First Synthesis of Diindeno[1,2-g:1′,2′-s]rubicene Derivatives and their Evaluation as Semiconductors

Mark Bown; Christopher J. Dunn; Craig M. Forsyth; Peter Kemppinen; Th. Birendra Singh; Melissa A. Skidmore; Kevin N. Winzenberg

doi:10.1071/CH11375

RESEARCH ARTICLE

First Synthesis of Diindeno[1,2-g:1′,2′-s]rubicene Derivatives and their Evaluation as Semiconductors

Mark Bown ^A , Christopher J. Dunn ^A , Craig M. Forsyth ^B , Peter Kemppinen ^A , Th. Birendra Singh ^A , Melissa A. Skidmore ^A ^C and Kevin N. Winzenberg ^A

+ Author Affiliations

- Author Affiliations

^A Ian Wark Laboratory, CSIRO Molecular and Health Technologies, Clayton South, Vic. 3168, Australia.

^B School of Chemistry, Monash University, Clayton, Vic. 3800, Australia.

^C Corresponding author. Email: melissa.skidmore@csiro.au

Australian Journal of Chemistry 65(2) 145-152 https://doi.org/10.1071/CH11375
Submitted: 21 September 2011 Accepted: 7 December 2011 Published: 23 January 2012

Abstract

Solution-processable derivatives 4a–d of the novel diindeno[1,2-g:1′,2′-s]rubicene ring system have been prepared in three steps from 1,5-dichloroanthraquinone. Charge extraction by linearly increasing voltage measurements indicates that 4a–d have bulk mobilities <10^–7 cm² V^–1 s^–1. Consistent with these low mobility values, field-effect transistors fabricated from 4a–d show poor performance. X-ray crystallographic analyses indicate that in the crystalline state, molecules of compounds 4b–d pack in a manner that hinders π–π stacking, thus preventing strong electronic coupling between molecules that is essential for high charge mobility semiconductor performance.

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First Synthesis of Diindeno[1,2-g:1′,2′-s]rubicene Derivatives and their Evaluation as Semiconductors

Abstract

References

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