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

doi:10.1016/j.tetlet.2010.08.080

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^*

^*Corresponding author for this work

Research output: Journal Publications and Reviews › RGC 21 - Publication in refereed journal › peer-review

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.

Original language	English
Pages (from-to)	5732-5735
Journal	Tetrahedron Letters
Volume	51
Issue number	43
DOIs	https://doi.org/10.1016/j.tetlet.2010.08.080
Publication status	Published - 2 Oct 2010
Externally published	Yes

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Publication details (e.g. title, author(s), publication statuses and dates) are captured on an “AS IS” and “AS AVAILABLE” basis at the time of record harvesting from the data source. Suggestions for further amendments or supplementary information can be sent to [email protected].

Research Keywords

Diisobutylaluminum hydride
Low-temperature NMR
Pentacene
Pentacenediol
Reduction of pentacenedione

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title = "Efficient synthesis and conformational investigations of cis-pentacenediols",

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. {\textcopyright} 2010 Elsevier Ltd. All rights reserved.",

keywords = "Diisobutylaluminum hydride, Low-temperature NMR, Pentacene, Pentacenediol, Reduction of pentacenedione",

author = "Jinyue Jiang and Schiaffo, {Charles E.} and Schwartz, {Chris P.} and Yong Pei and Dumais, {Joseph J.} and Zeng, {Xiao Cheng} and Dussault, {Patrick H.} and Li Tan",

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T1 - Efficient synthesis and conformational investigations of cis-pentacenediols

AU - Jiang, Jinyue

AU - Schiaffo, Charles E.

AU - Schwartz, Chris P.

AU - Pei, Yong

AU - Dumais, Joseph J.

AU - Zeng, Xiao Cheng

AU - Dussault, Patrick H.

AU - Tan, Li

N1 - Publication details (e.g. title, author(s), publication statuses and dates) are captured on an “AS IS” and “AS AVAILABLE” basis at the time of record harvesting from the data source. Suggestions for further amendments or supplementary information can be sent to [email protected].

PY - 2010/10/2

Y1 - 2010/10/2

N2 - 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.

AB - 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.

KW - Diisobutylaluminum hydride

KW - Low-temperature NMR

KW - Pentacene

KW - Pentacenediol

KW - Reduction of pentacenedione

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U2 - 10.1016/j.tetlet.2010.08.080

DO - 10.1016/j.tetlet.2010.08.080

M3 - RGC 21 - Publication in refereed journal

SN - 0040-4039

VL - 51

SP - 5732

EP - 5735

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 43

ER -

Efficient synthesis and conformational investigations of cis-pentacenediols

Abstract

Bibliographical note

Research Keywords

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