Orthogonal multifunctionalization of random and alternating copolymers

Niels Ten Brummelhuis, Marcus Weck

Research output: Contribution to journalArticle

Abstract

A series of copolymers with varying degrees of alternation are synthesized by free-radical polymerization from 2,3,4,5,6-pentafluorostyrene (PFS) and propargyl-containing styrene derivatives. The degree of alternation varied with the electronic nature of the styrene derivative: random copolymers were obtained using monomers with electron withdrawing moieties, whereas increasingly alternating copolymers were obtained by increasing the electron donating nature of the substituent. The copolymers could be functionalized in an orthogonal fashion using a nucleophilic substitution (with thiols) to functionalize PFS and the copper-catalyzed 3 + 2 cycloaddition between azides and the alkyne of the propargyl groups. This methodology allows for the facile synthesis of functional alternating copolymers. (Chemical Equation Presented).

Original languageEnglish (US)
Pages (from-to)1216-1218
Number of pages3
JournalACS Macro Letters
Volume1
Issue number10
DOIs
StatePublished - Oct 16 2012

Fingerprint

Copolymers
Styrene
Derivatives
Alkynes
Azides
Cycloaddition
Electrons
Free radical polymerization
Sulfhydryl Compounds
Copper
Substitution reactions
Monomers

ASJC Scopus subject areas

  • Organic Chemistry
  • Materials Chemistry
  • Polymers and Plastics
  • Inorganic Chemistry

Cite this

Orthogonal multifunctionalization of random and alternating copolymers. / Ten Brummelhuis, Niels; Weck, Marcus.

In: ACS Macro Letters, Vol. 1, No. 10, 16.10.2012, p. 1216-1218.

Research output: Contribution to journalArticle

Ten Brummelhuis, Niels ; Weck, Marcus. / Orthogonal multifunctionalization of random and alternating copolymers. In: ACS Macro Letters. 2012 ; Vol. 1, No. 10. pp. 1216-1218.
@article{f440e1f3cb92469c91aef63f9b41ca14,
title = "Orthogonal multifunctionalization of random and alternating copolymers",
abstract = "A series of copolymers with varying degrees of alternation are synthesized by free-radical polymerization from 2,3,4,5,6-pentafluorostyrene (PFS) and propargyl-containing styrene derivatives. The degree of alternation varied with the electronic nature of the styrene derivative: random copolymers were obtained using monomers with electron withdrawing moieties, whereas increasingly alternating copolymers were obtained by increasing the electron donating nature of the substituent. The copolymers could be functionalized in an orthogonal fashion using a nucleophilic substitution (with thiols) to functionalize PFS and the copper-catalyzed 3 + 2 cycloaddition between azides and the alkyne of the propargyl groups. This methodology allows for the facile synthesis of functional alternating copolymers. (Chemical Equation Presented).",
author = "{Ten Brummelhuis}, Niels and Marcus Weck",
year = "2012",
month = "10",
day = "16",
doi = "10.1021/mz300428n",
language = "English (US)",
volume = "1",
pages = "1216--1218",
journal = "ACS Macro Letters",
issn = "2161-1653",
publisher = "American Chemical Society",
number = "10",

}

TY - JOUR

T1 - Orthogonal multifunctionalization of random and alternating copolymers

AU - Ten Brummelhuis, Niels

AU - Weck, Marcus

PY - 2012/10/16

Y1 - 2012/10/16

N2 - A series of copolymers with varying degrees of alternation are synthesized by free-radical polymerization from 2,3,4,5,6-pentafluorostyrene (PFS) and propargyl-containing styrene derivatives. The degree of alternation varied with the electronic nature of the styrene derivative: random copolymers were obtained using monomers with electron withdrawing moieties, whereas increasingly alternating copolymers were obtained by increasing the electron donating nature of the substituent. The copolymers could be functionalized in an orthogonal fashion using a nucleophilic substitution (with thiols) to functionalize PFS and the copper-catalyzed 3 + 2 cycloaddition between azides and the alkyne of the propargyl groups. This methodology allows for the facile synthesis of functional alternating copolymers. (Chemical Equation Presented).

AB - A series of copolymers with varying degrees of alternation are synthesized by free-radical polymerization from 2,3,4,5,6-pentafluorostyrene (PFS) and propargyl-containing styrene derivatives. The degree of alternation varied with the electronic nature of the styrene derivative: random copolymers were obtained using monomers with electron withdrawing moieties, whereas increasingly alternating copolymers were obtained by increasing the electron donating nature of the substituent. The copolymers could be functionalized in an orthogonal fashion using a nucleophilic substitution (with thiols) to functionalize PFS and the copper-catalyzed 3 + 2 cycloaddition between azides and the alkyne of the propargyl groups. This methodology allows for the facile synthesis of functional alternating copolymers. (Chemical Equation Presented).

UR - http://www.scopus.com/inward/record.url?scp=84887097116&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84887097116&partnerID=8YFLogxK

U2 - 10.1021/mz300428n

DO - 10.1021/mz300428n

M3 - Article

VL - 1

SP - 1216

EP - 1218

JO - ACS Macro Letters

JF - ACS Macro Letters

SN - 2161-1653

IS - 10

ER -