Kaur, Irvinder and Stein, NN and Kopreski, RP and Miller, GP. (2009) Exploiting Substituent Effects for the Synthesis of a Photooxidatively Resistant Heptacene Derivative. Journal of the American Chemical Society, 131 (10). p. 3424. ISSN 00027863
Full text not available from this repository. (Request a copy)Abstract
Substituent effects have been exploited to produce an unusually persistent heptacene derivative. In total, four new heptacene derivatives with varying levels of photooxidative resistance (1 < 2 < 3 < 4) have been synthesized. A combination of p-(t-butyl)thiophenyl substituents at positions 7 and 16 (i.e., arylthio substituents attached to the most reactive ring) and o-dimethylphenyl substituents at positions 5, 9, 14, and 18 (i.e., steric resistance on neighboring rings) make heptacene derivative 4 especially resistant to photooxidation. It persists for weeks as a solid, for 1-2 days in solution if shielded from tight, and for several hours in solution when directly exposed to both light and air. Heptacene derivative 4 has been fully characterized. It possesses a small HOMO-LUMO gap of 1.37 eV.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | PENTACENE DERIVATIVES; HIGHER ACENES; TETRACENE |
| InterNano Taxonomy: | Nanomanufacturing Processes |
| Collections: | Nanomanufacturing Research Collection |
| Depositing User: | Danielle Federa |
| Date Deposited: | 17 Jun 2009 16:04 |
| Last Modified: | 17 Jun 2009 16:04 |
| URI: | http://eprints.internano.org/id/eprint/126 |
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