Efficient synthesis and conformational investigations of cis-pentacenediols

Authors

Jinyue Jiang, University of Nebraska - LincolnFollow
Charles E. Schiaffo, University of Nebraska–Lincoln
Chris P. Schwartz, University of Nebraska–Lincoln
Yong Pei, University of Nebraska–Lincoln
Joseph J. Dumais, University of Nebraska–Lincoln
Xiao Cheng Zeng, University of Nebraska-LincolnFollow
Patrick Dussault, University of Nebraska-LincolnFollow
Li Tan, University of Nebraska-LincolnFollow

Document Type

Article

Date of this Version

10-2010

Citation

Tetrahedron Letters 51:43 (October 27, 2010), pp. 5732–5735; doi:10.1016/j.tetlet.2010.08.080

Comments

Published by Elsevier Ltd. Used by permission.

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.