Issue 27, 2014

Structure–properties relationship of carbazole and fluorene hybrid trimers: experimental and theoretical approaches

Abstract

Synthesis and properties of fluorene and carbazole derivatives having three electrophores per molecule with different architectures are reported. The synthesized compounds possess high thermal stabilities with 5% weight loss temperatures exceeding 350 °C. They form glasses with glass transition temperatures ranging from 60 to 68 °C. Cyclovoltammetric experiments revealed the high electrochemical stability of the fluorene trimer. In contrast, 2- and 2,7-fluorenyl substituted carbazole derivatives show irreversible oxidation in the CV experiments. The electron photoemission spectra of the films of the synthesized compounds revealed ionization potentials of 5.65–5.89 eV. Hole drift mobilities in the amorphous layers of the synthesized compounds reach 10−2 cm2 V−1 s−1 at high electric fields, as established by a xerographic time-of-flight technique. DFT calculations show that HOMO and LUMO orbitals of the compounds are very similar in energy and shape. The similar hole mobilities observed for the three compounds are discussed in the frame of the Marcus theory. An important influence of the alkyl groups on the ionization potentials and on the hole mobilities was also observed and its origin is discussed.

Graphical abstract: Structure–properties relationship of carbazole and fluorene hybrid trimers: experimental and theoretical approaches

Supplementary files

Article information

Article type
Paper
Submitted
20 Jan 2014
Accepted
28 Apr 2014
First published
05 Jun 2014

Phys. Chem. Chem. Phys., 2014,16, 13932-13942

Structure–properties relationship of carbazole and fluorene hybrid trimers: experimental and theoretical approaches

A. Tomkeviciene, J. V. Grazulevicius, D. Volyniuk, V. Jankauskas and G. Sini, Phys. Chem. Chem. Phys., 2014, 16, 13932 DOI: 10.1039/C4CP00302K

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