Efficient synthesis and conformational investigations of cis-pentacenediols

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

Research output: Contribution to journalArticle

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 languageEnglish (US)
Pages (from-to)5732-5735
Number of pages4
JournalTetrahedron Letters
Volume51
Issue number43
DOIs
StatePublished - Oct 2 2010

Keywords

  • Diisobutylaluminum hydride
  • Low-temperature NMR
  • Pentacene
  • Pentacenediol
  • Reduction of pentacenedione

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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