Fast and Complete Neutralization of Thiocarbonylthio Compounds Using Trialkylborane and Oxygen: Application to Their Removal from RAFT-Synthesized Polymers

Prakash Alagi; Nikos Hadjichristidis; Yves Gnanou; Xiaoshuang Feng

doi:10.1021/acsmacrolett.9b00357

Fast and Complete Neutralization of Thiocarbonylthio Compounds Using Trialkylborane and Oxygen: Application to Their Removal from RAFT-Synthesized Polymers

Prakash Alagi, Nikos Hadjichristidis, Yves Gnanou, Xiaoshuang Feng

Research output: Contribution to journal › Article › peer-review

31 Scopus citations

Abstract

A rapid and efficient method to remove thiocarbonylthio end groups from polymers prepared by reversible addition–fragmentation chain transfer (RAFT) is described. The elimination process is obtained in less than 1 min by treating the solution of RAFT-synthesized polymers with 5 equiv of trialkylborane (TAB) in the presence of oxygen under an ambient temperature. The versatility of this method was checked on the most relevant families of thiocarbonylthio chain transfer agents (CTA), including dithioesters, trithiocarbonates, dithiocarbamates, and xanthates, carried by the corresponding RAFT-synthesized polymers. UV, NMR, and MALDI-TOF MS characterization results all confirm the complete removal of their terminal CTA groups.

Original language	English (US)
Pages (from-to)	664-669
Number of pages	6
Journal	ACS Macro Letters
Volume	8
Issue number	6
DOIs	https://doi.org/10.1021/acsmacrolett.9b00357
State	Published - May 24 2019

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledged KAUST grant number(s): BAS/1/1374-01-01
Acknowledgements: This research work is supported by KAUST under baseline funding (BAS/1/1374-01-01).

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10.1021/acsmacrolett.9b00357

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title = "Fast and Complete Neutralization of Thiocarbonylthio Compounds Using Trialkylborane and Oxygen: Application to Their Removal from RAFT-Synthesized Polymers",

abstract = "A rapid and efficient method to remove thiocarbonylthio end groups from polymers prepared by reversible addition–fragmentation chain transfer (RAFT) is described. The elimination process is obtained in less than 1 min by treating the solution of RAFT-synthesized polymers with 5 equiv of trialkylborane (TAB) in the presence of oxygen under an ambient temperature. The versatility of this method was checked on the most relevant families of thiocarbonylthio chain transfer agents (CTA), including dithioesters, trithiocarbonates, dithiocarbamates, and xanthates, carried by the corresponding RAFT-synthesized polymers. UV, NMR, and MALDI-TOF MS characterization results all confirm the complete removal of their terminal CTA groups.",

author = "Prakash Alagi and Nikos Hadjichristidis and Yves Gnanou and Xiaoshuang Feng",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledged KAUST grant number(s): BAS/1/1374-01-01 Acknowledgements: This research work is supported by KAUST under baseline funding (BAS/1/1374-01-01).",

year = "2019",

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doi = "10.1021/acsmacrolett.9b00357",

language = "English (US)",

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T1 - Fast and Complete Neutralization of Thiocarbonylthio Compounds Using Trialkylborane and Oxygen: Application to Their Removal from RAFT-Synthesized Polymers

AU - Alagi, Prakash

AU - Hadjichristidis, Nikos

AU - Gnanou, Yves

AU - Feng, Xiaoshuang

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledged KAUST grant number(s): BAS/1/1374-01-01 Acknowledgements: This research work is supported by KAUST under baseline funding (BAS/1/1374-01-01).

PY - 2019/5/24

Y1 - 2019/5/24

N2 - A rapid and efficient method to remove thiocarbonylthio end groups from polymers prepared by reversible addition–fragmentation chain transfer (RAFT) is described. The elimination process is obtained in less than 1 min by treating the solution of RAFT-synthesized polymers with 5 equiv of trialkylborane (TAB) in the presence of oxygen under an ambient temperature. The versatility of this method was checked on the most relevant families of thiocarbonylthio chain transfer agents (CTA), including dithioesters, trithiocarbonates, dithiocarbamates, and xanthates, carried by the corresponding RAFT-synthesized polymers. UV, NMR, and MALDI-TOF MS characterization results all confirm the complete removal of their terminal CTA groups.

AB - A rapid and efficient method to remove thiocarbonylthio end groups from polymers prepared by reversible addition–fragmentation chain transfer (RAFT) is described. The elimination process is obtained in less than 1 min by treating the solution of RAFT-synthesized polymers with 5 equiv of trialkylborane (TAB) in the presence of oxygen under an ambient temperature. The versatility of this method was checked on the most relevant families of thiocarbonylthio chain transfer agents (CTA), including dithioesters, trithiocarbonates, dithiocarbamates, and xanthates, carried by the corresponding RAFT-synthesized polymers. UV, NMR, and MALDI-TOF MS characterization results all confirm the complete removal of their terminal CTA groups.

UR - http://hdl.handle.net/10754/656100

UR - http://pubs.acs.org/doi/10.1021/acsmacrolett.9b00357

UR - http://www.scopus.com/inward/record.url?scp=85066408963&partnerID=8YFLogxK

U2 - 10.1021/acsmacrolett.9b00357

DO - 10.1021/acsmacrolett.9b00357

M3 - Article

SN - 2161-1653

VL - 8

SP - 664

EP - 669

JO - ACS Macro Letters

JF - ACS Macro Letters

IS - 6

ER -

Fast and Complete Neutralization of Thiocarbonylthio Compounds Using Trialkylborane and Oxygen: Application to Their Removal from RAFT-Synthesized Polymers

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