The synthesis and ring-opening metathesis polymerization of an amphiphilic redox-active norbornene

Keith J. Watson; Son Binh T. Nguyen; Chad A. Mirkin

doi:10.1016/S0022-328X(00)00097-8

The synthesis and ring-opening metathesis polymerization of an amphiphilic redox-active norbornene

Keith J. Watson, Son Binh T. Nguyen^*, Chad A. Mirkin

^*Corresponding author for this work

Chemistry

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

27 Scopus citations

Abstract

The synthesis and characterization of an amphiphilic, ferrocenyl-modified norbornene is reported. Linked together through a quaternary ammonium salt, the norbornenyl moiety makes this monomer susceptible to ring-opening metathesis polymerization (ROMP) using (PCy₃)₂RuCl₂=CHPh, while the ferrocenyl group allows for the incorporation of a redox-active group in the polymer backbone. The resulting polymers are soluble in both aqueous and organic media. Such polymers are important for the development of materials for electrochemically-based diagnostic applications. Cyclic voltammetry studies revealed that reversible redox waves are observed for both the monomer and polymer, although the E_1/2 of the polymer is approximately 145 mV lower than that of the monomer, reflecting very different local environments.

Original language	English (US)
Pages (from-to)	79-83
Number of pages	5
Journal	Journal of Organometallic Chemistry
Volume	606
Issue number	1
DOIs	https://doi.org/10.1016/S0022-328X(00)00097-8
State	Published - Jul 14 2000

Keywords

Ferrocene
Metathesis
Norbornene
Polymer
Quaternary ammonium salt

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry
Materials Chemistry

Access to Document

10.1016/S0022-328X(00)00097-8

Cite this

@article{9d9d31d267f04533bf3f87493ade2201,

title = "The synthesis and ring-opening metathesis polymerization of an amphiphilic redox-active norbornene",

abstract = "The synthesis and characterization of an amphiphilic, ferrocenyl-modified norbornene is reported. Linked together through a quaternary ammonium salt, the norbornenyl moiety makes this monomer susceptible to ring-opening metathesis polymerization (ROMP) using (PCy3)2RuCl2=CHPh, while the ferrocenyl group allows for the incorporation of a redox-active group in the polymer backbone. The resulting polymers are soluble in both aqueous and organic media. Such polymers are important for the development of materials for electrochemically-based diagnostic applications. Cyclic voltammetry studies revealed that reversible redox waves are observed for both the monomer and polymer, although the E1/2 of the polymer is approximately 145 mV lower than that of the monomer, reflecting very different local environments.",

keywords = "Ferrocene, Metathesis, Norbornene, Polymer, Quaternary ammonium salt",

author = "Watson, {Keith J.} and Nguyen, {Son Binh T.} and Mirkin, {Chad A.}",

note = "Funding Information: We thank the AFOSR for support of this work. CAM acknowledges support by the NSF and AFSOR. Support by the Beckman Foundation, the Packard Foundation, the Dreyfus Foundation, and the Dupont Company through Young Investigator grants to STN are appreciated. KJW acknowledges the Natural Sciences and Engineering Research Council of Canada (NSERC) for a predoctoral fellowship.",

year = "2000",

month = jul,

day = "14",

doi = "10.1016/S0022-328X(00)00097-8",

language = "English (US)",

volume = "606",

pages = "79--83",

journal = "Journal of Organometallic Chemistry",

issn = "0022-328X",

publisher = "Elsevier",

number = "1",

}

TY - JOUR

T1 - The synthesis and ring-opening metathesis polymerization of an amphiphilic redox-active norbornene

AU - Watson, Keith J.

AU - Nguyen, Son Binh T.

AU - Mirkin, Chad A.

N1 - Funding Information: We thank the AFOSR for support of this work. CAM acknowledges support by the NSF and AFSOR. Support by the Beckman Foundation, the Packard Foundation, the Dreyfus Foundation, and the Dupont Company through Young Investigator grants to STN are appreciated. KJW acknowledges the Natural Sciences and Engineering Research Council of Canada (NSERC) for a predoctoral fellowship.

PY - 2000/7/14

Y1 - 2000/7/14

N2 - The synthesis and characterization of an amphiphilic, ferrocenyl-modified norbornene is reported. Linked together through a quaternary ammonium salt, the norbornenyl moiety makes this monomer susceptible to ring-opening metathesis polymerization (ROMP) using (PCy3)2RuCl2=CHPh, while the ferrocenyl group allows for the incorporation of a redox-active group in the polymer backbone. The resulting polymers are soluble in both aqueous and organic media. Such polymers are important for the development of materials for electrochemically-based diagnostic applications. Cyclic voltammetry studies revealed that reversible redox waves are observed for both the monomer and polymer, although the E1/2 of the polymer is approximately 145 mV lower than that of the monomer, reflecting very different local environments.

AB - The synthesis and characterization of an amphiphilic, ferrocenyl-modified norbornene is reported. Linked together through a quaternary ammonium salt, the norbornenyl moiety makes this monomer susceptible to ring-opening metathesis polymerization (ROMP) using (PCy3)2RuCl2=CHPh, while the ferrocenyl group allows for the incorporation of a redox-active group in the polymer backbone. The resulting polymers are soluble in both aqueous and organic media. Such polymers are important for the development of materials for electrochemically-based diagnostic applications. Cyclic voltammetry studies revealed that reversible redox waves are observed for both the monomer and polymer, although the E1/2 of the polymer is approximately 145 mV lower than that of the monomer, reflecting very different local environments.

KW - Ferrocene

KW - Metathesis

KW - Norbornene

KW - Polymer

KW - Quaternary ammonium salt

UR - http://www.scopus.com/inward/record.url?scp=0003121443&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0003121443&partnerID=8YFLogxK

U2 - 10.1016/S0022-328X(00)00097-8

DO - 10.1016/S0022-328X(00)00097-8

M3 - Article

AN - SCOPUS:0003121443

VL - 606

SP - 79

EP - 83

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

SN - 0022-328X

IS - 1

ER -

The synthesis and ring-opening metathesis polymerization of an amphiphilic redox-active norbornene

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this