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Synthesis of End-Functionalized Poly(norbornene)s via Ring-Opening Metathesis Polymerization

Bielawski, Christopher W. and Benitez, Diego and Morita, Takeharu and Grubbs, Robert H. (2001) Synthesis of End-Functionalized Poly(norbornene)s via Ring-Opening Metathesis Polymerization. Macromolecules, 34 (25). pp. 8610-8618. ISSN 0024-9297. https://resolver.caltech.edu/CaltechAUTHORS:20170720-074304395

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Abstract

The synthesis of a variety of poly(norbornene)s (PNB)s bearing acetoxy, hydroxy, and vinyl end groups was accomplished. PNBs with an acetoxy group at one terminus and a vinyl group at the other were prepared using norbornene, ruthenium-based olefin metathesis catalyst (PCy_3)_2Cl_2Ru═CHPh, and allyl acetate as a chain transfer agent (CTA). Employing a more active catalyst, (1,3-dimesityl-4,5-dihydroimidazol-2-ylidene)(PCy_3)Cl_2Ru═CHPh, and 1,4-diacetoxy-2-butene as the CTA afforded telechelic PNBs bearing acetoxy groups at both ends of the polymer chains. Molecular weights were controlled by varying the initial monomer/CTA ratio and were in agreement with their theoretical values. Using a similar procedure, acetoxy end-terminated PNBs were also obtained by degradation of high molecular weight PNB. Removal of the acetoxy groups afforded the corresponding hydroxy-terminated polymers with number-averaged functionalities close to two. Mechanisms are proposed for the formation of the end-functionalized polymers. Correction factors for characterizing PNBs by gel permeation chromatography (GPC) are also suggested.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ma010878qDOIArticle
http://pubs.acs.org/doi/abs/10.1021/ma010878qPublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/ma010878qPublisherSupporting Information
ORCID:
AuthorORCID
Bielawski, Christopher W.0000-0002-0520-1982
Grubbs, Robert H.0000-0002-0057-7817
Additional Information:© 2001 American Chemical Society. Received 21 May 2001. Published online 7 November 2001. Published in print 1 December 2001. C.B. gratefully acknowledges the NSF for a predoctoral fellowship. T.M. thanks the Seksui Corporation (Japan) for financial support.
Funders:
Funding AgencyGrant Number
NSFUNSPECIFIED
Seksui CorporationUNSPECIFIED
Issue or Number:25
Record Number:CaltechAUTHORS:20170720-074304395
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170720-074304395
Official Citation:Synthesis of End-Functionalized Poly(norbornene)s via Ring-Opening Metathesis Polymerization Christopher W. Bielawski, Diego Benitez, Takeharu Morita, and Robert H. Grubbs Macromolecules 2001 34 (25), 8610-8618 DOI: 10.1021/ma010878q
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:79230
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:20 Jul 2017 18:34
Last Modified:03 Oct 2019 18:17

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