Abstract
Diisobutylaluminum hydride is utilized to reduce pentacene-6,13-diones to the corresponding diols, useful precursors to functionalized pentacenes. This pathway is mild and efficient, and produces the cis-diols as major products. Further, we found the cis-diols adopt endo conformation, which cannot flip to the exo conformation under ambient conditions. Due to the cis and endo orientation, the cis-diols can be potential bidentates in catalysis, molecular propellers, and optoelectronic devices.
Original language | English (US) |
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Pages (from-to) | 5732-5735 |
Number of pages | 4 |
Journal | Tetrahedron Letters |
Volume | 51 |
Issue number | 43 |
DOIs | |
State | Published - Oct 2 2010 |
Keywords
- Diisobutylaluminum hydride
- Low-temperature NMR
- Pentacene
- Pentacenediol
- Reduction of pentacenedione
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry