfield></datafield><datafield tag="936" ind1="b" ind2="k"><subfield code="a">44.63</subfield><subfield code="j">Krankenpflege</subfield><subfield code="q">VZ</subfield></datafield><datafield tag="936" ind1="b" ind2="k"><subfield code="a">44.69</subfield><subfield code="j">Intensivmedizin</subfield><subfield code="q">VZ</subfield></datafield><datafield tag="951" ind1=" " ind2=" "><subfield code="a">AR</subfield></datafield><datafield tag="952" ind1=" " ind2=" "><subfield code="d">72</subfield><subfield code="j">2015</subfield><subfield code="b">18</subfield><subfield code="c">0818</subfield><subfield code="h">341-347</subfield><subfield code="g">7</subfield></datafield></record></collection>
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