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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
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 http://dx.doi.org/10.1071/CH11375
Submitted: 21 September 2011 Accepted: 7 December 2011 Published:
23
January
2012
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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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