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Facile, Efficient Routes to Diverse Protected Thiols and to Their Deprotection and Addition to Create Functional Polymers by Thiol−Ene Coupling

Ameri David, R. L. and Kornfield, Julia A. (2008) Facile, Efficient Routes to Diverse Protected Thiols and to Their Deprotection and Addition to Create Functional Polymers by Thiol−Ene Coupling. Macromolecules, 41 (4). pp. 1151-1161. ISSN 0024-9297. https://resolver.caltech.edu/CaltechAUTHORS:20170605-161033934

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Abstract

Carbazole, dinitrobenzoate, phenol, pyridine, and 4-cyano-4‘-alkoxybiphenyl side groups were grafted onto pendant vinyl groups of polybutadiene (PB) by thiol−ene addition to yield functional polymer of polydispersity equal to that of the precursor material. Synthesis protocols that are clean (>90% conversion to desired product) and scalable were developed to incorporate a protected thiol group into functional precursors. The resulting acetyl or benzoyl thioesters are suitable for long-term storage, and are conveniently deprotected and added to polymer in a matter of hours in a straightforward procedure that does not require isolation of the thiol intermediate. Alternatively, PB functionalization could be achieved with equal success by reaction with β-mercaptoethanol (BME), and subsequent esterification of the incorporated hydroxyl groups with a suitable acyl halide. The chemistry described can potentially be applied to add any side group onto any polymer, copolymer, or block copolymer displaying pendant vinyl groups.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ma0718393DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ma0718393PublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/ma0718393PublisherSupporting Information
ORCID:
AuthorORCID
Kornfield, Julia A.0000-0001-6746-8634
Additional Information:© 2008 American Chemical Society. Received August 14, 2007; Revised Manuscript Received November 21, 2007. Publication Date (Web): January 25, 2008. Funding for this research was provided by the Milliken Foundation and the Gates Grubstake Fund at Caltech. We thank Dr. Steven Smith of Procter and Gamble Company for supplying the 1,2-PB precursor materials, as well as Alessa Gambardella and Ming-Hsin Wei for assistance with the synthesis of the protected thiols.
Funders:
Funding AgencyGrant Number
Milliken FoundationUNSPECIFIED
Gates Grubstake FundUNSPECIFIED
Issue or Number:4
Record Number:CaltechAUTHORS:20170605-161033934
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170605-161033934
Official Citation:Facile, Efficient Routes to Diverse Protected Thiols and to Their Deprotection and Addition to Create Functional Polymers by Thiol−Ene Coupling R. L. Ameri David and Julia A. Kornfield Macromolecules 2008 41 (4), 1151-1161 DOI: 10.1021/ma0718393
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:77951
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:06 Jun 2017 18:45
Last Modified:03 Oct 2019 18:03

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