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Issue 6, 2015
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Diindeno[1,2-b:2′,1′-n]perylene: a closed shell related Chichibabin's hydrocarbon, the synthesis, molecular packing, electronic and charge transport properties

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Abstract

Diindeno[1,2-b:2′,1′-n]perylene, a new derivative of the indenoacene family was synthesized, and its electronic, electrochemical, and electrical properties were investigated. This material has a closed shell electronic configuration which corresponds to a quinoidal structure with a low band gap of 1.35 eV. Molecular packing in the single crystal was studied by single-crystal X-ray structural analysis, and this information was subsequently used in the determination of the charge transfer integrals via density functional theory methods. The charge-carrier transport properties of the diindeno[1,2-b:2′,1′-n]perylene-5,12-dione and diindeno[1,2-b:2′,1′-n]perylene derivatives were investigated through the fabrication and characterization of field-effect transistors via both vacuum-deposited and solution-processed films, respectively. Diindeno[1,2-b:2′,1′-n]perylene exhibited a field-effect behaviour with a hole mobility up to 1.7 × 10−3 cm2 V−1 s−1 when the active layer was solution-processed.

Graphical abstract: Diindeno[1,2-b:2′,1′-n]perylene: a closed shell related Chichibabin's hydrocarbon, the synthesis, molecular packing, electronic and charge transport properties

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Article information


Submitted
20 Feb 2015
Accepted
25 Mar 2015
First published
26 Mar 2015

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2015,6, 3402-3409
Article type
Edge Article
Author version available

Diindeno[1,2-b:2′,1′-n]perylene: a closed shell related Chichibabin's hydrocarbon, the synthesis, molecular packing, electronic and charge transport properties

K. Sbargoud, M. Mamada, J. Marrot, S. Tokito, A. Yassar and M. Frigoli, Chem. Sci., 2015, 6, 3402
DOI: 10.1039/C5SC00652J

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