Efficient synthesis and conformational investigations of cis-pentacenediols

Research output: Journal Publications and ReviewsRGC 21 - Publication in refereed journalpeer-review

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Author(s)

  • Jinyue Jiang
  • Charles E. Schiaffo
  • Chris P. Schwartz
  • Yong Pei
  • Joseph J. Dumais
  • Patrick H. Dussault
  • Li Tan

Detail(s)

Original languageEnglish
Pages (from-to)5732-5735
Journal / PublicationTetrahedron Letters
Volume51
Issue number43
Publication statusPublished - 2 Oct 2010
Externally publishedYes

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. © 2010 Elsevier Ltd. All rights reserved.

Research Area(s)

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

Bibliographic Note

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Citation Format(s)

Efficient synthesis and conformational investigations of cis-pentacenediols. / Jiang, Jinyue; Schiaffo, Charles E.; Schwartz, Chris P. et al.
In: Tetrahedron Letters, Vol. 51, No. 43, 02.10.2010, p. 5732-5735.

Research output: Journal Publications and ReviewsRGC 21 - Publication in refereed journalpeer-review