2,6-Diarylethynylanthracenes: Synthesis, morphology, and electro-optical properties

Bhanupriya Khanna; Sean R. Parkin; Kevin D. Revell

doi:10.1016/j.tetlet.2012.09.036

2,6-Diarylethynylanthracenes: Synthesis, morphology, and electro-optical properties

Bhanupriya Khanna, Sean R. Parkin, Kevin D. Revell

Chemistry

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

6 Scopus citations

Abstract

A series of 2,6-diarylethynyl-9,10-dialkoxyanthracenes have been synthesized, characterized, and evaluated for their morphological and electro-optical properties. Compounds with 2′-naphthyl and 2′-anthracyl peripheral substituents were found to have poor solubility, and were not explored in detail. However, compounds bearing 9′-anthracyl peripheral substituents exhibited better solubility, and a series of these compounds containing straight-chain and branched substituents were prepared and analyzed. These compounds were found to undergo two oxidations at +0.57 V and +0.76 V relative to a Fc/Fc ⁺ reference. The compounds exhibited absorption with a λ _onset of 510 nm. Based on this, the average solution-phase HOMO-LUMO energies of these compounds were estimated to be -5.37 eV and -2.94 eV, respectively. The compounds exhibited fluorescent behavior, with an emission maximum at 505 nm. Hexoxy and Isobutoxy substituents were optimal for large crystal formation, and crystallographic studies on these two compounds show a herringbone-type arrangement with 1-dimensional pi-stacking.

Original language	English
Pages (from-to)	6383-6387
Number of pages	5
Journal	Tetrahedron Letters
Volume	53
Issue number	47
DOIs	https://doi.org/10.1016/j.tetlet.2012.09.036
State	Published - Nov 21 2012

Bibliographical note

Funding Information:
This material is based upon work supported by the Kentucky NASA EPSCoR program, by the National Science Foundation under CHE-0922033, by the Jones/Ross Research Center at Murray State University, and by the Murray State University Committee on Institutional Research. X-ray data were collected using both a Nonius KappaCCD diffractometer and a Bruker Nonius X8 Proteum diffractometer obtained with funding from the NSF (MRI grant No. 0319176 ). The authors also wish to thank Daniel Johnson (Murray State University) for his assistance with the electrochemical and photoluminescence analyses.

Keywords

Alkynes
Chromophores
Cross-coupling
Semiconductors

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2012.09.036

Cite this

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title = "2,6-Diarylethynylanthracenes: Synthesis, morphology, and electro-optical properties",

abstract = "A series of 2,6-diarylethynyl-9,10-dialkoxyanthracenes have been synthesized, characterized, and evaluated for their morphological and electro-optical properties. Compounds with 2′-naphthyl and 2′-anthracyl peripheral substituents were found to have poor solubility, and were not explored in detail. However, compounds bearing 9′-anthracyl peripheral substituents exhibited better solubility, and a series of these compounds containing straight-chain and branched substituents were prepared and analyzed. These compounds were found to undergo two oxidations at +0.57 V and +0.76 V relative to a Fc/Fc + reference. The compounds exhibited absorption with a λ onset of 510 nm. Based on this, the average solution-phase HOMO-LUMO energies of these compounds were estimated to be -5.37 eV and -2.94 eV, respectively. The compounds exhibited fluorescent behavior, with an emission maximum at 505 nm. Hexoxy and Isobutoxy substituents were optimal for large crystal formation, and crystallographic studies on these two compounds show a herringbone-type arrangement with 1-dimensional pi-stacking.",

keywords = "Alkynes, Chromophores, Cross-coupling, Semiconductors",

author = "Bhanupriya Khanna and Parkin, {Sean R.} and Revell, {Kevin D.}",

note = "Funding Information: This material is based upon work supported by the Kentucky NASA EPSCoR program, by the National Science Foundation under CHE-0922033, by the Jones/Ross Research Center at Murray State University, and by the Murray State University Committee on Institutional Research. X-ray data were collected using both a Nonius KappaCCD diffractometer and a Bruker Nonius X8 Proteum diffractometer obtained with funding from the NSF (MRI grant No. 0319176 ). The authors also wish to thank Daniel Johnson (Murray State University) for his assistance with the electrochemical and photoluminescence analyses. ",

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AU - Khanna, Bhanupriya

AU - Parkin, Sean R.

AU - Revell, Kevin D.

N1 - Funding Information: This material is based upon work supported by the Kentucky NASA EPSCoR program, by the National Science Foundation under CHE-0922033, by the Jones/Ross Research Center at Murray State University, and by the Murray State University Committee on Institutional Research. X-ray data were collected using both a Nonius KappaCCD diffractometer and a Bruker Nonius X8 Proteum diffractometer obtained with funding from the NSF (MRI grant No. 0319176 ). The authors also wish to thank Daniel Johnson (Murray State University) for his assistance with the electrochemical and photoluminescence analyses.

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N2 - A series of 2,6-diarylethynyl-9,10-dialkoxyanthracenes have been synthesized, characterized, and evaluated for their morphological and electro-optical properties. Compounds with 2′-naphthyl and 2′-anthracyl peripheral substituents were found to have poor solubility, and were not explored in detail. However, compounds bearing 9′-anthracyl peripheral substituents exhibited better solubility, and a series of these compounds containing straight-chain and branched substituents were prepared and analyzed. These compounds were found to undergo two oxidations at +0.57 V and +0.76 V relative to a Fc/Fc + reference. The compounds exhibited absorption with a λ onset of 510 nm. Based on this, the average solution-phase HOMO-LUMO energies of these compounds were estimated to be -5.37 eV and -2.94 eV, respectively. The compounds exhibited fluorescent behavior, with an emission maximum at 505 nm. Hexoxy and Isobutoxy substituents were optimal for large crystal formation, and crystallographic studies on these two compounds show a herringbone-type arrangement with 1-dimensional pi-stacking.

AB - A series of 2,6-diarylethynyl-9,10-dialkoxyanthracenes have been synthesized, characterized, and evaluated for their morphological and electro-optical properties. Compounds with 2′-naphthyl and 2′-anthracyl peripheral substituents were found to have poor solubility, and were not explored in detail. However, compounds bearing 9′-anthracyl peripheral substituents exhibited better solubility, and a series of these compounds containing straight-chain and branched substituents were prepared and analyzed. These compounds were found to undergo two oxidations at +0.57 V and +0.76 V relative to a Fc/Fc + reference. The compounds exhibited absorption with a λ onset of 510 nm. Based on this, the average solution-phase HOMO-LUMO energies of these compounds were estimated to be -5.37 eV and -2.94 eV, respectively. The compounds exhibited fluorescent behavior, with an emission maximum at 505 nm. Hexoxy and Isobutoxy substituents were optimal for large crystal formation, and crystallographic studies on these two compounds show a herringbone-type arrangement with 1-dimensional pi-stacking.

KW - Alkynes

KW - Chromophores

KW - Cross-coupling

KW - Semiconductors

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2,6-Diarylethynylanthracenes: Synthesis, morphology, and electro-optical properties

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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