Issue 16, 2013

1,5-, 2,6- and 9,10-distyrylanthracenes as luminescent organic semiconductors


We report the synthesis, molecular and crystal structures, optoelectronic properties and organic field-effect transistor (OFET) studies of three isomeric distyrylanthracene derivatives 2,6-DPSAnt, 1,5-DPSAnt and 9,10-DPSAnt. The analysis of the structure–property relationships reveals that π-conjugation in this series is defined by two competing factors: the co-planarity of the styryl substituents (highest in 2,6-DPSAnt) and the electronic communication through the anthracene core (strongest in 9,10-DPSAnt). The charge-transport properties of the compounds, on the other hand, are primarily controlled by the solid state packing which is more efficient for the linear 2,6-DPSAnt derivative. Accordingly, the highest field-effect mobility (up to 0.75 cm2 V−1 s−1) was measured for 2,6-DPSAnt. Unexpectedly high charge mobility of 1,5-DPSAnt (up to 0.15 cm2 V−1 s−1) was attributed to excellent thin-film morphology (nearly layer-by-layer growth) and favorable molecular packing in the films, different from that found in single crystals. Unfavorable molecular packing and poor film morphology observed for 9,10-DPSAnt predictably led to no transistor properties being observed for this isomer. Both 2,6-DPSAnt and 1,5-DPSAnt afforded light-emitting transistors with green light emission area localized near an electron-injecting electrode.

Graphical abstract: 1,5-, 2,6- and 9,10-distyrylanthracenes as luminescent organic semiconductors

Supplementary files

Article information

Article type
06 Feb 2013
05 Mar 2013
First published
06 Mar 2013
This article is Open Access
Creative Commons BY license

J. Mater. Chem. C, 2013,1, 2817-2825

1,5-, 2,6- and 9,10-distyrylanthracenes as luminescent organic semiconductors

A. Dadvand, W. Sun, A. G. Moiseev, F. Bélanger-Gariépy, F. Rosei, H. Meng and D. F. Perepichka, J. Mater. Chem. C, 2013, 1, 2817 DOI: 10.1039/C3TC30247D

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