Synthesis, optical, thermal, and redox properties of 2,3,9,10- tetrasubstituted- 6,13-dialkynylpentacenes

John E. Anthony; Christopher R. Swartz; Chad A. Landis; Sean R. Parkin

doi:10.1117/12.615939

Synthesis, optical, thermal, and redox properties of 2,3,9,10- tetrasubstituted- 6,13-dialkynylpentacenes

John E. Anthony, Christopher R. Swartz, Chad A. Landis, Sean R. Parkin

Research output: Contribution to journal › Conference article › peer-review

4 Scopus citations

Abstract

A series of 2,3,9,10-tetrasubstituted-6,13-dialkynylpentacenes was synthesized and their properties evaluated. Various alkynes with different substituents were chosen to explore the effects of substitution on acene properties. The addition of alkyl groups to the pentacene 2,3,9,10-positions showed significant effects on the absorption, emission, and redox properties versus the non-alkylated (R = H) materials. The acenes exhibited excellent solubility in numerous solvents, and HOMO energy levels matched well with the work function of gold, an important electrode material. Crystallographic characterization of the methoxymethylene derivative showed it to adopt a 1 -dimensional π-stacked arrangement, with good overlap of the aromatic faces.

Original language	English
Article number	594002
Pages (from-to)	1-12
Number of pages	12
Journal	Proceedings of SPIE - The International Society for Optical Engineering
Volume	5940
DOIs	https://doi.org/10.1117/12.615939
State	Published - 2005
Event	Organic Field-Effect Transistors IV - San Diego, CA, United States Duration: Jul 31 2005 → Aug 2 2005

ASJC Scopus subject areas

Electronic, Optical and Magnetic Materials
Condensed Matter Physics
Computer Science Applications
Applied Mathematics
Electrical and Electronic Engineering

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title = "Synthesis, optical, thermal, and redox properties of 2,3,9,10- tetrasubstituted- 6,13-dialkynylpentacenes",

abstract = "A series of 2,3,9,10-tetrasubstituted-6,13-dialkynylpentacenes was synthesized and their properties evaluated. Various alkynes with different substituents were chosen to explore the effects of substitution on acene properties. The addition of alkyl groups to the pentacene 2,3,9,10-positions showed significant effects on the absorption, emission, and redox properties versus the non-alkylated (R = H) materials. The acenes exhibited excellent solubility in numerous solvents, and HOMO energy levels matched well with the work function of gold, an important electrode material. Crystallographic characterization of the methoxymethylene derivative showed it to adopt a 1 -dimensional π-stacked arrangement, with good overlap of the aromatic faces.",

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year = "2005",

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note = "Organic Field-Effect Transistors IV ; Conference date: 31-07-2005 Through 02-08-2005",

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T1 - Synthesis, optical, thermal, and redox properties of 2,3,9,10- tetrasubstituted- 6,13-dialkynylpentacenes

AU - Anthony, John E.

AU - Swartz, Christopher R.

AU - Landis, Chad A.

AU - Parkin, Sean R.

PY - 2005

Y1 - 2005

N2 - A series of 2,3,9,10-tetrasubstituted-6,13-dialkynylpentacenes was synthesized and their properties evaluated. Various alkynes with different substituents were chosen to explore the effects of substitution on acene properties. The addition of alkyl groups to the pentacene 2,3,9,10-positions showed significant effects on the absorption, emission, and redox properties versus the non-alkylated (R = H) materials. The acenes exhibited excellent solubility in numerous solvents, and HOMO energy levels matched well with the work function of gold, an important electrode material. Crystallographic characterization of the methoxymethylene derivative showed it to adopt a 1 -dimensional π-stacked arrangement, with good overlap of the aromatic faces.

AB - A series of 2,3,9,10-tetrasubstituted-6,13-dialkynylpentacenes was synthesized and their properties evaluated. Various alkynes with different substituents were chosen to explore the effects of substitution on acene properties. The addition of alkyl groups to the pentacene 2,3,9,10-positions showed significant effects on the absorption, emission, and redox properties versus the non-alkylated (R = H) materials. The acenes exhibited excellent solubility in numerous solvents, and HOMO energy levels matched well with the work function of gold, an important electrode material. Crystallographic characterization of the methoxymethylene derivative showed it to adopt a 1 -dimensional π-stacked arrangement, with good overlap of the aromatic faces.

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JO - Proceedings of SPIE - The International Society for Optical Engineering

JF - Proceedings of SPIE - The International Society for Optical Engineering

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T2 - Organic Field-Effect Transistors IV

Y2 - 31 July 2005 through 2 August 2005

ER -

Synthesis, optical, thermal, and redox properties of 2,3,9,10- tetrasubstituted- 6,13-dialkynylpentacenes

Abstract

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