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

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

18 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

Publisher Copyright:
© 2016 American Chemical Society.

Funding

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.

Funders	Funder number
National Science Foundation (NSF)	ECCS 1254757, 1254757
Office of Naval Research	N00014-12-1-1007

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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AU - Mei, Yaochuan

AU - Thorley, Karl J.

AU - Parkin, Sean R.

AU - Jurchescu, Oana D.

AU - Anthony, John E.

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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

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Funding

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