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Synthesis of Poly(1,4-naphthylenevinylenes):  Metathesis Polymerization of Benzobarrelenes

Pu, Lin and Wagaman, Michael W. and Grubbs, Robert H. (1996) Synthesis of Poly(1,4-naphthylenevinylenes):  Metathesis Polymerization of Benzobarrelenes. Macromolecules, 29 (4). pp. 1138-1143. ISSN 0024-9297. http://resolver.caltech.edu/CaltechAUTHORS:20180719-143759576

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Abstract

The syntheses of hexyl- and undecyl-substituted benzobarrelenes 10a,b are described. These molecules readily undergo ring-opening metathesis polymerization (ROMP) to generate the corresponding ring-opened polymers 11a,b. Polymers 11a,b can be conveniently converted into alkyl-substituted poly(1,4-naphthylenevinylenes) (PNVs), 13a,b, by oxidizing them using DDQ (2,3-dichloro-5,6-dicyanoquinone). Both 13a and 13b are soluble in organic solvents and are shown by NMR and UV/vis spectroscopy to be fully conjugated. Strong fluorescence is observed for these new materials. Thin films can be prepared by spin-coating chloroform solutions of the conjugated polymers on glass slides. After being doped with an acetonitrile solution of nitrosonium tetrafluoroborate, these polymer films become highly conductive. The conductivities of 13a,b, 6 and 15 S cm^(-1), respectively, are over 2 orders of magnitude higher than that of the insoluble PNV previously prepared by a different precursor route.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://dx.doi.org/10.1021/ma9500143DOIArticle
ORCID:
AuthorORCID
Grubbs, Robert H.0000-0002-0057-7817
Additional Information:© 1996 American Chemical Society. Received January 6, 1995; Revised Manuscript Received November 9, 1995. We would like to thank Christoph D. Karp, Katherine E. Pomykal, and Ashish Bansal for their assistance in measuring polymer conductivities. This work was supported by the Air Force Office of Scientific Research (AFOSR-88-0094).
Funders:
Funding AgencyGrant Number
Air Force Office of Scientific Research (AFOSR)AFOSR-88-0094
Other Numbering System:
Other Numbering System NameOther Numbering System ID
Arnold and Mabel Beckman Laboratories of Chemical Synthesis9034
Record Number:CaltechAUTHORS:20180719-143759576
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20180719-143759576
Official Citation:Synthesis of Poly(1,4-naphthylenevinylenes):  Metathesis Polymerization of Benzobarrelenes Lin Pu, Michael W. Wagaman, and Robert H. Grubbs Macromolecules 1996 29 (4), 1138-1143 DOI: 10.1021/ma9500143
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:88017
Collection:CaltechAUTHORS
Deposited By: George Porter
Deposited On:19 Jul 2018 22:08
Last Modified:19 Jul 2018 22:08

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