Synthesis of Poly(1,4-naphthylenevinylenes): Metathesis Polymerization of Benzobarrelenes
- Creators
- Pu, Lin
- Wagaman, Michael W.
-
Grubbs, Robert H.
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.
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).Additional details
- Eprint ID
- 88017
- DOI
- 10.1021/ma9500143
- Resolver ID
- CaltechAUTHORS:20180719-143759576
- Air Force Office of Scientific Research (AFOSR)
- AFOSR-88-0094
- Created
-
2018-07-19Created from EPrint's datestamp field
- Updated
-
2021-11-16Created from EPrint's last_modified field
- Other Numbering System Name
- Arnold and Mabel Beckman Laboratories of Chemical Synthesis
- Other Numbering System Identifier
- 9034