Efficient synthesis and conformational investigations of cis-pentacenediols

TETRAHEDRON LETTERS

卷:51

Article

Jiang, Jinyue^1,2  Schiaffo, Charles E.³  Schwartz, Chris P.³  Pei, Yong³  Dumais, Joseph J.³  Zeng, Xiao Cheng³  Dussault, Patrick H.³  Tan, Li^1,2 

[1] Univ Nebraska, Dept Mech Engn, Lincoln, NE 68588 USA

[2] Univ Nebraska, Nebraska Ctr Mat & Nanosci, Lincoln, NE 68588 USA

[3] Univ Nebraska, Dept Chem, Lincoln, NE 68588 USA

关键词: Pentacene;    Pentacenediol;    Reduction of pentacenedione;    Diisobutylaluminum hydride;    Low-temperature NMR;   

DOI  :  10.1016/j.tetlet.2010.08.080

来源: Elsevier

【 摘 要 】

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. Published by Elsevier Ltd.

【 授权许可】

Free