Synthesis and electronic properties of a linearly fused anthracene dimer

Evans O. Onyango; Philip Z. Mannes; Alexandre Pletnev; Devin B. Granger; Qianxiang Ai; Chad Risko; John E. Anthony; Gordon W. Gribble

doi:10.1016/j.tetlet.2020.152182

Synthesis and electronic properties of a linearly fused anthracene dimer

Evans O. Onyango
, Philip Z. Mannes
, Alexandre Pletnev
, Devin B. Granger
, Qianxiang Ai
, Chad Risko
, John E. Anthony
, Gordon W. Gribble

Chemistry

Research output: Contribution to journal › Article › peer-review

2 Scopus citations

Abstract

We describe the synthesis and electronic properties of the novel interrupted hexacene 5,16-diphenylcyclobuta[1,2-b:3,4-b′]dianthracene (1). The synthesis is rooted in a sequential twin Sonogashira coupling of 2,3-dibromo-9,10-dihydro-9,10-epoxyanthracene followed by a Vollhardt 2+2+2 cyclotrimerization to give o-bromoaryl(trimethylsilyl) 8, after selective bromination. A Diels-Alder cycloaddition of the aryne from 8 and 1,3-diphenylisobenzofuran gave 1 after deoxygenation. Photophysical studies suggest that the fused cyclobutane ring been the two anthracene rings allows through-conjugation, but does not allow 1 to behave as a conjugated acene. Attempts to synthesize the parent analogue, cyclobuta[1,2-b:3,4-b′]dianthracene (2) were not successful, but detailed calculations are reported for both 1 and 2.

Original language	English
Article number	152182
Journal	Tetrahedron Letters
Volume	61
Issue number	31
DOIs	https://doi.org/10.1016/j.tetlet.2020.152182
State	Published - Jul 30 2020

Bibliographical note

Publisher Copyright:
© 2020 Elsevier Ltd

Funding

GWG acknowledges support by the donors of the Petroleum Research Fund administered by the American Chemical Society. PZM thanks Dartmouth College for a Zabriskie Fellowship. GWG acknowledges support by the donors of the Petroleum Research Fund administered by the American Chemical Society . PZM thanks Dartmouth College for a Zabriskie Fellowship.

Funders
American Chemical Society
American Chemical Society Petroleum Research Fund
Dartmouth College

Keywords

Anthracene
DFT calculations
Diels-Alder cycloaddition
Fused cyclobutanes
Photophysical studies
Polycyclic aromatic hydrocarbons
UV/Vis absorption

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2020.152182

Cite this

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title = "Synthesis and electronic properties of a linearly fused anthracene dimer",

abstract = "We describe the synthesis and electronic properties of the novel interrupted hexacene 5,16-diphenylcyclobuta[1,2-b:3,4-b′]dianthracene (1). The synthesis is rooted in a sequential twin Sonogashira coupling of 2,3-dibromo-9,10-dihydro-9,10-epoxyanthracene followed by a Vollhardt 2+2+2 cyclotrimerization to give o-bromoaryl(trimethylsilyl) 8, after selective bromination. A Diels-Alder cycloaddition of the aryne from 8 and 1,3-diphenylisobenzofuran gave 1 after deoxygenation. Photophysical studies suggest that the fused cyclobutane ring been the two anthracene rings allows through-conjugation, but does not allow 1 to behave as a conjugated acene. Attempts to synthesize the parent analogue, cyclobuta[1,2-b:3,4-b′]dianthracene (2) were not successful, but detailed calculations are reported for both 1 and 2.",

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AU - Onyango, Evans O.

AU - Mannes, Philip Z.

AU - Pletnev, Alexandre

AU - Granger, Devin B.

AU - Ai, Qianxiang

AU - Risko, Chad

AU - Anthony, John E.

AU - Gribble, Gordon W.

PY - 2020/7/30

Y1 - 2020/7/30

N2 - We describe the synthesis and electronic properties of the novel interrupted hexacene 5,16-diphenylcyclobuta[1,2-b:3,4-b′]dianthracene (1). The synthesis is rooted in a sequential twin Sonogashira coupling of 2,3-dibromo-9,10-dihydro-9,10-epoxyanthracene followed by a Vollhardt 2+2+2 cyclotrimerization to give o-bromoaryl(trimethylsilyl) 8, after selective bromination. A Diels-Alder cycloaddition of the aryne from 8 and 1,3-diphenylisobenzofuran gave 1 after deoxygenation. Photophysical studies suggest that the fused cyclobutane ring been the two anthracene rings allows through-conjugation, but does not allow 1 to behave as a conjugated acene. Attempts to synthesize the parent analogue, cyclobuta[1,2-b:3,4-b′]dianthracene (2) were not successful, but detailed calculations are reported for both 1 and 2.

AB - We describe the synthesis and electronic properties of the novel interrupted hexacene 5,16-diphenylcyclobuta[1,2-b:3,4-b′]dianthracene (1). The synthesis is rooted in a sequential twin Sonogashira coupling of 2,3-dibromo-9,10-dihydro-9,10-epoxyanthracene followed by a Vollhardt 2+2+2 cyclotrimerization to give o-bromoaryl(trimethylsilyl) 8, after selective bromination. A Diels-Alder cycloaddition of the aryne from 8 and 1,3-diphenylisobenzofuran gave 1 after deoxygenation. Photophysical studies suggest that the fused cyclobutane ring been the two anthracene rings allows through-conjugation, but does not allow 1 to behave as a conjugated acene. Attempts to synthesize the parent analogue, cyclobuta[1,2-b:3,4-b′]dianthracene (2) were not successful, but detailed calculations are reported for both 1 and 2.

KW - Anthracene

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KW - Diels-Alder cycloaddition

KW - Fused cyclobutanes

KW - Photophysical studies

KW - Polycyclic aromatic hydrocarbons

KW - UV/Vis absorption

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ER -

Synthesis and electronic properties of a linearly fused anthracene dimer

Abstract

Bibliographical note

Funding

Keywords

ASJC Scopus subject areas

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