Efficient synthesis and conformational investigations of cis-pentacenediols

Jinyue Jiang, Charles E. Schiaffo, Chris P. Schwartz, Yong Pei, Joseph J. Dumais, Xiao C 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

Fingerprint

Catalysis
Conformations
Equipment and Supplies
Propellers
Optoelectronic devices
pentacene
diisobutylaluminum

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Jiang, J., Schiaffo, C. E., Schwartz, C. P., Pei, Y., Dumais, J. J., Zeng, X. C., ... Tan, L. (2010). Efficient synthesis and conformational investigations of cis-pentacenediols. Tetrahedron Letters, 51(43), 5732-5735. https://doi.org/10.1016/j.tetlet.2010.08.080

Efficient synthesis and conformational investigations of cis-pentacenediols. / Jiang, Jinyue; Schiaffo, Charles E.; Schwartz, Chris P.; Pei, Yong; Dumais, Joseph J.; Zeng, Xiao C; Dussault, Patrick H; Tan, Li.

In: Tetrahedron Letters, Vol. 51, No. 43, 02.10.2010, p. 5732-5735.

Research output: Contribution to journalArticle

Jiang, J, Schiaffo, CE, Schwartz, CP, Pei, Y, Dumais, JJ, Zeng, XC, Dussault, PH & Tan, L 2010, 'Efficient synthesis and conformational investigations of cis-pentacenediols', Tetrahedron Letters, vol. 51, no. 43, pp. 5732-5735. https://doi.org/10.1016/j.tetlet.2010.08.080
Jiang, Jinyue ; Schiaffo, Charles E. ; Schwartz, Chris P. ; Pei, Yong ; Dumais, Joseph J. ; Zeng, Xiao C ; Dussault, Patrick H ; Tan, Li. / Efficient synthesis and conformational investigations of cis-pentacenediols. In: Tetrahedron Letters. 2010 ; Vol. 51, No. 43. pp. 5732-5735.
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