Synthesis and Electrical Properties of Derivatives of 1,4-bis(trialkylsilylethynyl)benzo[2,3-b:5,6-b′]diindolizines

Devin B. Granger; Yaochuan Mei; Karl J. Thorley; Sean R. Parkin; Oana D. Jurchescu; John E. Anthony

doi:10.1021/acs.orglett.6b02991

Synthesis and Electrical Properties of Derivatives of 1,4-bis(trialkylsilylethynyl)benzo[2,3-b:5,6-b′]diindolizines

Devin B. Granger, Yaochuan Mei, Karl J. Thorley, Sean R. Parkin, Oana D. Jurchescu, John E. Anthony

Chemistry

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

17 Scopus citations

Abstract

A new class of nitrogen-containing arene organic semiconductors incorporating fused indolizine units is described. This system, though having a zigzag shape, mimics the electronic properties of its linear analogue pentacene as a result of nitrogen lone pair incorporation into the π-electron system. Solubilizing trialkylsilylethynyl groups were employed to target crystal packing motifs appropriate for field-effect transistor devices. The triethylsilylethynyl derivative yielded hole mobilities of 0.1 cm² V^-1 s^-1 and on/off current ratios of 10⁵.

Original language	English
Pages (from-to)	6050-6053
Number of pages	4
Journal	Organic Letters
Volume	18
Issue number	23
DOIs	https://doi.org/10.1021/acs.orglett.6b02991
State	Published - Dec 2 2016

Bibliographical note

Funding Information:
J.E.A. and D.B.G. thank the Office of Naval Research (N00014-12-1-1007) for support of the synthesis and characterization of new organic semiconductors. The device work was supported by the National Science Foundation under Grant ECCS 1254757.

Publisher Copyright:
© 2016 American Chemical Society.

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Synthesis and Electrical Properties of Derivatives of 1,4-bis(trialkylsilylethynyl)benzo[2,3-b:5,6-b′]diindolizines",

abstract = "A new class of nitrogen-containing arene organic semiconductors incorporating fused indolizine units is described. This system, though having a zigzag shape, mimics the electronic properties of its linear analogue pentacene as a result of nitrogen lone pair incorporation into the π-electron system. Solubilizing trialkylsilylethynyl groups were employed to target crystal packing motifs appropriate for field-effect transistor devices. The triethylsilylethynyl derivative yielded hole mobilities of 0.1 cm2 V-1 s-1 and on/off current ratios of 105.",

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doi = "10.1021/acs.orglett.6b02991",

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AU - Granger, Devin B.

AU - Mei, Yaochuan

AU - Thorley, Karl J.

AU - Parkin, Sean R.

AU - Jurchescu, Oana D.

AU - Anthony, John E.

N1 - Funding Information: J.E.A. and D.B.G. thank the Office of Naval Research (N00014-12-1-1007) for support of the synthesis and characterization of new organic semiconductors. The device work was supported by the National Science Foundation under Grant ECCS 1254757. Publisher Copyright: © 2016 American Chemical Society.

PY - 2016/12/2

Y1 - 2016/12/2

N2 - A new class of nitrogen-containing arene organic semiconductors incorporating fused indolizine units is described. This system, though having a zigzag shape, mimics the electronic properties of its linear analogue pentacene as a result of nitrogen lone pair incorporation into the π-electron system. Solubilizing trialkylsilylethynyl groups were employed to target crystal packing motifs appropriate for field-effect transistor devices. The triethylsilylethynyl derivative yielded hole mobilities of 0.1 cm2 V-1 s-1 and on/off current ratios of 105.

AB - A new class of nitrogen-containing arene organic semiconductors incorporating fused indolizine units is described. This system, though having a zigzag shape, mimics the electronic properties of its linear analogue pentacene as a result of nitrogen lone pair incorporation into the π-electron system. Solubilizing trialkylsilylethynyl groups were employed to target crystal packing motifs appropriate for field-effect transistor devices. The triethylsilylethynyl derivative yielded hole mobilities of 0.1 cm2 V-1 s-1 and on/off current ratios of 105.

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Synthesis and Electrical Properties of Derivatives of 1,4-bis(trialkylsilylethynyl)benzo[2,3-b:5,6-b′]diindolizines

Abstract

Bibliographical note

ASJC Scopus subject areas

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