Issue 14, 2014

Bis(5-alkylthiophen-2-yl)arene liquid crystals as molecular semiconductors

Abstract

Mesogens with a general structure bis(alkylthiophene)arene, in which the central arene moiety is 1,4-benzene, 2,5-pyridine, 3,6-pyrimidine, 2,6-naphthalene and 2,6-dithieno[3,2-b;2′,3′-d]thiophene, were synthesized, and the effect of the central unit and the length of the alkyl chains on the liquid crystalline behavior was studied by differential scanning calorimetry and polarized optical microscopy, and in the case of 1,4-bis(5-tridecylthiophen-2-yl)benzene (2a) and 2,6-bis(5-tridecylthiophen-2-yl)DTT by synchrotron X-ray analysis. Several 2,5-bis(5-alkylthiophen-2-yl)pyridines and 1,4-bis(5-tridecylthiophen-2-yl)benzene 2a exhibit a rare transition – formation of the SmF phase directly from the isotropic liquid; in the case of 2a, formation of higher ordered smectic phases was observed on further cooling. Hole-transporting properties of 2a in different mesophases were studied by the time-of-flight technique. The hole mobility, μh, in SmF reached 6 × 10−3 cm2 V−1 s−1 and increased with an increase of the order of the mesophase up to 0.02 cm2 V−1 s−1 in the S1 phase (tentatively assigned as the crystal G phase), ∼0.09 cm2 V−1 s−1 in the S2 phase (tentatively assigned as the crystal H phase), and 0.11 cm2 V−1 s−1 in the crystalline phase at 70 °C.

Graphical abstract: Bis(5-alkylthiophen-2-yl)arene liquid crystals as molecular semiconductors

Supplementary files

Article information

Article type
Paper
Submitted
10 Nov 2013
Accepted
19 Jan 2014
First published
03 Mar 2014

J. Mater. Chem. C, 2014,2, 2600-2611

Bis(5-alkylthiophen-2-yl)arene liquid crystals as molecular semiconductors

Y. A. Getmanenko, S. Kang, N. Shakya, C. Pokhrel, S. D. Bunge, S. Kumar, B. D. Ellman and R. J. Twieg, J. Mater. Chem. C, 2014, 2, 2600 DOI: 10.1039/C3TC32211D

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements