Efficient synthesis and conformational investigations of cis-pentacenediols

✍ Scribed by Jinyue Jiang; Charles E. Schiaffo; Chris P. Schwartz; Yong Pei; Joseph J. Dumais; Xiao Cheng Zeng; Patrick H. Dussault; Li Tan

• Book ID: 104098253
• Publisher: Elsevier Science
• Year: 2010
• Tongue: French
• Weight: 550 KB
• Volume: 51
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2010.08.080

✦ Synopsis

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.