Organocatalytic synthesis and post-polymerization functionalization of propargyl-functional poly(carbonate)s

Sarah Tempelaar; Ian A Barker; Vinh Xuan Truong; Daniel J Hall; Laetitia Mespouille; Philippe Dubois; Andrew P Dove

doi:10.1039/c2py20718d

Organocatalytic synthesis and post-polymerization functionalization of propargyl-functional poly(carbonate)s

Sarah Tempelaar, Ian A Barker, Vinh Xuan Truong, Daniel J Hall, Laetitia Mespouille, Philippe Dubois, Andrew P Dove

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

48 Citations (Scopus)

Abstract

The synthesis of well-defined propargyl-functional poly(carbonate)s was achieved via the organocatalytic ring-opening polymerization of 5-methyl-5-propargyloxycarbonyl-1,3-dioxan-2-one (MPC) using the dual catalyst system of 1-(3,5-bis(trifluoromethyl)phenyl)-3-cyclohexylthiourea (TU) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). The resulting homopolymers showed low dispersities and high end-group fidelity, with the versatility of the system being demonstrated by the synthesis of telechelic copolymers and block copolymers. The synthesized homopolymers with varying degree of polymerization were functionalized with a range of azides via copper-catalyzed Huisgen-1,3-dipolar addition or thiols via radical thiylation, to produce functional aliphatic poly(carbonate)s from a single polymeric scaffold

Original language	English
Pages (from-to)	174 - 183
Number of pages	10
Journal	Polymer Chemistry
Volume	4
Issue number	1
DOIs	https://doi.org/10.1039/c2py20718d
Publication status	Published - 2013
Externally published	Yes

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title = "Organocatalytic synthesis and post-polymerization functionalization of propargyl-functional poly(carbonate)s",

abstract = "The synthesis of well-defined propargyl-functional poly(carbonate)s was achieved via the organocatalytic ring-opening polymerization of 5-methyl-5-propargyloxycarbonyl-1,3-dioxan-2-one (MPC) using the dual catalyst system of 1-(3,5-bis(trifluoromethyl)phenyl)-3-cyclohexylthiourea (TU) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). The resulting homopolymers showed low dispersities and high end-group fidelity, with the versatility of the system being demonstrated by the synthesis of telechelic copolymers and block copolymers. The synthesized homopolymers with varying degree of polymerization were functionalized with a range of azides via copper-catalyzed Huisgen-1,3-dipolar addition or thiols via radical thiylation, to produce functional aliphatic poly(carbonate)s from a single polymeric scaffold",

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year = "2013",

doi = "10.1039/c2py20718d",

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volume = "4",

pages = "174 -- 183",

journal = "Polymer Chemistry",

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T1 - Organocatalytic synthesis and post-polymerization functionalization of propargyl-functional poly(carbonate)s

AU - Tempelaar, Sarah

AU - Barker, Ian A

AU - Truong, Vinh Xuan

AU - Hall, Daniel J

AU - Mespouille, Laetitia

AU - Dubois, Philippe

AU - Dove, Andrew P

PY - 2013

Y1 - 2013

N2 - The synthesis of well-defined propargyl-functional poly(carbonate)s was achieved via the organocatalytic ring-opening polymerization of 5-methyl-5-propargyloxycarbonyl-1,3-dioxan-2-one (MPC) using the dual catalyst system of 1-(3,5-bis(trifluoromethyl)phenyl)-3-cyclohexylthiourea (TU) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). The resulting homopolymers showed low dispersities and high end-group fidelity, with the versatility of the system being demonstrated by the synthesis of telechelic copolymers and block copolymers. The synthesized homopolymers with varying degree of polymerization were functionalized with a range of azides via copper-catalyzed Huisgen-1,3-dipolar addition or thiols via radical thiylation, to produce functional aliphatic poly(carbonate)s from a single polymeric scaffold

AB - The synthesis of well-defined propargyl-functional poly(carbonate)s was achieved via the organocatalytic ring-opening polymerization of 5-methyl-5-propargyloxycarbonyl-1,3-dioxan-2-one (MPC) using the dual catalyst system of 1-(3,5-bis(trifluoromethyl)phenyl)-3-cyclohexylthiourea (TU) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). The resulting homopolymers showed low dispersities and high end-group fidelity, with the versatility of the system being demonstrated by the synthesis of telechelic copolymers and block copolymers. The synthesized homopolymers with varying degree of polymerization were functionalized with a range of azides via copper-catalyzed Huisgen-1,3-dipolar addition or thiols via radical thiylation, to produce functional aliphatic poly(carbonate)s from a single polymeric scaffold

UR - https://www.scopus.com/pages/publications/84874425071

U2 - 10.1039/c2py20718d

DO - 10.1039/c2py20718d

M3 - Article

SN - 1759-9954

VL - 4

SP - 174

EP - 183

JO - Polymer Chemistry

JF - Polymer Chemistry

IS - 1

ER -

Organocatalytic synthesis and post-polymerization functionalization of propargyl-functional poly(carbonate)s

Abstract

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